NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.19
Volume:	283.357
LogP:	2.718
LogD:	2.928
LogS:	-3.216
# Rotatable Bonds:	1
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.742
Synthetic Accessibility Score:	4.72
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.588
MDCK Permeability:	1.612688720342703e-05
Pgp-inhibitor:	0.277
Pgp-substrate:	0.97
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.724
30% Bioavailability (F30%):	0.073

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.796
Plasma Protein Binding (PPB):	36.47605895996094%
Volume Distribution (VD):	1.681
Pgp-substrate:	49.11314392089844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.822
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.208
CYP3A4-inhibitor:	0.139
CYP3A4-substrate:	0.389

ADMET: Excretion

Clearance (CL):	13.03
Half-life (T1/2):	0.359

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.299
Drug-inuced Liver Injury (DILI):	0.36
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.86
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.163
Carcinogencity:	0.92
Eye Corrosion:	0.153
Eye Irritation:	0.503
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC122945

Natural Product ID:	NPC122945
*Common Name:**	Armatin C
IUPAC Name:	(1S,2S,3aR,7S,9S,9aS,9bR)-2-methoxy-1,9,9a-trimethyl-2,3a,4,5,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran-7-ol
Synonyms:	Armatin C
Standard InCHIKey:	RVIFTQUMZYSBBG-AOEFDIKDSA-N
Standard InCHI:	InChI=1S/C16H26O3/c1-9-7-12(17)8-11-5-6-13-14(16(9,11)3)10(2)15(18-4)19-13/h8-10,12-15,17H,5-7H2,1-4H3/t9-,10-,12-,13+,14-,15-,16+/m0/s1
SMILES:	CO[C@H]1O[C@H]2[C@H]([C@@H]1C)[C@]1(C)[C@@H](C)C[C@@H](C=C1CC2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456746
PubChem CID:	11161444
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO21076	Nephthea armata	Species	Nephtheidae	Eukaryota	n.a.	Taiwan	n.a.	PMID[15387641]
NPO21076	Nephthea armata	Species	Nephtheidae	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
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	50000.0	nM	PMID[573726]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[573726]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	50000.0	nM	PMID[573726]

☑ 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 NPC122945 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	147
0.1-0.2	1291
0.2-0.3	5392
0.3-0.4	14883
0.4-0.5	8794
0.5-0.6	7013
0.6-0.7	4371
0.7-0.8	768
0.8-0.85	29
0.85-0.9	6
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC109938
0.9737	High Similarity	NPC206062
0.9048	High Similarity	NPC470817
0.8929	High Similarity	NPC470819
0.8675	High Similarity	NPC119001
0.8625	High Similarity	NPC17550
0.8554	High Similarity	NPC46320
0.8488	Intermediate Similarity	NPC477917
0.8427	Intermediate Similarity	NPC100892
0.8427	Intermediate Similarity	NPC477970
0.8391	Intermediate Similarity	NPC469403
0.8353	Intermediate Similarity	NPC173917
0.8333	Intermediate Similarity	NPC319238
0.8315	Intermediate Similarity	NPC189513
0.8222	Intermediate Similarity	NPC135224
0.8222	Intermediate Similarity	NPC477969
0.8095	Intermediate Similarity	NPC155521
0.809	Intermediate Similarity	NPC472811
0.809	Intermediate Similarity	NPC302584
0.8077	Intermediate Similarity	NPC34834
0.8068	Intermediate Similarity	NPC473058
0.8068	Intermediate Similarity	NPC470734
0.8043	Intermediate Similarity	NPC98112
0.8043	Intermediate Similarity	NPC240372
0.8023	Intermediate Similarity	NPC473251
0.8023	Intermediate Similarity	NPC300985
0.8023	Intermediate Similarity	NPC52628
0.8023	Intermediate Similarity	NPC42586
0.8	Intermediate Similarity	NPC472812
0.7978	Intermediate Similarity	NPC159876
0.7975	Intermediate Similarity	NPC23954
0.7957	Intermediate Similarity	NPC473154
0.7955	Intermediate Similarity	NPC472809
0.7955	Intermediate Similarity	NPC472810
0.7935	Intermediate Similarity	NPC90583
0.7931	Intermediate Similarity	NPC323209
0.7927	Intermediate Similarity	NPC477427
0.7927	Intermediate Similarity	NPC91594
0.7927	Intermediate Similarity	NPC477426
0.7927	Intermediate Similarity	NPC474826
0.7927	Intermediate Similarity	NPC477425
0.7895	Intermediate Similarity	NPC471363
0.7895	Intermediate Similarity	NPC300399
0.7895	Intermediate Similarity	NPC238397
0.7895	Intermediate Similarity	NPC471482
0.7872	Intermediate Similarity	NPC20113
0.7872	Intermediate Similarity	NPC228251
0.7872	Intermediate Similarity	NPC161527
0.7872	Intermediate Similarity	NPC64348
0.7872	Intermediate Similarity	NPC477972
0.7872	Intermediate Similarity	NPC219285
0.7872	Intermediate Similarity	NPC477968
0.7872	Intermediate Similarity	NPC477971
0.7857	Intermediate Similarity	NPC96362
0.7848	Intermediate Similarity	NPC92801
0.7831	Intermediate Similarity	NPC476314
0.7826	Intermediate Similarity	NPC13924
0.7826	Intermediate Similarity	NPC472441
0.7821	Intermediate Similarity	NPC96484
0.7821	Intermediate Similarity	NPC471238
0.7812	Intermediate Similarity	NPC471886
0.7812	Intermediate Similarity	NPC7613
0.7812	Intermediate Similarity	NPC127933
0.7812	Intermediate Similarity	NPC471887
0.7812	Intermediate Similarity	NPC471888
0.7812	Intermediate Similarity	NPC134270
0.7812	Intermediate Similarity	NPC471885
0.7812	Intermediate Similarity	NPC475889
0.7812	Intermediate Similarity	NPC471450
0.7812	Intermediate Similarity	NPC7644
0.7805	Intermediate Similarity	NPC253190
0.7805	Intermediate Similarity	NPC265588
0.7778	Intermediate Similarity	NPC471432
0.7778	Intermediate Similarity	NPC201048
0.7778	Intermediate Similarity	NPC476366
0.7778	Intermediate Similarity	NPC471433
0.7778	Intermediate Similarity	NPC306727
0.7766	Intermediate Similarity	NPC5358
0.7766	Intermediate Similarity	NPC216260
0.7765	Intermediate Similarity	NPC476646
0.775	Intermediate Similarity	NPC164022
0.775	Intermediate Similarity	NPC471272
0.775	Intermediate Similarity	NPC477792
0.7738	Intermediate Similarity	NPC209430
0.7738	Intermediate Similarity	NPC30986
0.7738	Intermediate Similarity	NPC242767
0.7732	Intermediate Similarity	NPC81567
0.7732	Intermediate Similarity	NPC264867
0.7732	Intermediate Similarity	NPC470321
0.7732	Intermediate Similarity	NPC75608
0.7732	Intermediate Similarity	NPC473207
0.7732	Intermediate Similarity	NPC201880
0.7727	Intermediate Similarity	NPC329692
0.7722	Intermediate Similarity	NPC471560
0.7722	Intermediate Similarity	NPC474248
0.7717	Intermediate Similarity	NPC470255
0.7717	Intermediate Similarity	NPC305160
0.7717	Intermediate Similarity	NPC104925
0.7717	Intermediate Similarity	NPC477927
0.7717	Intermediate Similarity	NPC72817
0.7717	Intermediate Similarity	NPC298973
0.7711	Intermediate Similarity	NPC470711
0.7711	Intermediate Similarity	NPC470758
0.7711	Intermediate Similarity	NPC283619
0.7708	Intermediate Similarity	NPC471889
0.7708	Intermediate Similarity	NPC37207
0.7701	Intermediate Similarity	NPC102048
0.7701	Intermediate Similarity	NPC474047
0.7692	Intermediate Similarity	NPC69649
0.7692	Intermediate Similarity	NPC179517
0.7692	Intermediate Similarity	NPC68703
0.7692	Intermediate Similarity	NPC94127
0.7692	Intermediate Similarity	NPC165904
0.7684	Intermediate Similarity	NPC324841
0.7684	Intermediate Similarity	NPC469942
0.7684	Intermediate Similarity	NPC324598
0.7683	Intermediate Similarity	NPC291503
0.7683	Intermediate Similarity	NPC32832
0.7677	Intermediate Similarity	NPC470024
0.7674	Intermediate Similarity	NPC256112
0.7674	Intermediate Similarity	NPC470049
0.7674	Intermediate Similarity	NPC87489
0.7674	Intermediate Similarity	NPC202389
0.7667	Intermediate Similarity	NPC293044
0.7654	Intermediate Similarity	NPC220939
0.7654	Intermediate Similarity	NPC474140
0.7654	Intermediate Similarity	NPC265485
0.7653	Intermediate Similarity	NPC252296
0.7653	Intermediate Similarity	NPC172867
0.7647	Intermediate Similarity	NPC295131
0.7647	Intermediate Similarity	NPC281880
0.764	Intermediate Similarity	NPC476948
0.764	Intermediate Similarity	NPC166857
0.7634	Intermediate Similarity	NPC476894
0.7634	Intermediate Similarity	NPC472189
0.7634	Intermediate Similarity	NPC286612
0.7634	Intermediate Similarity	NPC230347
0.7634	Intermediate Similarity	NPC275310
0.7634	Intermediate Similarity	NPC471362
0.7634	Intermediate Similarity	NPC471372
0.7629	Intermediate Similarity	NPC162354
0.7619	Intermediate Similarity	NPC11908
0.7614	Intermediate Similarity	NPC16350
0.7614	Intermediate Similarity	NPC308041
0.7609	Intermediate Similarity	NPC474792
0.7609	Intermediate Similarity	NPC91654
0.7609	Intermediate Similarity	NPC67398
0.7604	Intermediate Similarity	NPC470434
0.7595	Intermediate Similarity	NPC470040
0.759	Intermediate Similarity	NPC247325
0.759	Intermediate Similarity	NPC244488
0.759	Intermediate Similarity	NPC470749
0.7586	Intermediate Similarity	NPC311070
0.7586	Intermediate Similarity	NPC471297
0.7579	Intermediate Similarity	NPC474440
0.7576	Intermediate Similarity	NPC125423
0.7576	Intermediate Similarity	NPC88013
0.7576	Intermediate Similarity	NPC476594
0.7576	Intermediate Similarity	NPC184512
0.7576	Intermediate Similarity	NPC109376
0.7564	Intermediate Similarity	NPC202017
0.7561	Intermediate Similarity	NPC243342
0.7561	Intermediate Similarity	NPC477138
0.7561	Intermediate Similarity	NPC91858
0.7561	Intermediate Similarity	NPC469534
0.7561	Intermediate Similarity	NPC469533
0.7561	Intermediate Similarity	NPC469593
0.7558	Intermediate Similarity	NPC170303
0.7558	Intermediate Similarity	NPC249423
0.7558	Intermediate Similarity	NPC142163
0.7558	Intermediate Similarity	NPC159148
0.7556	Intermediate Similarity	NPC263079
0.7556	Intermediate Similarity	NPC471952
0.7556	Intermediate Similarity	NPC472378
0.7553	Intermediate Similarity	NPC165632
0.7553	Intermediate Similarity	NPC8954
0.7553	Intermediate Similarity	NPC94905
0.7553	Intermediate Similarity	NPC171598
0.7551	Intermediate Similarity	NPC470768
0.7551	Intermediate Similarity	NPC222161
0.7532	Intermediate Similarity	NPC96793
0.7532	Intermediate Similarity	NPC225415
0.7532	Intermediate Similarity	NPC323424
0.7531	Intermediate Similarity	NPC471268
0.7531	Intermediate Similarity	NPC471271
0.7531	Intermediate Similarity	NPC242001
0.7531	Intermediate Similarity	NPC167706
0.7529	Intermediate Similarity	NPC28862
0.7529	Intermediate Similarity	NPC81306
0.7529	Intermediate Similarity	NPC143182
0.7529	Intermediate Similarity	NPC84694
0.7529	Intermediate Similarity	NPC100906
0.7529	Intermediate Similarity	NPC109546
0.7529	Intermediate Similarity	NPC47982
0.7528	Intermediate Similarity	NPC131813
0.7528	Intermediate Similarity	NPC6979
0.7528	Intermediate Similarity	NPC473226
0.7528	Intermediate Similarity	NPC198761
0.7528	Intermediate Similarity	NPC118266
0.7527	Intermediate Similarity	NPC469697

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 NPC122945 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	1619
0.2-0.3	4179
0.3-0.4	2267
0.4-0.5	535
0.5-0.6	259
0.6-0.7	140
0.7-0.8	12
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
0.7326	Intermediate Similarity	NPD7645	Phase 2
0.7262	Intermediate Similarity	NPD8264	Approved
0.7241	Intermediate Similarity	NPD7525	Registered
0.7176	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7339	Approved
0.7059	Intermediate Similarity	NPD6942	Approved
0.7051	Intermediate Similarity	NPD368	Approved
0.7041	Intermediate Similarity	NPD4225	Approved
0.7	Intermediate Similarity	NPD6695	Phase 3
0.6941	Remote Similarity	NPD6926	Approved
0.6941	Remote Similarity	NPD6924	Approved
0.6932	Remote Similarity	NPD6929	Approved
0.6882	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6930	Phase 2
0.6854	Remote Similarity	NPD7509	Discontinued
0.6854	Remote Similarity	NPD6931	Approved
0.6827	Remote Similarity	NPD6686	Approved
0.6818	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7640	Approved
0.68	Remote Similarity	NPD7639	Approved
0.6782	Remote Similarity	NPD6933	Approved
0.6774	Remote Similarity	NPD3618	Phase 1
0.6731	Remote Similarity	NPD6412	Phase 2
0.6705	Remote Similarity	NPD5776	Phase 2
0.6705	Remote Similarity	NPD6925	Approved
0.6703	Remote Similarity	NPD3667	Approved
0.6702	Remote Similarity	NPD7524	Approved
0.6702	Remote Similarity	NPD7750	Discontinued
0.67	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD7514	Phase 3
0.6667	Remote Similarity	NPD7332	Phase 2
0.6667	Remote Similarity	NPD6922	Approved
0.6667	Remote Similarity	NPD6923	Approved
0.6629	Remote Similarity	NPD7145	Approved
0.6593	Remote Similarity	NPD6902	Approved
0.6588	Remote Similarity	NPD7144	Approved
0.6588	Remote Similarity	NPD7143	Approved
0.6577	Remote Similarity	NPD7328	Approved
0.6577	Remote Similarity	NPD7327	Approved
0.6562	Remote Similarity	NPD5328	Approved
0.6559	Remote Similarity	NPD3666	Approved
0.6559	Remote Similarity	NPD4786	Approved
0.6559	Remote Similarity	NPD3665	Phase 1
0.6559	Remote Similarity	NPD3133	Approved
0.6549	Remote Similarity	NPD7503	Approved
0.6531	Remote Similarity	NPD6399	Phase 3
0.6531	Remote Similarity	NPD4202	Approved
0.6518	Remote Similarity	NPD7516	Approved
0.6512	Remote Similarity	NPD4243	Approved
0.6512	Remote Similarity	NPD7150	Approved
0.6512	Remote Similarity	NPD7152	Approved
0.6512	Remote Similarity	NPD7151	Approved
0.6494	Remote Similarity	NPD342	Phase 1
0.6489	Remote Similarity	NPD1694	Approved
0.6489	Remote Similarity	NPD6893	Approved
0.6484	Remote Similarity	NPD4748	Discontinued
0.6465	Remote Similarity	NPD7748	Approved
0.646	Remote Similarity	NPD8377	Approved
0.646	Remote Similarity	NPD8294	Approved
0.6436	Remote Similarity	NPD7902	Approved
0.6429	Remote Similarity	NPD7515	Phase 2
0.6429	Remote Similarity	NPD6079	Approved
0.6429	Remote Similarity	NPD7637	Suspended
0.6429	Remote Similarity	NPD7087	Discontinued
0.6422	Remote Similarity	NPD6882	Approved
0.6421	Remote Similarity	NPD5279	Phase 3
0.6413	Remote Similarity	NPD6898	Phase 1
0.6404	Remote Similarity	NPD8379	Approved
0.6404	Remote Similarity	NPD8378	Approved
0.6404	Remote Similarity	NPD8296	Approved
0.6404	Remote Similarity	NPD8380	Approved
0.6404	Remote Similarity	NPD8335	Approved
0.6404	Remote Similarity	NPD8033	Approved
0.6392	Remote Similarity	NPD6051	Approved
0.6364	Remote Similarity	NPD5778	Approved
0.6364	Remote Similarity	NPD4785	Approved
0.6364	Remote Similarity	NPD5779	Approved
0.6364	Remote Similarity	NPD4784	Approved
0.6348	Remote Similarity	NPD6370	Approved
0.6346	Remote Similarity	NPD5211	Phase 2
0.6344	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6932	Approved
0.6321	Remote Similarity	NPD7128	Approved
0.6321	Remote Similarity	NPD5739	Approved
0.6321	Remote Similarity	NPD6402	Approved
0.6321	Remote Similarity	NPD6675	Approved
0.6296	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD1145	Discontinued
0.6293	Remote Similarity	NPD6067	Discontinued
0.6292	Remote Similarity	NPD4190	Phase 3
0.6292	Remote Similarity	NPD5275	Approved
0.6275	Remote Similarity	NPD4755	Approved
0.6263	Remote Similarity	NPD6411	Approved
0.6262	Remote Similarity	NPD5697	Approved
0.6262	Remote Similarity	NPD5701	Approved
0.625	Remote Similarity	NPD4519	Discontinued
0.625	Remote Similarity	NPD6409	Approved
0.625	Remote Similarity	NPD5330	Approved
0.625	Remote Similarity	NPD7521	Approved
0.625	Remote Similarity	NPD4623	Approved
0.625	Remote Similarity	NPD6684	Approved
0.625	Remote Similarity	NPD7334	Approved
0.625	Remote Similarity	NPD7146	Approved
0.6226	Remote Similarity	NPD5141	Approved
0.6204	Remote Similarity	NPD7320	Approved
0.6204	Remote Similarity	NPD6899	Approved
0.6204	Remote Similarity	NPD6011	Approved
0.6204	Remote Similarity	NPD6881	Approved
0.6203	Remote Similarity	NPD4219	Approved
0.6196	Remote Similarity	NPD4195	Approved
0.6196	Remote Similarity	NPD6683	Phase 2
0.619	Remote Similarity	NPD7632	Discontinued
0.6186	Remote Similarity	NPD7507	Approved
0.6176	Remote Similarity	NPD5221	Approved
0.6176	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4697	Phase 3
0.6176	Remote Similarity	NPD5222	Approved
0.6174	Remote Similarity	NPD6059	Approved
0.6174	Remote Similarity	NPD6054	Approved
0.6162	Remote Similarity	NPD3168	Discontinued
0.6154	Remote Similarity	NPD4700	Approved
0.6154	Remote Similarity	NPD4696	Approved
0.6154	Remote Similarity	NPD5286	Approved
0.6154	Remote Similarity	NPD5285	Approved
0.6147	Remote Similarity	NPD6373	Approved
0.6147	Remote Similarity	NPD6013	Approved
0.6147	Remote Similarity	NPD6012	Approved
0.6147	Remote Similarity	NPD6372	Approved
0.6147	Remote Similarity	NPD6014	Approved
0.6146	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7900	Approved
0.6139	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD8293	Discontinued
0.6129	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6928	Phase 2
0.6122	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6903	Approved
0.6121	Remote Similarity	NPD6015	Approved
0.6121	Remote Similarity	NPD6016	Approved
0.6117	Remote Similarity	NPD6083	Phase 2
0.6117	Remote Similarity	NPD6084	Phase 2
0.6117	Remote Similarity	NPD5173	Approved
0.61	Remote Similarity	NPD8034	Phase 2
0.61	Remote Similarity	NPD8035	Phase 2
0.6095	Remote Similarity	NPD4159	Approved
0.6095	Remote Similarity	NPD5344	Discontinued
0.6095	Remote Similarity	NPD5223	Approved
0.6091	Remote Similarity	NPD7290	Approved
0.6091	Remote Similarity	NPD7102	Approved
0.6091	Remote Similarity	NPD6883	Approved
0.6087	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7736	Approved
0.6078	Remote Similarity	NPD5695	Phase 3
0.6068	Remote Similarity	NPD5988	Approved
0.6061	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6101	Approved
0.6061	Remote Similarity	NPD4753	Phase 2
0.6058	Remote Similarity	NPD5290	Discontinued
0.6053	Remote Similarity	NPD7115	Discovery
0.6053	Remote Similarity	NPD6009	Approved
0.6042	Remote Similarity	NPD3668	Phase 3
0.6038	Remote Similarity	NPD5224	Approved
0.6038	Remote Similarity	NPD5226	Approved
0.6038	Remote Similarity	NPD4633	Approved
0.6038	Remote Similarity	NPD5225	Approved
0.6036	Remote Similarity	NPD6650	Approved
0.6036	Remote Similarity	NPD6869	Approved
0.6036	Remote Similarity	NPD6847	Approved
0.6036	Remote Similarity	NPD6617	Approved
0.6036	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD8130	Phase 1
0.6036	Remote Similarity	NPD6649	Approved
0.6033	Remote Similarity	NPD7319	Approved
0.6017	Remote Similarity	NPD8328	Phase 3
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4221	Approved
0.6	Remote Similarity	NPD4223	Phase 3
0.6	Remote Similarity	NPD1811	Approved
0.6	Remote Similarity	NPD1810	Approved
0.5983	Remote Similarity	NPD8517	Approved
0.5983	Remote Similarity	NPD8515	Approved
0.5983	Remote Similarity	NPD8513	Phase 3
0.5983	Remote Similarity	NPD8516	Approved
0.5982	Remote Similarity	NPD8297	Approved
0.5981	Remote Similarity	NPD4754	Approved
0.5981	Remote Similarity	NPD5174	Approved
0.5981	Remote Similarity	NPD5175	Approved
0.5979	Remote Similarity	NPD1696	Phase 3
0.5979	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD7492	Approved
0.596	Remote Similarity	NPD6672	Approved
0.596	Remote Similarity	NPD5737	Approved
0.5957	Remote Similarity	NPD4822	Approved
0.5957	Remote Similarity	NPD4695	Discontinued
0.5957	Remote Similarity	NPD4821	Approved
0.5957	Remote Similarity	NPD4819	Approved
0.5957	Remote Similarity	NPD4820	Approved
0.5938	Remote Similarity	NPD5362	Discontinued

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