NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	269.578
LogP:	1.706
LogD:	1.498
LogS:	-2.316
# Rotatable Bonds:	0
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.531
Synthetic Accessibility Score:	4.673
Fsp3:	0.733
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:	-4.757
MDCK Permeability:	1.4676294995297212e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.032
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.944
Plasma Protein Binding (PPB):	45.17622375488281%
Volume Distribution (VD):	1.016
Pgp-substrate:	58.410186767578125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.2
CYP1A2-substrate:	0.376
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.519
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.231
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.258

ADMET: Excretion

Clearance (CL):	9.7
Half-life (T1/2):	0.575

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.131
Drug-inuced Liver Injury (DILI):	0.137
AMES Toxicity:	0.221
Rat Oral Acute Toxicity:	0.814
Maximum Recommended Daily Dose:	0.587
Skin Sensitization:	0.435
Carcinogencity:	0.361
Eye Corrosion:	0.337
Eye Irritation:	0.082
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC473331

Natural Product ID:	NPC473331
*Common Name:**	3-Hydroxydamsin
IUPAC Name:	(3aS,6S,6aS,8R,9aR,9bR)-8-hydroxy-6,9a-dimethyl-3-methylidene-3a,4,5,6,6a,7,8,9b-octahydroazuleno[8,7-b]furan-2,9-dione
Synonyms:	3-Hydroxydamsin
Standard InCHIKey:	XCOWSXJLBZJEMH-FBRYINLUSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-7-4-5-9-8(2)14(18)19-13(9)15(3)10(7)6-11(16)12(15)17/h7,9-11,13,16H,2,4-6H2,1,3H3/t7-,9-,10-,11+,13+,15-/m0/s1
SMILES:	CC1CCC2C(C3(C1CC(C3=O)O)C)OC(=O)C2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400949
PubChem CID:	44444896
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:0002046] Ambrosanolides and secoambrosanolides

*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	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	pED50	=	5.0	n.a.	PMID[545518]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.65	ug ml-1	PMID[545518]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	10.0	umol/L	PMID[545519]

☑ 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 NPC473331 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	265
0.1-0.2	1895
0.2-0.3	6742
0.3-0.4	14056
0.4-0.5	9813
0.5-0.6	6595
0.6-0.7	2870
0.7-0.8	364
0.8-0.85	36
0.85-0.9	42
0.9-0.95	18
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9438	High Similarity	NPC200237
0.9341	High Similarity	NPC142529
0.9341	High Similarity	NPC91771
0.9222	High Similarity	NPC153590
0.9101	High Similarity	NPC168679
0.9101	High Similarity	NPC155935
0.9101	High Similarity	NPC12872
0.9032	High Similarity	NPC311904
0.9011	High Similarity	NPC473273
0.9011	High Similarity	NPC308656
0.9011	High Similarity	NPC60386
0.9011	High Similarity	NPC473234
0.9011	High Similarity	NPC473263
0.9	High Similarity	NPC19087
0.9	High Similarity	NPC35809
0.9	High Similarity	NPC297474
0.9	High Similarity	NPC54065
0.8977	High Similarity	NPC56593
0.8947	High Similarity	NPC171759
0.8901	High Similarity	NPC63193
0.8901	High Similarity	NPC286341
0.8901	High Similarity	NPC191339
0.8901	High Similarity	NPC57304
0.8901	High Similarity	NPC29821
0.8901	High Similarity	NPC35959
0.8901	High Similarity	NPC184063
0.8901	High Similarity	NPC171360
0.8901	High Similarity	NPC133888
0.8901	High Similarity	NPC293001
0.8889	High Similarity	NPC38392
0.8876	High Similarity	NPC118601
0.883	High Similarity	NPC474313
0.8817	High Similarity	NPC163228
0.8778	High Similarity	NPC217983
0.8778	High Similarity	NPC207114
0.8778	High Similarity	NPC178875
0.8764	High Similarity	NPC187661
0.875	High Similarity	NPC194859
0.875	High Similarity	NPC224386
0.8681	High Similarity	NPC215556
0.8667	High Similarity	NPC201658
0.8632	High Similarity	NPC108475
0.8632	High Similarity	NPC170143
0.8632	High Similarity	NPC213947
0.8587	High Similarity	NPC216284
0.8571	High Similarity	NPC79549
0.8556	High Similarity	NPC304558
0.8556	High Similarity	NPC236692
0.8556	High Similarity	NPC238593
0.8556	High Similarity	NPC309757
0.8526	High Similarity	NPC24956
0.8526	High Similarity	NPC18019
0.8526	High Similarity	NPC476009
0.8526	High Similarity	NPC126156
0.8523	High Similarity	NPC246076
0.8506	High Similarity	NPC6823
0.8462	Intermediate Similarity	NPC24728
0.8444	Intermediate Similarity	NPC300082
0.8444	Intermediate Similarity	NPC204105
0.8444	Intermediate Similarity	NPC284534
0.8427	Intermediate Similarity	NPC54468
0.8427	Intermediate Similarity	NPC128246
0.8421	Intermediate Similarity	NPC475900
0.8409	Intermediate Similarity	NPC126248
0.8404	Intermediate Similarity	NPC475788
0.837	Intermediate Similarity	NPC471149
0.8352	Intermediate Similarity	NPC470242
0.8298	Intermediate Similarity	NPC155215
0.8298	Intermediate Similarity	NPC475925
0.8295	Intermediate Similarity	NPC293418
0.8295	Intermediate Similarity	NPC290508
0.8295	Intermediate Similarity	NPC73052
0.828	Intermediate Similarity	NPC283409
0.8247	Intermediate Similarity	NPC471150
0.8229	Intermediate Similarity	NPC476053
0.8229	Intermediate Similarity	NPC472873
0.8229	Intermediate Similarity	NPC48803
0.8229	Intermediate Similarity	NPC90121
0.8229	Intermediate Similarity	NPC193645
0.8229	Intermediate Similarity	NPC275960
0.8222	Intermediate Similarity	NPC111409
0.8218	Intermediate Similarity	NPC44004
0.8211	Intermediate Similarity	NPC258216
0.8211	Intermediate Similarity	NPC135776
0.8202	Intermediate Similarity	NPC47635
0.8152	Intermediate Similarity	NPC64153
0.8119	Intermediate Similarity	NPC203659
0.8105	Intermediate Similarity	NPC131209
0.81	Intermediate Similarity	NPC474747
0.81	Intermediate Similarity	NPC225353
0.809	Intermediate Similarity	NPC51507
0.8081	Intermediate Similarity	NPC471381
0.8065	Intermediate Similarity	NPC270270
0.8061	Intermediate Similarity	NPC477949
0.8061	Intermediate Similarity	NPC169205
0.8041	Intermediate Similarity	NPC52044
0.8041	Intermediate Similarity	NPC213698
0.8041	Intermediate Similarity	NPC170120
0.8022	Intermediate Similarity	NPC245665
0.802	Intermediate Similarity	NPC473148
0.802	Intermediate Similarity	NPC475871
0.802	Intermediate Similarity	NPC110989
0.802	Intermediate Similarity	NPC475945
0.798	Intermediate Similarity	NPC141191
0.7979	Intermediate Similarity	NPC91248
0.7959	Intermediate Similarity	NPC185553
0.7959	Intermediate Similarity	NPC76862
0.7959	Intermediate Similarity	NPC158416
0.7959	Intermediate Similarity	NPC39859
0.7959	Intermediate Similarity	NPC470883
0.7957	Intermediate Similarity	NPC67493
0.7955	Intermediate Similarity	NPC208223
0.7938	Intermediate Similarity	NPC323008
0.7938	Intermediate Similarity	NPC470013
0.7938	Intermediate Similarity	NPC198853
0.7938	Intermediate Similarity	NPC470010
0.7938	Intermediate Similarity	NPC127019
0.7938	Intermediate Similarity	NPC262133
0.7917	Intermediate Similarity	NPC133698
0.79	Intermediate Similarity	NPC186861
0.7895	Intermediate Similarity	NPC472872
0.7895	Intermediate Similarity	NPC32922
0.7895	Intermediate Similarity	NPC173926
0.7889	Intermediate Similarity	NPC156658
0.7889	Intermediate Similarity	NPC258965
0.7879	Intermediate Similarity	NPC161493
0.7872	Intermediate Similarity	NPC190753
0.7872	Intermediate Similarity	NPC186148
0.7857	Intermediate Similarity	NPC67584
0.7843	Intermediate Similarity	NPC221421
0.7835	Intermediate Similarity	NPC475488
0.7826	Intermediate Similarity	NPC215294
0.7822	Intermediate Similarity	NPC474742
0.7822	Intermediate Similarity	NPC477950
0.7816	Intermediate Similarity	NPC143979
0.7816	Intermediate Similarity	NPC320537
0.7812	Intermediate Similarity	NPC301969
0.7812	Intermediate Similarity	NPC71533
0.7812	Intermediate Similarity	NPC37607
0.7812	Intermediate Similarity	NPC106510
0.78	Intermediate Similarity	NPC249171
0.78	Intermediate Similarity	NPC49833
0.78	Intermediate Similarity	NPC45125
0.7789	Intermediate Similarity	NPC53158
0.7789	Intermediate Similarity	NPC177629
0.7789	Intermediate Similarity	NPC58219
0.7788	Intermediate Similarity	NPC26617
0.7778	Intermediate Similarity	NPC213078
0.7767	Intermediate Similarity	NPC474741
0.7755	Intermediate Similarity	NPC167219
0.7755	Intermediate Similarity	NPC190294
0.7755	Intermediate Similarity	NPC477131
0.7745	Intermediate Similarity	NPC80144
0.7732	Intermediate Similarity	NPC74103
0.7732	Intermediate Similarity	NPC70595
0.7732	Intermediate Similarity	NPC123177
0.7732	Intermediate Similarity	NPC150978
0.7714	Intermediate Similarity	NPC255082
0.7714	Intermediate Similarity	NPC68248
0.7708	Intermediate Similarity	NPC92974
0.7708	Intermediate Similarity	NPC474951
0.7708	Intermediate Similarity	NPC117405
0.7708	Intermediate Similarity	NPC52198
0.7708	Intermediate Similarity	NPC268298
0.77	Intermediate Similarity	NPC181151
0.77	Intermediate Similarity	NPC304445
0.77	Intermediate Similarity	NPC236580
0.7692	Intermediate Similarity	NPC54737
0.7677	Intermediate Similarity	NPC304886
0.7677	Intermediate Similarity	NPC469873
0.767	Intermediate Similarity	NPC475873
0.766	Intermediate Similarity	NPC33570
0.766	Intermediate Similarity	NPC21471
0.766	Intermediate Similarity	NPC235792
0.7653	Intermediate Similarity	NPC475302
0.7647	Intermediate Similarity	NPC67296
0.7647	Intermediate Similarity	NPC150923
0.7647	Intermediate Similarity	NPC201718
0.7634	Intermediate Similarity	NPC128429
0.7629	Intermediate Similarity	NPC253144
0.7629	Intermediate Similarity	NPC246173
0.7629	Intermediate Similarity	NPC129419
0.7624	Intermediate Similarity	NPC221615
0.7624	Intermediate Similarity	NPC54843
0.7604	Intermediate Similarity	NPC224652
0.7604	Intermediate Similarity	NPC202672
0.7596	Intermediate Similarity	NPC100487
0.7582	Intermediate Similarity	NPC19841
0.7579	Intermediate Similarity	NPC474949
0.7579	Intermediate Similarity	NPC475019
0.7579	Intermediate Similarity	NPC162071
0.7576	Intermediate Similarity	NPC469596
0.7576	Intermediate Similarity	NPC225474
0.7576	Intermediate Similarity	NPC148000
0.7573	Intermediate Similarity	NPC164551
0.7553	Intermediate Similarity	NPC156485
0.7551	Intermediate Similarity	NPC221282
0.7551	Intermediate Similarity	NPC20713
0.7551	Intermediate Similarity	NPC208886
0.7551	Intermediate Similarity	NPC284185

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 NPC473331 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	2620
0.2-0.3	3842
0.3-0.4	1613
0.4-0.5	457
0.5-0.6	238
0.6-0.7	56
0.7-0.8	5
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
0.8229	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD1695	Approved
0.7449	Intermediate Similarity	NPD5785	Approved
0.7407	Intermediate Similarity	NPD6371	Approved
0.7228	Intermediate Similarity	NPD5282	Discontinued
0.6939	Remote Similarity	NPD5363	Approved
0.6875	Remote Similarity	NPD5369	Approved
0.6869	Remote Similarity	NPD5786	Approved
0.6804	Remote Similarity	NPD4269	Approved
0.6804	Remote Similarity	NPD4270	Approved
0.67	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD6053	Discontinued
0.6636	Remote Similarity	NPD7638	Approved
0.6634	Remote Similarity	NPD4250	Approved
0.6634	Remote Similarity	NPD4251	Approved
0.6633	Remote Similarity	NPD6435	Approved
0.6612	Remote Similarity	NPD7492	Approved
0.6607	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4252	Approved
0.6577	Remote Similarity	NPD6008	Approved
0.6574	Remote Similarity	NPD7640	Approved
0.6574	Remote Similarity	NPD7639	Approved
0.6566	Remote Similarity	NPD5362	Discontinued
0.6557	Remote Similarity	NPD6616	Approved
0.6555	Remote Similarity	NPD6054	Approved
0.6555	Remote Similarity	NPD6319	Approved
0.6518	Remote Similarity	NPD5697	Approved
0.6504	Remote Similarity	NPD7078	Approved
0.65	Remote Similarity	NPD6015	Approved
0.65	Remote Similarity	NPD6016	Approved
0.6481	Remote Similarity	NPD4225	Approved
0.6476	Remote Similarity	NPD6399	Phase 3
0.6466	Remote Similarity	NPD4632	Approved
0.646	Remote Similarity	NPD6881	Approved
0.646	Remote Similarity	NPD7320	Approved
0.646	Remote Similarity	NPD6899	Approved
0.646	Remote Similarity	NPD6011	Approved
0.6452	Remote Similarity	NPD7736	Approved
0.6446	Remote Similarity	NPD6370	Approved
0.6446	Remote Similarity	NPD5988	Approved
0.6442	Remote Similarity	NPD6698	Approved
0.6442	Remote Similarity	NPD46	Approved
0.6436	Remote Similarity	NPD1694	Approved
0.6435	Remote Similarity	NPD6649	Approved
0.6435	Remote Similarity	NPD6650	Approved
0.6429	Remote Similarity	NPD6675	Approved
0.6429	Remote Similarity	NPD6402	Approved
0.6429	Remote Similarity	NPD5739	Approved
0.6429	Remote Similarity	NPD7128	Approved
0.6429	Remote Similarity	NPD5368	Approved
0.6417	Remote Similarity	NPD6059	Approved
0.6404	Remote Similarity	NPD6373	Approved
0.6404	Remote Similarity	NPD6012	Approved
0.6404	Remote Similarity	NPD6014	Approved
0.6404	Remote Similarity	NPD6013	Approved
0.6404	Remote Similarity	NPD6372	Approved
0.6392	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6083	Phase 2
0.6389	Remote Similarity	NPD6084	Phase 2
0.6381	Remote Similarity	NPD7983	Approved
0.6372	Remote Similarity	NPD5701	Approved
0.6371	Remote Similarity	NPD8293	Discontinued
0.6355	Remote Similarity	NPD5695	Phase 3
0.6348	Remote Similarity	NPD7290	Approved
0.6348	Remote Similarity	NPD7102	Approved
0.6348	Remote Similarity	NPD6883	Approved
0.633	Remote Similarity	NPD5696	Approved
0.6321	Remote Similarity	NPD5778	Approved
0.6321	Remote Similarity	NPD5779	Approved
0.6316	Remote Similarity	NPD6686	Approved
0.6303	Remote Similarity	NPD6009	Approved
0.6303	Remote Similarity	NPD7115	Discovery
0.6293	Remote Similarity	NPD6847	Approved
0.6293	Remote Similarity	NPD6869	Approved
0.6293	Remote Similarity	NPD6617	Approved
0.6293	Remote Similarity	NPD8130	Phase 1
0.6263	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6845	Suspended
0.6239	Remote Similarity	NPD8297	Approved
0.6239	Remote Similarity	NPD6882	Approved
0.6238	Remote Similarity	NPD7154	Phase 3
0.623	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5983	Phase 2
0.6226	Remote Similarity	NPD5693	Phase 1
0.6226	Remote Similarity	NPD8035	Phase 2
0.6226	Remote Similarity	NPD8034	Phase 2
0.6226	Remote Similarity	NPD7637	Suspended
0.6226	Remote Similarity	NPD6411	Approved
0.6224	Remote Similarity	NPD4238	Approved
0.6224	Remote Similarity	NPD4802	Phase 2
0.6216	Remote Similarity	NPD1700	Approved
0.6207	Remote Similarity	NPD4634	Approved
0.6195	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD7260	Phase 2
0.6161	Remote Similarity	NPD5211	Phase 2
0.6161	Remote Similarity	NPD7632	Discontinued
0.6154	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD7319	Approved
0.6139	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5209	Approved
0.6132	Remote Similarity	NPD7838	Discovery
0.6129	Remote Similarity	NPD7604	Phase 2
0.6126	Remote Similarity	NPD4696	Approved
0.6126	Remote Similarity	NPD5285	Approved
0.6126	Remote Similarity	NPD5286	Approved
0.61	Remote Similarity	NPD4819	Approved
0.61	Remote Similarity	NPD4822	Approved
0.61	Remote Similarity	NPD4820	Approved
0.61	Remote Similarity	NPD4821	Approved
0.6095	Remote Similarity	NPD6903	Approved
0.6095	Remote Similarity	NPD5737	Approved
0.6095	Remote Similarity	NPD6672	Approved
0.6091	Remote Similarity	NPD4755	Approved
0.6087	Remote Similarity	NPD6412	Phase 2
0.6083	Remote Similarity	NPD6274	Approved
0.6078	Remote Similarity	NPD5331	Approved
0.6078	Remote Similarity	NPD5332	Approved
0.6078	Remote Similarity	NPD4788	Approved
0.6071	Remote Similarity	NPD5223	Approved
0.6063	Remote Similarity	NPD6033	Approved
0.6061	Remote Similarity	NPD4271	Approved
0.6061	Remote Similarity	NPD4268	Approved
0.6058	Remote Similarity	NPD5279	Phase 3
0.6058	Remote Similarity	NPD7146	Approved
0.6058	Remote Similarity	NPD6409	Approved
0.6058	Remote Similarity	NPD7334	Approved
0.6058	Remote Similarity	NPD5330	Approved
0.6058	Remote Similarity	NPD7521	Approved
0.6058	Remote Similarity	NPD6684	Approved
0.6055	Remote Similarity	NPD5210	Approved
0.6055	Remote Similarity	NPD4629	Approved
0.6053	Remote Similarity	NPD5141	Approved
0.605	Remote Similarity	NPD8133	Approved
0.604	Remote Similarity	NPD4790	Discontinued
0.6038	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD4753	Phase 2
0.6038	Remote Similarity	NPD6101	Approved
0.6033	Remote Similarity	NPD6317	Approved
0.6032	Remote Similarity	NPD7507	Approved
0.6032	Remote Similarity	NPD6336	Discontinued
0.6019	Remote Similarity	NPD3133	Approved
0.6019	Remote Similarity	NPD3666	Approved
0.6019	Remote Similarity	NPD3665	Phase 1
0.6018	Remote Similarity	NPD5225	Approved
0.6018	Remote Similarity	NPD5226	Approved
0.6018	Remote Similarity	NPD4633	Approved
0.6018	Remote Similarity	NPD5224	Approved
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5221	Approved
0.5984	Remote Similarity	NPD6314	Approved
0.5984	Remote Similarity	NPD6313	Approved
0.5984	Remote Similarity	NPD6335	Approved
0.5982	Remote Similarity	NPD4700	Approved
0.598	Remote Similarity	NPD3667	Approved
0.5969	Remote Similarity	NPD5956	Approved
0.5968	Remote Similarity	NPD8267	Approved
0.5968	Remote Similarity	NPD8268	Approved
0.5968	Remote Similarity	NPD8266	Approved
0.5968	Remote Similarity	NPD6921	Approved
0.5968	Remote Similarity	NPD8269	Approved
0.5965	Remote Similarity	NPD5175	Approved
0.5965	Remote Similarity	NPD5174	Approved
0.5962	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD5173	Approved
0.5943	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD7100	Approved
0.5935	Remote Similarity	NPD7101	Approved
0.5926	Remote Similarity	NPD5284	Approved
0.5926	Remote Similarity	NPD5281	Approved
0.5909	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD3618	Phase 1
0.5896	Remote Similarity	NPD6334	Approved
0.5896	Remote Similarity	NPD6333	Approved
0.5893	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6673	Approved
0.5888	Remote Similarity	NPD6904	Approved
0.5888	Remote Similarity	NPD6080	Approved
0.5873	Remote Similarity	NPD8328	Phase 3
0.5865	Remote Similarity	NPD4786	Approved
0.5856	Remote Similarity	NPD7839	Suspended
0.5847	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.584	Remote Similarity	NPD8513	Phase 3
0.584	Remote Similarity	NPD8516	Approved
0.584	Remote Similarity	NPD8515	Approved
0.584	Remote Similarity	NPD8517	Approved
0.5833	Remote Similarity	NPD5207	Approved
0.5833	Remote Similarity	NPD5692	Phase 3
0.5826	Remote Similarity	NPD4754	Approved
0.582	Remote Similarity	NPD6868	Approved
0.5804	Remote Similarity	NPD7902	Approved
0.5798	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD229	Approved
0.5784	Remote Similarity	NPD4695	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