3D Molecular Geometry Analysis with 2D Graphs

Zhao Xu, Yaochen Xie, Youzhi Luo, Xuan Zhang, Xinyi Xu, Meng Liu, Kaleb Dickerson, Cheng Deng, Maho Nakata, Shuiwang Ji

Main figure for 3D Molecular Geometry Analysis with 2D Graphs

Abstract

Ground-state 3D geometries of molecules are essential for many molecular analysis tasks. Modern quantum mechanical methods can compute accurate 3D geometries but are computationally prohibitive. Currently, an efficient alternative to computing ground-state 3D molecular geometries from 2D graphs is lacking. Here, we propose a novel deep learning framework to predict 3D geometries from molecular graphs. To this end, we develop an equilibrium message passing neural network (EMPNN) to better capture ground-state geometries from molecular graphs. To provide a testbed for 3D molecular geometry analysis, we develop a benchmark that includes a large-scale molecular geometry dataset, data splits, and evaluation protocols. Experimental results show that EMPNN can efficiently predict more accurate ground-state 3D geometries than RDKit and other deep learning methods. Results also show that the proposed framework outperforms self-supervised learning methods on property prediction tasks.

Proposed method: GAP-EMPNN

Benchmark Results

Tested on 2 datasets 1 baseline value reported too low

Tables show presented results in global context (best 3 papers + GCN + MLP).

MoleculeNet

#ModelRMSE ↓Paper
1
Graphormer-SPIS
0.4840 ±0.0050
2
Graphormer-SPD
0.4920 ±0.0040
3
conan-FGW
0.5140 ±0.0190
7
GCN
0.5640 ±0.0150
86
GAP-EMPNN
0.9970 ±0.0270
This paper
98
GraphMVP
actual #98 vs paper #101 3 places worse
1.0910 ±0.0210
best reported
actual #98 vs paper #101 3 places worse
paper 1.1090
paper 1.1090 Δ at pub 0.0180 Δ today 0.0180
104
AM
1.1120
This paper
105
JOAO
1.1200
This paper
115
CP
1.1960
This paper
#ModelRMSE ↓Paper
1
MemGNN
0.5560 ±0.0230
2
ProtoS-L2
0.5800 ±0.0160
3
ProtoW-L2
0.6040 ±0.0140
7
GCN
0.6550 ±0.0360
18
CP
0.7020
This paper
21
JOAO
0.7080
This paper
27
GraphMVP
0.7180
This paper
32
AM
0.7300
This paper
34
GAP-EMPNN
0.7320 ±0.0050
This paper
SOTA performance (not significantly different from the best) Proposed method (this paper) Baseline / comparison (this paper) Global context (other papers) Best at pub — reported result worse than the best known when published (best reported in green)