NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.15
Volume:	272.215
LogP:	1.43
LogD:	1.701
LogS:	-2.843
# Rotatable Bonds:	0
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.512
Synthetic Accessibility Score:	4.661
Fsp3:	0.8
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:	-4.906
MDCK Permeability:	7.639807154191658e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.221
Human Intestinal Absorption (HIA):	0.114
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.279

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.873
Plasma Protein Binding (PPB):	44.76966094970703%
Volume Distribution (VD):	1.005
Pgp-substrate:	58.787109375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.123
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.762
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.155
CYP3A4-inhibitor:	0.112
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	7.635
Half-life (T1/2):	0.283

ADMET: Toxicity

hERG Blockers:	0.156
Human Hepatotoxicity (H-HT):	0.893
Drug-inuced Liver Injury (DILI):	0.168
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.961
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.277
Carcinogencity:	0.109
Eye Corrosion:	0.251
Eye Irritation:	0.353
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC194642

Natural Product ID:	NPC194642
*Common Name:**	Erivanin
IUPAC Name:	(3S,3aS,5aR,6S,8R,9aS,9bS)-6,8-dihydroxy-3,5a-dimethyl-9-methylidene-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran-2-one
Synonyms:	Erivanin
Standard InCHIKey:	PFDGLXOOSQNAKH-JADMEOHCSA-N
Standard InCHI:	InChI=1S/C15H22O4/c1-7-9-4-5-15(3)11(17)6-10(16)8(2)12(15)13(9)19-14(7)18/h7,9-13,16-17H,2,4-6H2,1,3H3/t7-,9-,10+,11-,12+,13-,15-/m0/s1
SMILES:	O[C@@H]1C[C@H](O)[C@]2([C@H](C1=C)[C@H]1OC(=O)[C@H]([C@@H]1CC2)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482833
PubChem CID:	14021308
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO33469	Asteraceae	Family	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18329753]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	1.1	umol/L	PMID[517732]

☑ 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 NPC194642 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	182
0.1-0.2	1317
0.2-0.3	4691
0.3-0.4	10038
0.4-0.5	11823
0.5-0.6	5785
0.6-0.7	6295
0.7-0.8	2352
0.8-0.85	161
0.85-0.9	36
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.954	High Similarity	NPC24861
0.9419	High Similarity	NPC153853
0.9318	High Similarity	NPC225474
0.9318	High Similarity	NPC469596
0.9318	High Similarity	NPC148000
0.9213	High Similarity	NPC157686
0.9213	High Similarity	NPC259042
0.9205	High Similarity	NPC147272
0.9167	High Similarity	NPC97505
0.9111	High Similarity	NPC93245
0.9036	High Similarity	NPC209318
0.9036	High Similarity	NPC223330
0.9011	High Similarity	NPC473963
0.9011	High Similarity	NPC136781
0.8901	High Similarity	NPC284518
0.8901	High Similarity	NPC473964
0.8864	High Similarity	NPC116620
0.8851	High Similarity	NPC305029
0.8851	High Similarity	NPC181103
0.8817	High Similarity	NPC47024
0.8764	High Similarity	NPC475776
0.8736	High Similarity	NPC85698
0.8723	High Similarity	NPC475958
0.871	High Similarity	NPC476807
0.871	High Similarity	NPC476806
0.871	High Similarity	NPC216478
0.8696	High Similarity	NPC228766
0.8696	High Similarity	NPC165528
0.8632	High Similarity	NPC164551
0.8587	High Similarity	NPC90014
0.8542	High Similarity	NPC61442
0.8542	High Similarity	NPC72842
0.8526	High Similarity	NPC242666
0.8526	High Similarity	NPC121218
0.8526	High Similarity	NPC308824
0.8526	High Similarity	NPC253886
0.8523	High Similarity	NPC9231
0.8523	High Similarity	NPC6979
0.8523	High Similarity	NPC185638
0.8495	Intermediate Similarity	NPC256227
0.8469	Intermediate Similarity	NPC78966
0.8469	Intermediate Similarity	NPC284732
0.8462	Intermediate Similarity	NPC198054
0.8444	Intermediate Similarity	NPC253618
0.8444	Intermediate Similarity	NPC77001
0.8438	Intermediate Similarity	NPC476081
0.8434	Intermediate Similarity	NPC92489
0.8427	Intermediate Similarity	NPC175293
0.8421	Intermediate Similarity	NPC477655
0.8404	Intermediate Similarity	NPC10864
0.8404	Intermediate Similarity	NPC474395
0.8391	Intermediate Similarity	NPC243347
0.8384	Intermediate Similarity	NPC37628
0.8372	Intermediate Similarity	NPC475743
0.8372	Intermediate Similarity	NPC475951
0.8367	Intermediate Similarity	NPC37600
0.8351	Intermediate Similarity	NPC156681
0.8351	Intermediate Similarity	NPC99510
0.8333	Intermediate Similarity	NPC295276
0.8333	Intermediate Similarity	NPC39683
0.8333	Intermediate Similarity	NPC111292
0.8333	Intermediate Similarity	NPC474433
0.8316	Intermediate Similarity	NPC89099
0.8316	Intermediate Similarity	NPC20479
0.8316	Intermediate Similarity	NPC28864
0.8316	Intermediate Similarity	NPC162459
0.8316	Intermediate Similarity	NPC98837
0.8316	Intermediate Similarity	NPC38296
0.8316	Intermediate Similarity	NPC38471
0.8315	Intermediate Similarity	NPC477920
0.83	Intermediate Similarity	NPC474243
0.8283	Intermediate Similarity	NPC187435
0.8283	Intermediate Similarity	NPC67321
0.828	Intermediate Similarity	NPC469982
0.828	Intermediate Similarity	NPC473434
0.828	Intermediate Similarity	NPC474841
0.828	Intermediate Similarity	NPC471446
0.8276	Intermediate Similarity	NPC226988
0.8265	Intermediate Similarity	NPC47281
0.8265	Intermediate Similarity	NPC283850
0.8261	Intermediate Similarity	NPC186363
0.8261	Intermediate Similarity	NPC233345
0.8247	Intermediate Similarity	NPC170615
0.8242	Intermediate Similarity	NPC291875
0.8229	Intermediate Similarity	NPC477656
0.8229	Intermediate Similarity	NPC293866
0.8222	Intermediate Similarity	NPC470012
0.8211	Intermediate Similarity	NPC253586
0.8211	Intermediate Similarity	NPC474921
0.8202	Intermediate Similarity	NPC329738
0.8202	Intermediate Similarity	NPC52628
0.8202	Intermediate Similarity	NPC476602
0.8191	Intermediate Similarity	NPC98639
0.8191	Intermediate Similarity	NPC56369
0.8182	Intermediate Similarity	NPC50535
0.8182	Intermediate Similarity	NPC15091
0.8182	Intermediate Similarity	NPC470948
0.8172	Intermediate Similarity	NPC199543
0.8172	Intermediate Similarity	NPC26046
0.8163	Intermediate Similarity	NPC120321
0.8152	Intermediate Similarity	NPC123252
0.8152	Intermediate Similarity	NPC219937
0.8152	Intermediate Similarity	NPC232202
0.8152	Intermediate Similarity	NPC194485
0.8152	Intermediate Similarity	NPC53890
0.8144	Intermediate Similarity	NPC46848
0.8137	Intermediate Similarity	NPC157476
0.8132	Intermediate Similarity	NPC160304
0.8132	Intermediate Similarity	NPC92370
0.8132	Intermediate Similarity	NPC277771
0.8125	Intermediate Similarity	NPC16911
0.8125	Intermediate Similarity	NPC474724
0.8125	Intermediate Similarity	NPC78427
0.8119	Intermediate Similarity	NPC154906
0.8118	Intermediate Similarity	NPC307865
0.8111	Intermediate Similarity	NPC250981
0.8111	Intermediate Similarity	NPC473226
0.8105	Intermediate Similarity	NPC29410
0.8105	Intermediate Similarity	NPC200054
0.8105	Intermediate Similarity	NPC234993
0.8105	Intermediate Similarity	NPC134072
0.81	Intermediate Similarity	NPC230541
0.809	Intermediate Similarity	NPC130966
0.8085	Intermediate Similarity	NPC280804
0.8085	Intermediate Similarity	NPC57117
0.8085	Intermediate Similarity	NPC250075
0.8065	Intermediate Similarity	NPC471747
0.8061	Intermediate Similarity	NPC275990
0.8061	Intermediate Similarity	NPC246736
0.8061	Intermediate Similarity	NPC76866
0.8061	Intermediate Similarity	NPC214946
0.8061	Intermediate Similarity	NPC304832
0.8061	Intermediate Similarity	NPC148628
0.8061	Intermediate Similarity	NPC88203
0.8061	Intermediate Similarity	NPC286519
0.8041	Intermediate Similarity	NPC287676
0.8041	Intermediate Similarity	NPC180733
0.8041	Intermediate Similarity	NPC108371
0.8041	Intermediate Similarity	NPC37047
0.8041	Intermediate Similarity	NPC41971
0.8039	Intermediate Similarity	NPC255655
0.8039	Intermediate Similarity	NPC130302
0.8022	Intermediate Similarity	NPC44538
0.8021	Intermediate Similarity	NPC111348
0.802	Intermediate Similarity	NPC472219
0.802	Intermediate Similarity	NPC306265
0.802	Intermediate Similarity	NPC472217
0.802	Intermediate Similarity	NPC472218
0.8	Intermediate Similarity	NPC476601
0.8	Intermediate Similarity	NPC28791
0.8	Intermediate Similarity	NPC295366
0.8	Intermediate Similarity	NPC210214
0.8	Intermediate Similarity	NPC34768
0.8	Intermediate Similarity	NPC266899
0.8	Intermediate Similarity	NPC183012
0.8	Intermediate Similarity	NPC285927
0.8	Intermediate Similarity	NPC164424
0.7981	Intermediate Similarity	NPC474271
0.798	Intermediate Similarity	NPC87927
0.7979	Intermediate Similarity	NPC294263
0.7978	Intermediate Similarity	NPC471037
0.7959	Intermediate Similarity	NPC52899
0.7959	Intermediate Similarity	NPC81530
0.7959	Intermediate Similarity	NPC163963
0.7959	Intermediate Similarity	NPC289148
0.7959	Intermediate Similarity	NPC75941
0.7957	Intermediate Similarity	NPC100313
0.7957	Intermediate Similarity	NPC48732
0.7957	Intermediate Similarity	NPC158488
0.7941	Intermediate Similarity	NPC143706
0.7941	Intermediate Similarity	NPC472534
0.7941	Intermediate Similarity	NPC141350
0.7938	Intermediate Similarity	NPC164349
0.7938	Intermediate Similarity	NPC473155
0.7938	Intermediate Similarity	NPC474793
0.7938	Intermediate Similarity	NPC471038
0.7938	Intermediate Similarity	NPC119036
0.7935	Intermediate Similarity	NPC16377
0.7935	Intermediate Similarity	NPC136879
0.7921	Intermediate Similarity	NPC59530
0.7921	Intermediate Similarity	NPC143609
0.7921	Intermediate Similarity	NPC251824
0.7921	Intermediate Similarity	NPC86852
0.7921	Intermediate Similarity	NPC471246
0.7917	Intermediate Similarity	NPC13949
0.7917	Intermediate Similarity	NPC116457
0.7912	Intermediate Similarity	NPC329692
0.7912	Intermediate Similarity	NPC187545
0.7912	Intermediate Similarity	NPC475684
0.7905	Intermediate Similarity	NPC117712
0.79	Intermediate Similarity	NPC301787
0.79	Intermediate Similarity	NPC84928
0.79	Intermediate Similarity	NPC258532
0.7895	Intermediate Similarity	NPC277399
0.7895	Intermediate Similarity	NPC159365
0.7895	Intermediate Similarity	NPC47853
0.7895	Intermediate Similarity	NPC3359
0.7889	Intermediate Similarity	NPC473299
0.7889	Intermediate Similarity	NPC299963
0.7889	Intermediate Similarity	NPC470011

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 NPC194642 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1742
0.2-0.3	3846
0.3-0.4	2232
0.4-0.5	644
0.5-0.6	230
0.6-0.7	240
0.7-0.8	54
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
0.7872	Intermediate Similarity	NPD8035	Phase 2
0.7872	Intermediate Similarity	NPD8034	Phase 2
0.7609	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD6399	Phase 3
0.7576	Intermediate Similarity	NPD4225	Approved
0.75	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.74	Intermediate Similarity	NPD7638	Approved
0.7333	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7902	Approved
0.7264	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6118	Approved
0.7222	Intermediate Similarity	NPD6115	Approved
0.7222	Intermediate Similarity	NPD6114	Approved
0.7222	Intermediate Similarity	NPD6697	Approved
0.7196	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7748	Approved
0.7158	Intermediate Similarity	NPD3618	Phase 1
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD7637	Suspended
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD7515	Phase 2
0.7143	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.7111	Intermediate Similarity	NPD6116	Phase 1
0.7103	Intermediate Similarity	NPD6372	Approved
0.7103	Intermediate Similarity	NPD6373	Approved
0.7097	Intermediate Similarity	NPD3667	Approved
0.7075	Intermediate Similarity	NPD5697	Approved
0.7075	Intermediate Similarity	NPD5701	Approved
0.7071	Intermediate Similarity	NPD5778	Approved
0.7071	Intermediate Similarity	NPD5779	Approved
0.7019	Intermediate Similarity	NPD7632	Discontinued
0.7009	Intermediate Similarity	NPD7320	Approved
0.7009	Intermediate Similarity	NPD6881	Approved
0.7009	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8133	Approved
0.7	Intermediate Similarity	NPD7900	Approved
0.7	Intermediate Similarity	NPD6117	Approved
0.6972	Remote Similarity	NPD6649	Approved
0.6972	Remote Similarity	NPD6650	Approved
0.6964	Remote Similarity	NPD7115	Discovery
0.6947	Remote Similarity	NPD4786	Approved
0.6947	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6012	Approved
0.6944	Remote Similarity	NPD6013	Approved
0.6944	Remote Similarity	NPD6014	Approved
0.6916	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7102	Approved
0.6881	Remote Similarity	NPD7290	Approved
0.6881	Remote Similarity	NPD6883	Approved
0.6875	Remote Similarity	NPD1694	Approved
0.6857	Remote Similarity	NPD5211	Phase 2
0.6852	Remote Similarity	NPD6686	Approved
0.6852	Remote Similarity	NPD6011	Approved
0.6842	Remote Similarity	NPD6695	Phase 3
0.6818	Remote Similarity	NPD6847	Approved
0.6818	Remote Similarity	NPD6869	Approved
0.6818	Remote Similarity	NPD8130	Phase 1
0.6818	Remote Similarity	NPD6617	Approved
0.68	Remote Similarity	NPD6411	Approved
0.6796	Remote Similarity	NPD6084	Phase 2
0.6796	Remote Similarity	NPD6083	Phase 2
0.6796	Remote Similarity	NPD4755	Approved
0.6778	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5328	Approved
0.6765	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6882	Approved
0.6757	Remote Similarity	NPD8297	Approved
0.6737	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4202	Approved
0.6731	Remote Similarity	NPD5696	Approved
0.6729	Remote Similarity	NPD5141	Approved
0.6703	Remote Similarity	NPD3703	Phase 2
0.6699	Remote Similarity	NPD4697	Phase 3
0.6696	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6319	Approved
0.6634	Remote Similarity	NPD6079	Approved
0.6633	Remote Similarity	NPD5330	Approved
0.6633	Remote Similarity	NPD6409	Approved
0.6633	Remote Similarity	NPD6684	Approved
0.6633	Remote Similarity	NPD7521	Approved
0.6633	Remote Similarity	NPD7146	Approved
0.6633	Remote Similarity	NPD7334	Approved
0.6606	Remote Similarity	NPD6412	Phase 2
0.6602	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5695	Phase 3
0.66	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6101	Approved
0.6598	Remote Similarity	NPD3668	Phase 3
0.6598	Remote Similarity	NPD3665	Phase 1
0.6598	Remote Similarity	NPD3133	Approved
0.6598	Remote Similarity	NPD3666	Approved
0.6596	Remote Similarity	NPD6929	Approved
0.6581	Remote Similarity	NPD6921	Approved
0.6579	Remote Similarity	NPD6274	Approved
0.6566	Remote Similarity	NPD7524	Approved
0.6566	Remote Similarity	NPD7750	Discontinued
0.6555	Remote Similarity	NPD7492	Approved
0.6542	Remote Similarity	NPD5226	Approved
0.6542	Remote Similarity	NPD5225	Approved
0.6542	Remote Similarity	NPD5224	Approved
0.6542	Remote Similarity	NPD4633	Approved
0.6538	Remote Similarity	NPD5222	Approved
0.6538	Remote Similarity	NPD5221	Approved
0.6538	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7525	Registered
0.6526	Remote Similarity	NPD6931	Approved
0.6526	Remote Similarity	NPD6930	Phase 2
0.6522	Remote Similarity	NPD6009	Approved
0.6517	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5282	Discontinued
0.65	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6616	Approved
0.65	Remote Similarity	NPD6903	Approved
0.65	Remote Similarity	NPD7507	Approved
0.65	Remote Similarity	NPD5737	Approved
0.65	Remote Similarity	NPD6672	Approved
0.6496	Remote Similarity	NPD6059	Approved
0.6496	Remote Similarity	NPD6054	Approved
0.6495	Remote Similarity	NPD7154	Phase 3
0.6495	Remote Similarity	NPD4788	Approved
0.6481	Remote Similarity	NPD5175	Approved
0.6481	Remote Similarity	NPD5174	Approved
0.6476	Remote Similarity	NPD5173	Approved
0.6475	Remote Similarity	NPD7319	Approved
0.6471	Remote Similarity	NPD8328	Phase 3
0.6465	Remote Similarity	NPD4249	Approved
0.6449	Remote Similarity	NPD5223	Approved
0.6449	Remote Similarity	NPD5344	Discontinued
0.6449	Remote Similarity	NPD1700	Approved
0.6446	Remote Similarity	NPD8293	Discontinued
0.6446	Remote Similarity	NPD7078	Approved
0.6441	Remote Similarity	NPD5983	Phase 2
0.6441	Remote Similarity	NPD6016	Approved
0.6441	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6015	Approved
0.6436	Remote Similarity	NPD4753	Phase 2
0.6429	Remote Similarity	NPD4634	Approved
0.6421	Remote Similarity	NPD7645	Phase 2
0.641	Remote Similarity	NPD7100	Approved
0.641	Remote Similarity	NPD7101	Approved
0.64	Remote Similarity	NPD4250	Approved
0.64	Remote Similarity	NPD4251	Approved
0.64	Remote Similarity	NPD3573	Approved
0.6393	Remote Similarity	NPD7736	Approved
0.6387	Remote Similarity	NPD5988	Approved
0.6387	Remote Similarity	NPD6370	Approved
0.6383	Remote Similarity	NPD5776	Phase 2
0.6383	Remote Similarity	NPD6925	Approved
0.6379	Remote Similarity	NPD6317	Approved
0.6374	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD46	Approved
0.6373	Remote Similarity	NPD6698	Approved
0.6364	Remote Similarity	NPD4767	Approved
0.6364	Remote Similarity	NPD4768	Approved
0.6354	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6001	Approved
0.6344	Remote Similarity	NPD3702	Approved
0.6333	Remote Similarity	NPD7604	Phase 2
0.633	Remote Similarity	NPD4754	Approved
0.6327	Remote Similarity	NPD5362	Discontinued
0.6325	Remote Similarity	NPD6335	Approved
0.6325	Remote Similarity	NPD7327	Approved
0.6325	Remote Similarity	NPD6313	Approved
0.6325	Remote Similarity	NPD6314	Approved
0.6325	Remote Similarity	NPD7328	Approved
0.6316	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6053	Discontinued
0.6316	Remote Similarity	NPD7145	Approved
0.6311	Remote Similarity	NPD7087	Discontinued
0.6311	Remote Similarity	NPD5281	Approved
0.6311	Remote Similarity	NPD7983	Approved
0.6311	Remote Similarity	NPD5284	Approved
0.6303	Remote Similarity	NPD6909	Approved
0.6303	Remote Similarity	NPD8516	Approved
0.6303	Remote Similarity	NPD6908	Approved
0.6303	Remote Similarity	NPD8517	Approved
0.6303	Remote Similarity	NPD8515	Approved
0.6303	Remote Similarity	NPD8513	Phase 3
0.63	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6868	Approved
0.6286	Remote Similarity	NPD5210	Approved
0.6286	Remote Similarity	NPD4629	Approved
0.6283	Remote Similarity	NPD6371	Approved
0.6277	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD1695	Approved
0.6271	Remote Similarity	NPD7516	Approved
0.625	Remote Similarity	NPD5128	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