NPASS Compound

Structure

NPC470387 OpenBabel07101718192D 26 29 0 0 1 0 0 0 0 0999 V2000 2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3997 -1.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 1.0185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0871 -2.8138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2172 1.6034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7148 1.0829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 0.0373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5050 -0.6827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6397 -1.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6182 0.3693 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2579 -0.7014 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8653 0.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0108 -0.7200 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3998 -1.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8868 -1.0520 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2471 0.0187 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8503 1.3879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8477 -1.2329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9127 -2.7839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3999 -1.9404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 4 26 1 0 0 0 0 5 6 1 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 19 1 0 0 0 0 9 14 1 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 5 1 1 0 0 0 13 20 1 6 0 0 0 13 21 1 0 0 0 0 14 19 1 6 0 0 0 14 20 1 0 0 0 0 15 20 1 0 0 0 0 15 22 2 0 0 0 0 16 21 1 1 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 17 24 2 0 0 0 0 18 19 1 0 0 0 0 18 25 2 0 0 0 0 18 26 1 0 0 0 0 19 2 1 1 0 0 0 20 3 1 6 0 0 0 21 10 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.19
Volume:	370.952
LogP:	1.067
LogD:	1.106
LogS:	-3.765
# Rotatable Bonds:	2
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.574
Synthetic Accessibility Score:	5.955
Fsp3:	0.762
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.807
MDCK Permeability:	3.055750494240783e-05
Pgp-inhibitor:	0.97
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.376
30% Bioavailability (F30%):	0.262

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.903
Plasma Protein Binding (PPB):	64.88030242919922%
Volume Distribution (VD):	0.544
Pgp-substrate:	44.032142639160156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.753
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.734
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.254
CYP3A4-inhibitor:	0.583
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	5.773
Half-life (T1/2):	0.675

ADMET: Toxicity

hERG Blockers:	0.135
Human Hepatotoxicity (H-HT):	0.213
Drug-inuced Liver Injury (DILI):	0.081
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.981
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.919
Carcinogencity:	0.907
Eye Corrosion:	0.232
Eye Irritation:	0.175
Respiratory Toxicity:	0.984

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC470387

Natural Product ID:	NPC470387
*Common Name:**	Methylgeopyxin C
IUPAC Name:	n.a.
Synonyms:	Methylgeopyxin C
Standard InCHIKey:	VCVUJQJODGVLDL-ZXQYVARWSA-N
Standard InCHI:	InChI=1S/C21H28O5/c1-11-12-5-6-13-20(3)14(9-16(23)21(13,10-12)17(11)24)19(2,18(25)26-4)8-7-15(20)22/h12-14,16,23H,1,5-10H2,2-4H3/t12-,13+,14-,16+,19-,20+,21-/m1/s1
SMILES:	CC1(CCC(=O)C2(C1CC(C34C2CCC(C3)C(=C)C4=O)O)C)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2022265
PubChem CID:	57380388
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33235	geopyxis sp. az0066	Species	Pyronemataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22264149]
NPO32738	geopyxis aff. majalis	Species	Pyronemataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22264149]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	2280.0	nM	PMID[449031]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	1560.0	nM	PMID[449031]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1670.0	nM	PMID[449031]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	3380.0	nM	PMID[449031]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3630.0	nM	PMID[449031]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC470387 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	1670
0.2-0.3	5821
0.3-0.4	11041
0.4-0.5	9985
0.5-0.6	6123
0.6-0.7	5225
0.7-0.8	2253
0.8-0.85	191
0.85-0.9	109
0.9-0.95	52
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9775	High Similarity	NPC470385
0.9775	High Similarity	NPC470386
0.9667	High Similarity	NPC470232
0.956	High Similarity	NPC329910
0.9556	High Similarity	NPC475118
0.9551	High Similarity	NPC198242
0.9551	High Similarity	NPC211403
0.9451	High Similarity	NPC470229
0.9368	High Similarity	NPC216114
0.9355	High Similarity	NPC471038
0.9341	High Similarity	NPC47853
0.9271	High Similarity	NPC98603
0.9271	High Similarity	NPC84928
0.9255	High Similarity	NPC470388
0.9158	High Similarity	NPC289148
0.9158	High Similarity	NPC71706
0.9158	High Similarity	NPC52899
0.9158	High Similarity	NPC163963
0.9158	High Similarity	NPC46848
0.9149	High Similarity	NPC474793
0.914	High Similarity	NPC200054
0.914	High Similarity	NPC29410
0.9121	High Similarity	NPC470230
0.9121	High Similarity	NPC250753
0.9101	High Similarity	NPC259009
0.9072	High Similarity	NPC474558
0.9062	High Similarity	NPC304832
0.9062	High Similarity	NPC246736
0.9062	High Similarity	NPC214946
0.9062	High Similarity	NPC148628
0.9062	High Similarity	NPC88203
0.9062	High Similarity	NPC76866
0.9062	High Similarity	NPC275990
0.9062	High Similarity	NPC286519
0.9053	High Similarity	NPC287676
0.9032	High Similarity	NPC98639
0.9011	High Similarity	NPC80401
0.8969	High Similarity	NPC277074
0.8969	High Similarity	NPC122811
0.8969	High Similarity	NPC139347
0.8969	High Similarity	NPC87927
0.8969	High Similarity	NPC209298
0.8958	High Similarity	NPC236585
0.8958	High Similarity	NPC471790
0.8947	High Similarity	NPC38296
0.8947	High Similarity	NPC162459
0.8947	High Similarity	NPC16911
0.8947	High Similarity	NPC38471
0.8947	High Similarity	NPC98837
0.8947	High Similarity	NPC78427
0.8947	High Similarity	NPC28864
0.8947	High Similarity	NPC20479
0.8947	High Similarity	NPC89099
0.8936	High Similarity	NPC140242
0.8936	High Similarity	NPC13949
0.8913	High Similarity	NPC476168
0.8901	High Similarity	NPC471043
0.8889	High Similarity	NPC153604
0.8876	High Similarity	NPC190704
0.8876	High Similarity	NPC471034
0.8854	High Similarity	NPC293866
0.8854	High Similarity	NPC267921
0.8842	High Similarity	NPC10864
0.883	High Similarity	NPC266431
0.8817	High Similarity	NPC294263
0.8817	High Similarity	NPC144739
0.8817	High Similarity	NPC181594
0.8788	High Similarity	NPC138908
0.8788	High Similarity	NPC200957
0.8776	High Similarity	NPC96217
0.8763	High Similarity	NPC252614
0.8763	High Similarity	NPC148279
0.8763	High Similarity	NPC295276
0.875	High Similarity	NPC26270
0.8723	High Similarity	NPC302008
0.8723	High Similarity	NPC64006
0.8723	High Similarity	NPC111524
0.8723	High Similarity	NPC292374
0.8723	High Similarity	NPC101233
0.8723	High Similarity	NPC191094
0.8723	High Similarity	NPC153775
0.8723	High Similarity	NPC29247
0.8723	High Similarity	NPC261333
0.8723	High Similarity	NPC215271
0.8723	High Similarity	NPC104371
0.8723	High Similarity	NPC289539
0.8723	High Similarity	NPC129004
0.8723	High Similarity	NPC91772
0.871	High Similarity	NPC299185
0.87	High Similarity	NPC176949
0.87	High Similarity	NPC201908
0.87	High Similarity	NPC186054
0.87	High Similarity	NPC166993
0.8687	High Similarity	NPC202793
0.8673	High Similarity	NPC475803
0.8673	High Similarity	NPC309388
0.866	High Similarity	NPC180733
0.866	High Similarity	NPC55503
0.866	High Similarity	NPC156324
0.866	High Similarity	NPC37047
0.866	High Similarity	NPC41971
0.866	High Similarity	NPC94906
0.8652	High Similarity	NPC291320
0.8652	High Similarity	NPC471036
0.8632	High Similarity	NPC84018
0.8632	High Similarity	NPC138245
0.8632	High Similarity	NPC263135
0.8632	High Similarity	NPC210214
0.8632	High Similarity	NPC288906
0.8632	High Similarity	NPC231060
0.8617	High Similarity	NPC82138
0.8617	High Similarity	NPC224060
0.8617	High Similarity	NPC244356
0.8614	High Similarity	NPC273155
0.8614	High Similarity	NPC231278
0.8614	High Similarity	NPC112895
0.8614	High Similarity	NPC63841
0.8614	High Similarity	NPC218123
0.8602	High Similarity	NPC180849
0.8602	High Similarity	NPC470378
0.8602	High Similarity	NPC261994
0.8602	High Similarity	NPC149761
0.8586	High Similarity	NPC469985
0.8586	High Similarity	NPC159442
0.8571	High Similarity	NPC75941
0.8571	High Similarity	NPC14634
0.8557	High Similarity	NPC288
0.8557	High Similarity	NPC109059
0.8557	High Similarity	NPC472028
0.8556	High Similarity	NPC146683
0.8542	High Similarity	NPC264979
0.8542	High Similarity	NPC104568
0.8542	High Similarity	NPC234564
0.8542	High Similarity	NPC135548
0.8542	High Similarity	NPC219353
0.8515	High Similarity	NPC61071
0.8515	High Similarity	NPC88833
0.8515	High Similarity	NPC96333
0.8515	High Similarity	NPC471474
0.85	High Similarity	NPC13149
0.85	High Similarity	NPC301787
0.85	High Similarity	NPC96268
0.85	High Similarity	NPC101842
0.8485	Intermediate Similarity	NPC124544
0.8485	Intermediate Similarity	NPC272472
0.8478	Intermediate Similarity	NPC174619
0.8462	Intermediate Similarity	NPC473352
0.8454	Intermediate Similarity	NPC96839
0.8454	Intermediate Similarity	NPC253586
0.8447	Intermediate Similarity	NPC471093
0.8444	Intermediate Similarity	NPC118800
0.8431	Intermediate Similarity	NPC471094
0.8431	Intermediate Similarity	NPC232133
0.8431	Intermediate Similarity	NPC469984
0.8431	Intermediate Similarity	NPC211224
0.8431	Intermediate Similarity	NPC473410
0.8421	Intermediate Similarity	NPC59170
0.8421	Intermediate Similarity	NPC59350
0.8416	Intermediate Similarity	NPC164600
0.8416	Intermediate Similarity	NPC295366
0.8416	Intermediate Similarity	NPC222833
0.8416	Intermediate Similarity	NPC56656
0.8416	Intermediate Similarity	NPC4115
0.8416	Intermediate Similarity	NPC12823
0.8416	Intermediate Similarity	NPC103172
0.8416	Intermediate Similarity	NPC37600
0.84	Intermediate Similarity	NPC266
0.84	Intermediate Similarity	NPC470310
0.84	Intermediate Similarity	NPC312900
0.8387	Intermediate Similarity	NPC56413
0.8384	Intermediate Similarity	NPC253886
0.8384	Intermediate Similarity	NPC121218
0.837	Intermediate Similarity	NPC471042
0.8367	Intermediate Similarity	NPC114274
0.8365	Intermediate Similarity	NPC329953
0.8365	Intermediate Similarity	NPC470281
0.8365	Intermediate Similarity	NPC29505
0.835	Intermediate Similarity	NPC469983
0.8316	Intermediate Similarity	NPC476934
0.8316	Intermediate Similarity	NPC278106
0.83	Intermediate Similarity	NPC170615
0.8298	Intermediate Similarity	NPC57954
0.8298	Intermediate Similarity	NPC213832
0.8286	Intermediate Similarity	NPC40608
0.8283	Intermediate Similarity	NPC291785
0.8283	Intermediate Similarity	NPC127408
0.8283	Intermediate Similarity	NPC108371
0.8283	Intermediate Similarity	NPC293890
0.828	Intermediate Similarity	NPC33768
0.828	Intermediate Similarity	NPC165895
0.828	Intermediate Similarity	NPC57469
0.8269	Intermediate Similarity	NPC49730
0.8269	Intermediate Similarity	NPC474786
0.8269	Intermediate Similarity	NPC85391
0.8269	Intermediate Similarity	NPC98069
0.8269	Intermediate Similarity	NPC320383
0.8269	Intermediate Similarity	NPC137104
0.8261	Intermediate Similarity	NPC224345
0.8261	Intermediate Similarity	NPC102292
0.8252	Intermediate Similarity	NPC469733

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC470387 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	2110
0.2-0.3	4013
0.3-0.4	1845
0.4-0.5	517
0.5-0.6	211
0.6-0.7	147
0.7-0.8	108
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8065	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD6079	Approved
0.7755	Intermediate Similarity	NPD8035	Phase 2
0.7755	Intermediate Similarity	NPD8034	Phase 2
0.7732	Intermediate Similarity	NPD5328	Approved
0.7706	Intermediate Similarity	NPD4632	Approved
0.7692	Intermediate Similarity	NPD6115	Approved
0.7692	Intermediate Similarity	NPD6697	Approved
0.7692	Intermediate Similarity	NPD6118	Approved
0.7692	Intermediate Similarity	NPD6114	Approved
0.7647	Intermediate Similarity	NPD7638	Approved
0.7642	Intermediate Similarity	NPD5697	Approved
0.7624	Intermediate Similarity	NPD5221	Approved
0.7624	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD5222	Approved
0.7611	Intermediate Similarity	NPD6319	Approved
0.7576	Intermediate Similarity	NPD7515	Phase 2
0.7573	Intermediate Similarity	NPD7640	Approved
0.7573	Intermediate Similarity	NPD7639	Approved
0.757	Intermediate Similarity	NPD6881	Approved
0.757	Intermediate Similarity	NPD6899	Approved
0.757	Intermediate Similarity	NPD6011	Approved
0.7556	Intermediate Similarity	NPD3703	Phase 2
0.7549	Intermediate Similarity	NPD5173	Approved
0.7547	Intermediate Similarity	NPD5739	Approved
0.7547	Intermediate Similarity	NPD6675	Approved
0.7547	Intermediate Similarity	NPD6402	Approved
0.7547	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD6009	Approved
0.75	Intermediate Similarity	NPD6013	Approved
0.75	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD6014	Approved
0.7477	Intermediate Similarity	NPD5701	Approved
0.7474	Intermediate Similarity	NPD4788	Approved
0.7473	Intermediate Similarity	NPD6117	Approved
0.7451	Intermediate Similarity	NPD4697	Phase 3
0.7431	Intermediate Similarity	NPD6883	Approved
0.7431	Intermediate Similarity	NPD7290	Approved
0.7431	Intermediate Similarity	NPD4634	Approved
0.7431	Intermediate Similarity	NPD7102	Approved
0.7426	Intermediate Similarity	NPD7748	Approved
0.7423	Intermediate Similarity	NPD3618	Phase 1
0.7407	Intermediate Similarity	NPD7320	Approved
0.7404	Intermediate Similarity	NPD5286	Approved
0.7404	Intermediate Similarity	NPD4696	Approved
0.7404	Intermediate Similarity	NPD5285	Approved
0.7391	Intermediate Similarity	NPD6116	Phase 1
0.7383	Intermediate Similarity	NPD6008	Approved
0.7379	Intermediate Similarity	NPD4755	Approved
0.7364	Intermediate Similarity	NPD6649	Approved
0.7364	Intermediate Similarity	NPD8130	Phase 1
0.7364	Intermediate Similarity	NPD6617	Approved
0.7364	Intermediate Similarity	NPD6650	Approved
0.7364	Intermediate Similarity	NPD6869	Approved
0.7364	Intermediate Similarity	NPD6847	Approved
0.735	Intermediate Similarity	NPD7492	Approved
0.7339	Intermediate Similarity	NPD6373	Approved
0.7339	Intermediate Similarity	NPD6372	Approved
0.7333	Intermediate Similarity	NPD5223	Approved
0.7327	Intermediate Similarity	NPD6399	Phase 3
0.7311	Intermediate Similarity	NPD7736	Approved
0.7304	Intermediate Similarity	NPD6054	Approved
0.7297	Intermediate Similarity	NPD6882	Approved
0.7297	Intermediate Similarity	NPD8297	Approved
0.7288	Intermediate Similarity	NPD6616	Approved
0.7264	Intermediate Similarity	NPD5225	Approved
0.7264	Intermediate Similarity	NPD5226	Approved
0.7264	Intermediate Similarity	NPD5224	Approved
0.7264	Intermediate Similarity	NPD4633	Approved
0.7264	Intermediate Similarity	NPD5211	Phase 2
0.7253	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6016	Approved
0.7241	Intermediate Similarity	NPD6015	Approved
0.7241	Intermediate Similarity	NPD5983	Phase 2
0.7238	Intermediate Similarity	NPD4700	Approved
0.7227	Intermediate Similarity	NPD7078	Approved
0.7216	Intermediate Similarity	NPD4786	Approved
0.7212	Intermediate Similarity	NPD7902	Approved
0.7207	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5175	Approved
0.7196	Intermediate Similarity	NPD5174	Approved
0.7188	Intermediate Similarity	NPD3667	Approved
0.7179	Intermediate Similarity	NPD6370	Approved
0.7179	Intermediate Similarity	NPD5988	Approved
0.7157	Intermediate Similarity	NPD4202	Approved
0.7155	Intermediate Similarity	NPD6059	Approved
0.7143	Intermediate Similarity	NPD5696	Approved
0.713	Intermediate Similarity	NPD5141	Approved
0.7119	Intermediate Similarity	NPD7604	Phase 2
0.7105	Intermediate Similarity	NPD6274	Approved
0.7105	Intermediate Similarity	NPD6868	Approved
0.7103	Intermediate Similarity	NPD7632	Discontinued
0.7083	Intermediate Similarity	NPD8293	Discontinued
0.7071	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6083	Phase 2
0.7048	Intermediate Similarity	NPD6084	Phase 2
0.7043	Intermediate Similarity	NPD7115	Discovery
0.7043	Intermediate Similarity	NPD6317	Approved
0.7041	Intermediate Similarity	NPD3133	Approved
0.7041	Intermediate Similarity	NPD3666	Approved
0.7041	Intermediate Similarity	NPD3665	Phase 1
0.7037	Intermediate Similarity	NPD4754	Approved
0.7033	Intermediate Similarity	NPD6081	Approved
0.7033	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5210	Approved
0.7019	Intermediate Similarity	NPD4629	Approved
0.7	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3573	Approved
0.7	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6336	Discontinued
0.6983	Remote Similarity	NPD6313	Approved
0.6983	Remote Similarity	NPD6314	Approved
0.6983	Remote Similarity	NPD6335	Approved
0.6975	Remote Similarity	NPD8328	Phase 3
0.6967	Remote Similarity	NPD7319	Approved
0.6937	Remote Similarity	NPD5168	Approved
0.6937	Remote Similarity	NPD4730	Approved
0.6937	Remote Similarity	NPD5128	Approved
0.6937	Remote Similarity	NPD4729	Approved
0.6931	Remote Similarity	NPD6672	Approved
0.6931	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5737	Approved
0.693	Remote Similarity	NPD8133	Approved
0.6923	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7101	Approved
0.6923	Remote Similarity	NPD7900	Approved
0.6923	Remote Similarity	NPD7100	Approved
0.6909	Remote Similarity	NPD4767	Approved
0.6909	Remote Similarity	NPD4768	Approved
0.69	Remote Similarity	NPD7334	Approved
0.69	Remote Similarity	NPD7521	Approved
0.69	Remote Similarity	NPD6409	Approved
0.69	Remote Similarity	NPD6684	Approved
0.69	Remote Similarity	NPD5330	Approved
0.69	Remote Similarity	NPD7146	Approved
0.6893	Remote Similarity	NPD6411	Approved
0.6863	Remote Similarity	NPD4753	Phase 2
0.686	Remote Similarity	NPD7507	Approved
0.6857	Remote Similarity	NPD5695	Phase 3
0.6854	Remote Similarity	NPD4224	Phase 2
0.6822	Remote Similarity	NPD4225	Approved
0.6814	Remote Similarity	NPD5251	Approved
0.6814	Remote Similarity	NPD5247	Approved
0.6814	Remote Similarity	NPD5135	Approved
0.6814	Remote Similarity	NPD5248	Approved
0.6814	Remote Similarity	NPD5249	Phase 3
0.6814	Remote Similarity	NPD5250	Approved
0.6814	Remote Similarity	NPD5169	Approved
0.6814	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7525	Registered
0.6765	Remote Similarity	NPD6903	Approved
0.6754	Remote Similarity	NPD5217	Approved
0.6754	Remote Similarity	NPD5216	Approved
0.6754	Remote Similarity	NPD5127	Approved
0.6754	Remote Similarity	NPD5215	Approved
0.6752	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6033	Approved
0.6733	Remote Similarity	NPD5279	Phase 3
0.6726	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.67	Remote Similarity	NPD3668	Phase 3
0.6699	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6101	Approved
0.6698	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD6334	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD6333	Approved
0.6667	Remote Similarity	NPD6909	Approved
0.6637	Remote Similarity	NPD6686	Approved
0.6636	Remote Similarity	NPD7614	Phase 1
0.6632	Remote Similarity	NPD3702	Approved
0.663	Remote Similarity	NPD3698	Phase 2
0.6581	Remote Similarity	NPD5167	Approved
0.6579	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5281	Approved
0.6571	Remote Similarity	NPD5284	Approved
0.6571	Remote Similarity	NPD7637	Suspended
0.6559	Remote Similarity	NPD4244	Approved
0.6559	Remote Similarity	NPD4789	Approved
0.6559	Remote Similarity	NPD4245	Approved
0.6556	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6904	Approved
0.6538	Remote Similarity	NPD6673	Approved
0.6538	Remote Similarity	NPD6080	Approved
0.6535	Remote Similarity	NPD4197	Approved
0.6529	Remote Similarity	NPD6921	Approved
0.6522	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5360	Phase 3
0.65	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5777	Approved
0.6481	Remote Similarity	NPD7732	Phase 3
0.6471	Remote Similarity	NPD5329	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data