NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.18
Volume:	248.481
LogP:	3.025
LogD:	3.284
LogS:	-3.742
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.672
Synthetic Accessibility Score:	5.258
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.539
MDCK Permeability:	1.444385816284921e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.649
30% Bioavailability (F30%):	0.933

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.312
Plasma Protein Binding (PPB):	91.51847076416016%
Volume Distribution (VD):	0.994
Pgp-substrate:	6.132633686065674%

ADMET: Metabolism

CYP1A2-inhibitor:	0.424
CYP1A2-substrate:	0.478
CYP2C19-inhibitor:	0.085
CYP2C19-substrate:	0.846
CYP2C9-inhibitor:	0.067
CYP2C9-substrate:	0.106
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.253
CYP3A4-inhibitor:	0.678
CYP3A4-substrate:	0.421

ADMET: Excretion

Clearance (CL):	9.38
Half-life (T1/2):	0.453

ADMET: Toxicity

hERG Blockers:	0.101
Human Hepatotoxicity (H-HT):	0.34
Drug-inuced Liver Injury (DILI):	0.219
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.174
Maximum Recommended Daily Dose:	0.057
Skin Sensitization:	0.933
Carcinogencity:	0.896
Eye Corrosion:	0.979
Eye Irritation:	0.971
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC162309

Natural Product ID:	NPC162309
*Common Name:**	Subergorgiol
IUPAC Name:	[(3S,3aR,5aR,8S,8aS)-3,5a,8-trimethyl-2,3,3a,4,5,8-hexahydro-1H-cyclopenta[h]pentalen-7-yl]methanol
Synonyms:	Subergorgiol
Standard InCHIKey:	GJNXTRPTZOVADS-PWRGDLIESA-N
Standard InCHI:	InChI=1S/C15H24O/c1-10-4-7-15-11(2)12(9-16)8-14(15,3)6-5-13(10)15/h8,10-11,13,16H,4-7,9H2,1-3H3/t10-,11+,13+,14+,15+/m0/s1
SMILES:	C[C@H]1CC[C@@]23[C@H](C)C(=C[C@@]3(C)CC[C@H]12)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL526710
PubChem CID:	636436
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002004] Triquinane sesquiterpenoids [CHEMONTID:0003582] Angular triquinanes

*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
NPO11745	Subergorgia suberosa	Species	Subergorgiidae	Eukaryota	n.a.	Taiwanese gorgonian coral	n.a.	PMID[12088433]
NPO11745	Subergorgia suberosa	Species	Subergorgiidae	Eukaryota	n.a.	Taiwanese Gorgonian coral	n.a.	PMID[12141868]
NPO11745	Subergorgia suberosa	Species	Subergorgiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124781]
NPO11745	Subergorgia suberosa	Species	Subergorgiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18290631]
NPO11745	Subergorgia suberosa	Species	Subergorgiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[496447]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[496447]

☑ 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 NPC162309 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	166
0.1-0.2	2036
0.2-0.3	14487
0.3-0.4	13137
0.4-0.5	7988
0.5-0.6	4002
0.6-0.7	771
0.7-0.8	95
0.8-0.85	8
0.85-0.9	6
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8923	High Similarity	NPC477791
0.8636	High Similarity	NPC136813
0.8615	High Similarity	NPC19569
0.8571	High Similarity	NPC234264
0.8571	High Similarity	NPC47840
0.8551	High Similarity	NPC234527
0.8551	High Similarity	NPC14352
0.8529	High Similarity	NPC254845
0.8507	High Similarity	NPC167527
0.8462	Intermediate Similarity	NPC309300
0.8429	Intermediate Similarity	NPC309178
0.831	Intermediate Similarity	NPC313185
0.8308	Intermediate Similarity	NPC124112
0.8194	Intermediate Similarity	NPC310643
0.8182	Intermediate Similarity	NPC475704
0.8154	Intermediate Similarity	NPC210346
0.8143	Intermediate Similarity	NPC471662
0.806	Intermediate Similarity	NPC238352
0.806	Intermediate Similarity	NPC477009
0.803	Intermediate Similarity	NPC211291
0.803	Intermediate Similarity	NPC133368
0.7969	Intermediate Similarity	NPC10017
0.7941	Intermediate Similarity	NPC135650
0.7917	Intermediate Similarity	NPC471659
0.791	Intermediate Similarity	NPC110241
0.7879	Intermediate Similarity	NPC147524
0.7857	Intermediate Similarity	NPC217570
0.7857	Intermediate Similarity	NPC90115
0.7846	Intermediate Similarity	NPC309825
0.7846	Intermediate Similarity	NPC5698
0.7826	Intermediate Similarity	NPC74885
0.7826	Intermediate Similarity	NPC308522
0.7794	Intermediate Similarity	NPC187619
0.7778	Intermediate Similarity	NPC298299
0.7778	Intermediate Similarity	NPC474743
0.7761	Intermediate Similarity	NPC474155
0.7761	Intermediate Similarity	NPC473759
0.7761	Intermediate Similarity	NPC474480
0.7746	Intermediate Similarity	NPC133873
0.7727	Intermediate Similarity	NPC471081
0.7727	Intermediate Similarity	NPC323153
0.7714	Intermediate Similarity	NPC224532
0.7714	Intermediate Similarity	NPC160209
0.7703	Intermediate Similarity	NPC247325
0.7703	Intermediate Similarity	NPC126969
0.7703	Intermediate Similarity	NPC471658
0.7703	Intermediate Similarity	NPC244488
0.7647	Intermediate Similarity	NPC107540
0.7612	Intermediate Similarity	NPC15152
0.7571	Intermediate Similarity	NPC68703
0.7571	Intermediate Similarity	NPC69649
0.7571	Intermediate Similarity	NPC171225
0.7568	Intermediate Similarity	NPC23231
0.7568	Intermediate Similarity	NPC60818
0.7564	Intermediate Similarity	NPC472465
0.7538	Intermediate Similarity	NPC278550
0.75	Intermediate Similarity	NPC130209
0.75	Intermediate Similarity	NPC148216
0.75	Intermediate Similarity	NPC148163
0.75	Intermediate Similarity	NPC279200
0.7465	Intermediate Similarity	NPC96484
0.7463	Intermediate Similarity	NPC135648
0.7463	Intermediate Similarity	NPC66020
0.7463	Intermediate Similarity	NPC252809
0.7429	Intermediate Similarity	NPC272125
0.7424	Intermediate Similarity	NPC475830
0.7403	Intermediate Similarity	NPC84694
0.7403	Intermediate Similarity	NPC30986
0.7403	Intermediate Similarity	NPC109546
0.7403	Intermediate Similarity	NPC81306
0.7403	Intermediate Similarity	NPC209430
0.7403	Intermediate Similarity	NPC28862
0.7403	Intermediate Similarity	NPC47982
0.7403	Intermediate Similarity	NPC143182
0.7397	Intermediate Similarity	NPC471660
0.7391	Intermediate Similarity	NPC300593
0.7361	Intermediate Similarity	NPC474248
0.7361	Intermediate Similarity	NPC471560
0.7353	Intermediate Similarity	NPC225342
0.7353	Intermediate Similarity	NPC274704
0.7349	Intermediate Similarity	NPC232747
0.7324	Intermediate Similarity	NPC114651
0.7324	Intermediate Similarity	NPC472255
0.7324	Intermediate Similarity	NPC472253
0.7313	Intermediate Similarity	NPC122239
0.7308	Intermediate Similarity	NPC234193
0.7297	Intermediate Similarity	NPC474140
0.7273	Intermediate Similarity	NPC470944
0.7273	Intermediate Similarity	NPC474216
0.726	Intermediate Similarity	NPC34834
0.725	Intermediate Similarity	NPC65350
0.725	Intermediate Similarity	NPC472473
0.7246	Intermediate Similarity	NPC473508
0.7237	Intermediate Similarity	NPC476317
0.7222	Intermediate Similarity	NPC471238
0.7215	Intermediate Similarity	NPC264245
0.7215	Intermediate Similarity	NPC472471
0.7215	Intermediate Similarity	NPC23852
0.7215	Intermediate Similarity	NPC209620
0.7206	Intermediate Similarity	NPC240506
0.7206	Intermediate Similarity	NPC99487
0.72	Intermediate Similarity	NPC329090
0.72	Intermediate Similarity	NPC469534
0.72	Intermediate Similarity	NPC27395
0.72	Intermediate Similarity	NPC469593
0.72	Intermediate Similarity	NPC469533
0.7183	Intermediate Similarity	NPC202017
0.7183	Intermediate Similarity	NPC267027
0.7164	Intermediate Similarity	NPC155025
0.7162	Intermediate Similarity	NPC477792
0.7162	Intermediate Similarity	NPC41886
0.7162	Intermediate Similarity	NPC469343
0.7143	Intermediate Similarity	NPC287744
0.7143	Intermediate Similarity	NPC323424
0.7143	Intermediate Similarity	NPC219940
0.7143	Intermediate Similarity	NPC96793
0.7143	Intermediate Similarity	NPC140233
0.7143	Intermediate Similarity	NPC225415
0.7125	Intermediate Similarity	NPC49964
0.7125	Intermediate Similarity	NPC50964
0.7125	Intermediate Similarity	NPC87489
0.7125	Intermediate Similarity	NPC189972
0.7125	Intermediate Similarity	NPC296701
0.7125	Intermediate Similarity	NPC202389
0.7125	Intermediate Similarity	NPC101462
0.7125	Intermediate Similarity	NPC218616
0.7123	Intermediate Similarity	NPC167272
0.7123	Intermediate Similarity	NPC473893
0.7123	Intermediate Similarity	NPC269877
0.7121	Intermediate Similarity	NPC48891
0.7105	Intermediate Similarity	NPC288035
0.7105	Intermediate Similarity	NPC471723
0.7105	Intermediate Similarity	NPC319090
0.7105	Intermediate Similarity	NPC162742
0.7105	Intermediate Similarity	NPC141071
0.7105	Intermediate Similarity	NPC28657
0.7105	Intermediate Similarity	NPC328104
0.7105	Intermediate Similarity	NPC136188
0.7105	Intermediate Similarity	NPC230301
0.7105	Intermediate Similarity	NPC471468
0.7105	Intermediate Similarity	NPC285893
0.7105	Intermediate Similarity	NPC22105
0.7105	Intermediate Similarity	NPC304309
0.7105	Intermediate Similarity	NPC134847
0.7105	Intermediate Similarity	NPC257347
0.7101	Intermediate Similarity	NPC63111
0.7089	Intermediate Similarity	NPC324772
0.7089	Intermediate Similarity	NPC209944
0.7089	Intermediate Similarity	NPC164840
0.7089	Intermediate Similarity	NPC241290
0.7077	Intermediate Similarity	NPC286752
0.7067	Intermediate Similarity	NPC329763
0.7059	Intermediate Similarity	NPC469321
0.7059	Intermediate Similarity	NPC475931
0.7051	Intermediate Similarity	NPC473943
0.7051	Intermediate Similarity	NPC477514
0.7042	Intermediate Similarity	NPC61503
0.7042	Intermediate Similarity	NPC300442
0.7037	Intermediate Similarity	NPC317458
0.7037	Intermediate Similarity	NPC474634
0.7037	Intermediate Similarity	NPC475789
0.7037	Intermediate Similarity	NPC470384
0.7027	Intermediate Similarity	NPC49422
0.7027	Intermediate Similarity	NPC471781
0.7027	Intermediate Similarity	NPC9161
0.7027	Intermediate Similarity	NPC470041
0.7015	Intermediate Similarity	NPC11130
0.7013	Intermediate Similarity	NPC321016
0.7013	Intermediate Similarity	NPC470362
0.7013	Intermediate Similarity	NPC315261
0.7013	Intermediate Similarity	NPC134330
0.7013	Intermediate Similarity	NPC321381
0.7013	Intermediate Similarity	NPC189883
0.7013	Intermediate Similarity	NPC469646
0.7013	Intermediate Similarity	NPC240604
0.7013	Intermediate Similarity	NPC472472
0.7013	Intermediate Similarity	NPC46160
0.7013	Intermediate Similarity	NPC113733
0.7013	Intermediate Similarity	NPC300324
0.7013	Intermediate Similarity	NPC129165
0.7013	Intermediate Similarity	NPC202642
0.7013	Intermediate Similarity	NPC107059
0.7013	Intermediate Similarity	NPC237460
0.7	Intermediate Similarity	NPC7505
0.7	Intermediate Similarity	NPC474731
0.7	Intermediate Similarity	NPC81615
0.7	Intermediate Similarity	NPC47761
0.7	Intermediate Similarity	NPC320525
0.7	Intermediate Similarity	NPC82986
0.7	Intermediate Similarity	NPC471661
0.7	Intermediate Similarity	NPC474759
0.7	Intermediate Similarity	NPC474752
0.7	Intermediate Similarity	NPC474683
0.6984	Remote Similarity	NPC26960
0.6984	Remote Similarity	NPC182102
0.6974	Remote Similarity	NPC206875
0.6974	Remote Similarity	NPC201048
0.6974	Remote Similarity	NPC476366
0.6974	Remote Similarity	NPC306727
0.6962	Remote Similarity	NPC7232

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 NPC162309 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	2697
0.2-0.3	4368
0.3-0.4	1406
0.4-0.5	338
0.5-0.6	129
0.6-0.7	50
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.75	Intermediate Similarity	NPD342	Phase 1
0.72	Intermediate Similarity	NPD6924	Approved
0.72	Intermediate Similarity	NPD6926	Approved
0.7179	Intermediate Similarity	NPD6929	Approved
0.7123	Intermediate Similarity	NPD6922	Approved
0.7123	Intermediate Similarity	NPD6923	Approved
0.7105	Intermediate Similarity	NPD6942	Approved
0.7105	Intermediate Similarity	NPD7339	Approved
0.7089	Intermediate Similarity	NPD6930	Phase 2
0.7089	Intermediate Similarity	NPD6931	Approved
0.7051	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7143	Approved
0.7027	Intermediate Similarity	NPD7144	Approved
0.7013	Intermediate Similarity	NPD6933	Approved
0.7	Intermediate Similarity	NPD4790	Discontinued
0.6933	Remote Similarity	NPD7150	Approved
0.6933	Remote Similarity	NPD7151	Approved
0.6933	Remote Similarity	NPD7152	Approved
0.6923	Remote Similarity	NPD6925	Approved
0.6923	Remote Similarity	NPD5776	Phase 2
0.6875	Remote Similarity	NPD7514	Phase 3
0.6875	Remote Similarity	NPD7332	Phase 2
0.6857	Remote Similarity	NPD368	Approved
0.6835	Remote Similarity	NPD7145	Approved
0.6835	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5332	Approved
0.6829	Remote Similarity	NPD5362	Discontinued
0.6829	Remote Similarity	NPD6695	Phase 3
0.6829	Remote Similarity	NPD5331	Approved
0.6795	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6902	Approved
0.6747	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4243	Approved
0.6706	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD7509	Discontinued
0.6667	Remote Similarity	NPD7525	Registered
0.6618	Remote Similarity	NPD4219	Approved
0.6585	Remote Similarity	NPD6898	Phase 1
0.6538	Remote Similarity	NPD4784	Approved
0.6538	Remote Similarity	NPD4785	Approved
0.6512	Remote Similarity	NPD7750	Discontinued
0.6512	Remote Similarity	NPD7524	Approved
0.65	Remote Similarity	NPD6932	Approved
0.6471	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD4190	Phase 3
0.6456	Remote Similarity	NPD8264	Approved
0.6456	Remote Similarity	NPD5275	Approved
0.6353	Remote Similarity	NPD4786	Approved
0.6341	Remote Similarity	NPD6683	Phase 2
0.631	Remote Similarity	NPD3667	Approved
0.6265	Remote Similarity	NPD4821	Approved
0.6265	Remote Similarity	NPD4819	Approved
0.6265	Remote Similarity	NPD4822	Approved
0.6265	Remote Similarity	NPD4820	Approved
0.6222	Remote Similarity	NPD7087	Discontinued
0.622	Remote Similarity	NPD4271	Approved
0.622	Remote Similarity	NPD4268	Approved
0.6207	Remote Similarity	NPD5279	Phase 3
0.6163	Remote Similarity	NPD3133	Approved
0.6163	Remote Similarity	NPD3665	Phase 1
0.6163	Remote Similarity	NPD3666	Approved
0.6145	Remote Similarity	NPD4195	Approved
0.6118	Remote Similarity	NPD4269	Approved
0.6118	Remote Similarity	NPD4270	Approved
0.6094	Remote Similarity	NPD4265	Approved
0.6071	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4748	Discontinued
0.6047	Remote Similarity	NPD7154	Phase 3
0.6044	Remote Similarity	NPD7637	Suspended
0.6023	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD4753	Phase 2
0.6	Remote Similarity	NPD5328	Approved
0.5976	Remote Similarity	NPD1346	Approved
0.5952	Remote Similarity	NPD7645	Phase 2
0.5934	Remote Similarity	NPD7136	Phase 2
0.5934	Remote Similarity	NPD5785	Approved
0.593	Remote Similarity	NPD4221	Approved
0.593	Remote Similarity	NPD4223	Phase 3
0.5909	Remote Similarity	NPD5363	Approved
0.5909	Remote Similarity	NPD1696	Phase 3
0.5882	Remote Similarity	NPD4252	Approved
0.587	Remote Similarity	NPD6079	Approved
0.5843	Remote Similarity	NPD4623	Approved
0.5843	Remote Similarity	NPD5786	Approved
0.5843	Remote Similarity	NPD4249	Approved
0.5843	Remote Similarity	NPD4519	Discontinued
0.5814	Remote Similarity	NPD857	Phase 3
0.5806	Remote Similarity	NPD4202	Approved
0.5802	Remote Similarity	NPD4732	Discontinued
0.5795	Remote Similarity	NPD4197	Approved
0.5778	Remote Similarity	NPD4250	Approved
0.5778	Remote Similarity	NPD4251	Approved
0.5773	Remote Similarity	NPD7639	Approved
0.5773	Remote Similarity	NPD7640	Approved
0.573	Remote Similarity	NPD5329	Approved
0.5698	Remote Similarity	NPD5368	Approved
0.5684	Remote Similarity	NPD5210	Approved
0.5684	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD4629	Approved
0.5682	Remote Similarity	NPD4788	Approved
0.567	Remote Similarity	NPD7638	Approved
0.5667	Remote Similarity	NPD4694	Approved
0.5667	Remote Similarity	NPD4689	Approved
0.5667	Remote Similarity	NPD4693	Phase 3
0.5667	Remote Similarity	NPD5205	Approved
0.5667	Remote Similarity	NPD4690	Approved
0.5667	Remote Similarity	NPD5280	Approved
0.5667	Remote Similarity	NPD4138	Approved
0.5667	Remote Similarity	NPD5690	Phase 2
0.5667	Remote Similarity	NPD4688	Approved
0.5657	Remote Similarity	NPD5211	Phase 2
0.5652	Remote Similarity	NPD6051	Approved
0.5638	Remote Similarity	NPD6399	Phase 3
0.5632	Remote Similarity	NPD5369	Approved
0.5625	Remote Similarity	NPD5222	Approved
0.5625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4697	Phase 3
0.5625	Remote Similarity	NPD5221	Approved
0.5618	Remote Similarity	NPD3668	Phase 3

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