NPASS Compound

Structure

CID269530 OpenBabel06191716072D 31 34 0 0 1 0 0 0 0 0999 V2000 -2.6263 -3.0458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9616 3.2162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2757 2.8699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1240 2.3800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4564 -0.5078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8779 1.4528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0933 0.4716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0936 1.4171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2749 -0.0009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8185 -1.4179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6383 1.8905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6366 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0711 -2.2812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0980 2.8314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6375 -0.9454 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4570 1.4175 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8193 1.4180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6377 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8193 -1.4174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2754 1.8901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4567 0.4720 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8190 0.4725 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1313 -2.3797 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6671 3.3869 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8198 -2.3886 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9712 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6368 -0.9445 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4557 -1.4181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.8910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 6 23 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 24 1 0 0 0 0 12 29 1 0 0 0 0 13 25 2 0 0 0 0 13 30 1 0 0 0 0 14 26 2 0 0 0 0 14 31 1 0 0 0 0 15 20 1 0 0 0 0 15 24 1 0 0 0 0 16 19 1 0 0 0 0 16 30 1 6 0 0 0 17 21 1 0 0 0 0 17 22 1 6 0 0 0 18 23 1 6 0 0 0 18 31 1 0 0 0 0 19 22 1 6 0 0 0 19 23 1 0 0 0 0 20 27 2 0 0 0 0 20 29 1 0 0 0 0 22 5 1 6 0 0 0 23 24 1 1 0 0 0 24 28 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.23
Volume:	440.42
LogP:	3.673
LogD:	2.788
LogS:	-4.383
# Rotatable Bonds:	4
TPSA:	99.13
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.526
Synthetic Accessibility Score:	5.02
Fsp3:	0.792
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.063
MDCK Permeability:	6.893184763612226e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.905
Plasma Protein Binding (PPB):	58.13970184326172%
Volume Distribution (VD):	0.972
Pgp-substrate:	53.71762466430664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.233
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.408
CYP3A4-substrate:	0.233

ADMET: Excretion

Clearance (CL):	3.611
Half-life (T1/2):	0.072

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.128
Drug-inuced Liver Injury (DILI):	0.273
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.818
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.534
Carcinogencity:	0.584
Eye Corrosion:	0.957
Eye Irritation:	0.336
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC269530

Natural Product ID:	NPC269530
*Common Name:**	Dorisenone A
IUPAC Name:	[(3aR,3bS,4S,5aS,9aS,9bR,10S)-10-acetyloxy-3a-hydroxy-3b,6,6,9a-tetramethyl-1-oxo-4,5,5a,7,8,9,9b,10-octahydro-3H-naphtho[2,1-e][2]benzofuran-4-yl] acetate
Synonyms:
Standard InCHIKey:	ZYXRRCVRWAEDDD-VAXCZNHBSA-N
Standard InCHI:	InChI=1S/C24H34O7/c1-13(25)30-16-10-15-20(27)29-12-24(15,28)23(6)18(31-14(2)26)11-17-21(3,4)8-7-9-22(17,5)19(16)23/h10,16-19,28H,7-9,11-12H2,1-6H3/t16-,17-,18-,19+,22-,23+,24-/m0/s1
SMILES:	CC(=O)O[C@H]1C=C2C(=O)OC[C@]2([C@]2([C@H]1[C@@]1(C)CCCC([C@@H]1C[C@@H]2OC(=O)C)(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518854
PubChem CID:	10550796
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO25250	Croton verreauxii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29341	Salix triandra	Species	Salicaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	0.21	ug.mL-1	PMID[556205]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.22	ug.mL-1	PMID[556205]

☑ 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 NPC269530 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	222
0.1-0.2	1289
0.2-0.3	3799
0.3-0.4	6551
0.4-0.5	11233
0.5-0.6	8501
0.6-0.7	6643
0.7-0.8	3769
0.8-0.85	554
0.85-0.9	131
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.932	High Similarity	NPC146731
0.9135	High Similarity	NPC296950
0.8991	High Similarity	NPC25909
0.8947	High Similarity	NPC67251
0.8947	High Similarity	NPC469789
0.8919	High Similarity	NPC58662
0.8919	High Similarity	NPC469684
0.8919	High Similarity	NPC473968
0.8899	High Similarity	NPC472002
0.8889	High Similarity	NPC235014
0.8889	High Similarity	NPC5103
0.8879	High Similarity	NPC275539
0.8879	High Similarity	NPC189075
0.887	High Similarity	NPC470922
0.887	High Similarity	NPC8369
0.8857	High Similarity	NPC159533
0.8818	High Similarity	NPC469463
0.8818	High Similarity	NPC469454
0.8818	High Similarity	NPC469496
0.8807	High Similarity	NPC469655
0.8807	High Similarity	NPC474846
0.8807	High Similarity	NPC179798
0.8807	High Similarity	NPC304180
0.8807	High Similarity	NPC469656
0.8793	High Similarity	NPC293112
0.8785	High Similarity	NPC110496
0.8785	High Similarity	NPC187435
0.8785	High Similarity	NPC67321
0.8772	High Similarity	NPC67569
0.8762	High Similarity	NPC295791
0.8761	High Similarity	NPC77689
0.8761	High Similarity	NPC473636
0.875	High Similarity	NPC53396
0.875	High Similarity	NPC98249
0.875	High Similarity	NPC134430
0.8739	High Similarity	NPC117712
0.8727	High Similarity	NPC277769
0.8727	High Similarity	NPC90952
0.8716	High Similarity	NPC478211
0.8716	High Similarity	NPC253906
0.8707	High Similarity	NPC172154
0.8707	High Similarity	NPC24651
0.8707	High Similarity	NPC81736
0.8707	High Similarity	NPC476729
0.8696	High Similarity	NPC23786
0.8696	High Similarity	NPC269642
0.8696	High Similarity	NPC170538
0.8696	High Similarity	NPC470265
0.8679	High Similarity	NPC254202
0.8679	High Similarity	NPC99510
0.8673	High Similarity	NPC478206
0.8673	High Similarity	NPC108581
0.8673	High Similarity	NPC478205
0.8673	High Similarity	NPC284707
0.8649	High Similarity	NPC56448
0.8649	High Similarity	NPC478212
0.8649	High Similarity	NPC471204
0.8649	High Similarity	NPC477126
0.8636	High Similarity	NPC97939
0.8636	High Similarity	NPC247031
0.8636	High Similarity	NPC132790
0.8636	High Similarity	NPC100329
0.8632	High Similarity	NPC473635
0.8624	High Similarity	NPC474243
0.8621	High Similarity	NPC265557
0.8621	High Similarity	NPC18945
0.8621	High Similarity	NPC105926
0.8621	High Similarity	NPC91693
0.8621	High Similarity	NPC11895
0.8611	High Similarity	NPC112780
0.8611	High Similarity	NPC180744
0.8611	High Similarity	NPC230541
0.8609	High Similarity	NPC46570
0.8598	High Similarity	NPC258532
0.8596	High Similarity	NPC475775
0.8596	High Similarity	NPC268958
0.8596	High Similarity	NPC211093
0.8596	High Similarity	NPC473839
0.8596	High Similarity	NPC230513
0.8596	High Similarity	NPC475041
0.8596	High Similarity	NPC476529
0.8585	High Similarity	NPC162973
0.8584	High Similarity	NPC473590
0.8584	High Similarity	NPC23046
0.8584	High Similarity	NPC176513
0.8584	High Similarity	NPC475809
0.8584	High Similarity	NPC478204
0.8584	High Similarity	NPC13713
0.8584	High Similarity	NPC470775
0.8571	High Similarity	NPC471413
0.8559	High Similarity	NPC194951
0.8559	High Similarity	NPC4573
0.8559	High Similarity	NPC12046
0.8559	High Similarity	NPC204556
0.8559	High Similarity	NPC476801
0.8545	High Similarity	NPC478209
0.8545	High Similarity	NPC474567
0.8534	High Similarity	NPC312833
0.8534	High Similarity	NPC107493
0.8532	High Similarity	NPC37628
0.8532	High Similarity	NPC306265
0.8532	High Similarity	NPC151393
0.8522	High Similarity	NPC154491
0.8522	High Similarity	NPC268530
0.8522	High Similarity	NPC109607
0.8522	High Similarity	NPC107338
0.8522	High Similarity	NPC476961
0.8519	High Similarity	NPC469607
0.8519	High Similarity	NPC127609
0.8519	High Similarity	NPC102352
0.8509	High Similarity	NPC50774
0.8509	High Similarity	NPC470776
0.8509	High Similarity	NPC251310
0.8509	High Similarity	NPC709
0.8505	High Similarity	NPC72842
0.8496	Intermediate Similarity	NPC207217
0.8496	Intermediate Similarity	NPC474734
0.8496	Intermediate Similarity	NPC176840
0.8491	Intermediate Similarity	NPC471412
0.8482	Intermediate Similarity	NPC475966
0.8482	Intermediate Similarity	NPC157441
0.8482	Intermediate Similarity	NPC264153
0.8476	Intermediate Similarity	NPC159763
0.8476	Intermediate Similarity	NPC278386
0.8476	Intermediate Similarity	NPC124512
0.8468	Intermediate Similarity	NPC317107
0.8468	Intermediate Similarity	NPC188738
0.8462	Intermediate Similarity	NPC120724
0.8455	Intermediate Similarity	NPC472534
0.8455	Intermediate Similarity	NPC469370
0.8455	Intermediate Similarity	NPC141350
0.8455	Intermediate Similarity	NPC143706
0.8455	Intermediate Similarity	NPC478210
0.8448	Intermediate Similarity	NPC4021
0.8448	Intermediate Similarity	NPC159456
0.8448	Intermediate Similarity	NPC470779
0.844	Intermediate Similarity	NPC78966
0.844	Intermediate Similarity	NPC284732
0.844	Intermediate Similarity	NPC3316
0.844	Intermediate Similarity	NPC144854
0.8435	Intermediate Similarity	NPC475520
0.8435	Intermediate Similarity	NPC42673
0.8435	Intermediate Similarity	NPC470777
0.8426	Intermediate Similarity	NPC65523
0.8426	Intermediate Similarity	NPC283850
0.8421	Intermediate Similarity	NPC167606
0.8421	Intermediate Similarity	NPC286528
0.8421	Intermediate Similarity	NPC470493
0.8421	Intermediate Similarity	NPC97908
0.8421	Intermediate Similarity	NPC470854
0.8421	Intermediate Similarity	NPC470492
0.8421	Intermediate Similarity	NPC122033
0.8421	Intermediate Similarity	NPC27999
0.8421	Intermediate Similarity	NPC55296
0.8421	Intermediate Similarity	NPC312824
0.8421	Intermediate Similarity	NPC477116
0.8421	Intermediate Similarity	NPC473656
0.8421	Intermediate Similarity	NPC20302
0.8421	Intermediate Similarity	NPC183580
0.8421	Intermediate Similarity	NPC140055
0.8421	Intermediate Similarity	NPC284068
0.8421	Intermediate Similarity	NPC474654
0.8421	Intermediate Similarity	NPC287343
0.8417	Intermediate Similarity	NPC231529
0.8417	Intermediate Similarity	NPC473593
0.8411	Intermediate Similarity	NPC183571
0.8411	Intermediate Similarity	NPC476081
0.8411	Intermediate Similarity	NPC165250
0.8407	Intermediate Similarity	NPC67259
0.8407	Intermediate Similarity	NPC147912
0.8403	Intermediate Similarity	NPC287423
0.8403	Intermediate Similarity	NPC42399
0.8396	Intermediate Similarity	NPC47024
0.8393	Intermediate Similarity	NPC265391
0.8393	Intermediate Similarity	NPC42658
0.8393	Intermediate Similarity	NPC152117
0.8393	Intermediate Similarity	NPC470063
0.8393	Intermediate Similarity	NPC234042
0.8393	Intermediate Similarity	NPC317687
0.839	Intermediate Similarity	NPC8374
0.8381	Intermediate Similarity	NPC73911
0.8378	Intermediate Similarity	NPC5284
0.8378	Intermediate Similarity	NPC472666
0.8364	Intermediate Similarity	NPC476802
0.8364	Intermediate Similarity	NPC94377
0.8364	Intermediate Similarity	NPC192813
0.8364	Intermediate Similarity	NPC89171
0.8364	Intermediate Similarity	NPC154608
0.8364	Intermediate Similarity	NPC277017
0.8362	Intermediate Similarity	NPC476962
0.8362	Intermediate Similarity	NPC474585
0.8362	Intermediate Similarity	NPC112038
0.8362	Intermediate Similarity	NPC478051
0.8362	Intermediate Similarity	NPC48692
0.8362	Intermediate Similarity	NPC474370
0.8362	Intermediate Similarity	NPC251226
0.8349	Intermediate Similarity	NPC1679
0.8349	Intermediate Similarity	NPC472655
0.8349	Intermediate Similarity	NPC478208
0.8349	Intermediate Similarity	NPC477125

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 NPC269530 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1539
0.2-0.3	3494
0.3-0.4	2442
0.4-0.5	885
0.5-0.6	310
0.6-0.7	179
0.7-0.8	111
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8476	Intermediate Similarity	NPD4225	Approved
0.8421	Intermediate Similarity	NPD7115	Discovery
0.8125	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8053	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD6319	Approved
0.789	Intermediate Similarity	NPD7639	Approved
0.789	Intermediate Similarity	NPD7640	Approved
0.7876	Intermediate Similarity	NPD6686	Approved
0.7823	Intermediate Similarity	NPD7319	Approved
0.7798	Intermediate Similarity	NPD7638	Approved
0.7788	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD7492	Approved
0.775	Intermediate Similarity	NPD6054	Approved
0.7724	Intermediate Similarity	NPD6616	Approved
0.7724	Intermediate Similarity	NPD7507	Approved
0.7699	Intermediate Similarity	NPD6008	Approved
0.7692	Intermediate Similarity	NPD4632	Approved
0.7686	Intermediate Similarity	NPD8516	Approved
0.7686	Intermediate Similarity	NPD8513	Phase 3
0.7686	Intermediate Similarity	NPD8517	Approved
0.7686	Intermediate Similarity	NPD8515	Approved
0.7661	Intermediate Similarity	NPD7078	Approved
0.7623	Intermediate Similarity	NPD6370	Approved
0.7607	Intermediate Similarity	NPD8297	Approved
0.7603	Intermediate Similarity	NPD6059	Approved
0.76	Intermediate Similarity	NPD7736	Approved
0.7586	Intermediate Similarity	NPD6371	Approved
0.7565	Intermediate Similarity	NPD6899	Approved
0.7565	Intermediate Similarity	NPD6881	Approved
0.7561	Intermediate Similarity	NPD8328	Phase 3
0.7544	Intermediate Similarity	NPD5739	Approved
0.7544	Intermediate Similarity	NPD6675	Approved
0.7544	Intermediate Similarity	NPD6402	Approved
0.7544	Intermediate Similarity	NPD7128	Approved
0.7541	Intermediate Similarity	NPD6016	Approved
0.7541	Intermediate Similarity	NPD6015	Approved
0.7521	Intermediate Similarity	NPD6650	Approved
0.7521	Intermediate Similarity	NPD6649	Approved
0.752	Intermediate Similarity	NPD8293	Discontinued
0.75	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD6372	Approved
0.75	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD5988	Approved
0.7478	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD5697	Approved
0.7436	Intermediate Similarity	NPD6883	Approved
0.7436	Intermediate Similarity	NPD7290	Approved
0.7436	Intermediate Similarity	NPD4634	Approved
0.7436	Intermediate Similarity	NPD7102	Approved
0.7434	Intermediate Similarity	NPD7632	Discontinued
0.7414	Intermediate Similarity	NPD7320	Approved
0.7387	Intermediate Similarity	NPD7902	Approved
0.7381	Intermediate Similarity	NPD8074	Phase 3
0.7373	Intermediate Similarity	NPD6617	Approved
0.7373	Intermediate Similarity	NPD6869	Approved
0.7373	Intermediate Similarity	NPD6847	Approved
0.7373	Intermediate Similarity	NPD8130	Phase 1
0.7355	Intermediate Similarity	NPD6009	Approved
0.735	Intermediate Similarity	NPD6013	Approved
0.735	Intermediate Similarity	NPD6012	Approved
0.735	Intermediate Similarity	NPD6014	Approved
0.7345	Intermediate Similarity	NPD5344	Discontinued
0.7339	Intermediate Similarity	NPD5778	Approved
0.7339	Intermediate Similarity	NPD6399	Phase 3
0.7339	Intermediate Similarity	NPD5779	Approved
0.7333	Intermediate Similarity	NPD1694	Approved
0.7328	Intermediate Similarity	NPD5701	Approved
0.7311	Intermediate Similarity	NPD6053	Discontinued
0.7311	Intermediate Similarity	NPD6882	Approved
0.7281	Intermediate Similarity	NPD5211	Phase 2
0.728	Intermediate Similarity	NPD7604	Phase 2
0.7273	Intermediate Similarity	NPD7748	Approved
0.7265	Intermediate Similarity	NPD6011	Approved
0.7258	Intermediate Similarity	NPD5983	Phase 2
0.7258	Intermediate Similarity	NPD6921	Approved
0.7207	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6412	Phase 2
0.7165	Intermediate Similarity	NPD6336	Discontinued
0.7156	Intermediate Similarity	NPD46	Approved
0.7156	Intermediate Similarity	NPD6698	Approved
0.7155	Intermediate Similarity	NPD5141	Approved
0.7154	Intermediate Similarity	NPD7328	Approved
0.7154	Intermediate Similarity	NPD7327	Approved
0.712	Intermediate Similarity	NPD7503	Approved
0.712	Intermediate Similarity	NPD8033	Approved
0.7117	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7900	Approved
0.7105	Intermediate Similarity	NPD5285	Approved
0.7105	Intermediate Similarity	NPD5286	Approved
0.7105	Intermediate Similarity	NPD6648	Approved
0.7105	Intermediate Similarity	NPD4696	Approved
0.7103	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7516	Approved
0.7091	Intermediate Similarity	NPD7983	Approved
0.7091	Intermediate Similarity	NPD7515	Phase 2
0.7091	Intermediate Similarity	NPD6411	Approved
0.7091	Intermediate Similarity	NPD6079	Approved
0.7083	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4755	Approved
0.7064	Intermediate Similarity	NPD5328	Approved
0.7054	Intermediate Similarity	NPD6033	Approved
0.7048	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD8294	Approved
0.704	Intermediate Similarity	NPD8377	Approved
0.7037	Intermediate Similarity	NPD3573	Approved
0.7023	Intermediate Similarity	NPD7260	Phase 2
0.6992	Remote Similarity	NPD6274	Approved
0.6984	Remote Similarity	NPD8379	Approved
0.6984	Remote Similarity	NPD8335	Approved
0.6984	Remote Similarity	NPD8378	Approved
0.6984	Remote Similarity	NPD8296	Approved
0.6984	Remote Similarity	NPD8380	Approved
0.6983	Remote Similarity	NPD5226	Approved
0.6983	Remote Similarity	NPD5225	Approved
0.6983	Remote Similarity	NPD4633	Approved
0.6983	Remote Similarity	NPD5224	Approved
0.697	Remote Similarity	NPD6845	Suspended
0.6967	Remote Similarity	NPD8133	Approved
0.696	Remote Similarity	NPD7101	Approved
0.696	Remote Similarity	NPD7100	Approved
0.6957	Remote Similarity	NPD4700	Approved
0.6944	Remote Similarity	NPD3618	Phase 1
0.6942	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6084	Phase 2
0.693	Remote Similarity	NPD6083	Phase 2
0.6923	Remote Similarity	NPD5175	Approved
0.6923	Remote Similarity	NPD5174	Approved
0.6909	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6101	Approved
0.6903	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5223	Approved
0.688	Remote Similarity	NPD6335	Approved
0.687	Remote Similarity	NPD5696	Approved
0.6852	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5785	Approved
0.6842	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5222	Approved
0.6842	Remote Similarity	NPD5221	Approved
0.6842	Remote Similarity	NPD4697	Phase 3
0.6814	Remote Similarity	NPD5282	Discontinued
0.68	Remote Similarity	NPD6317	Approved
0.6789	Remote Similarity	NPD6684	Approved
0.6789	Remote Similarity	NPD6409	Approved
0.6789	Remote Similarity	NPD7521	Approved
0.6789	Remote Similarity	NPD7334	Approved
0.6789	Remote Similarity	NPD5330	Approved
0.6789	Remote Similarity	NPD7146	Approved
0.6786	Remote Similarity	NPD8034	Phase 2
0.6786	Remote Similarity	NPD8035	Phase 2
0.6786	Remote Similarity	NPD7637	Suspended
0.6783	Remote Similarity	NPD5173	Approved
0.6754	Remote Similarity	NPD5695	Phase 3
0.6746	Remote Similarity	NPD6314	Approved
0.6746	Remote Similarity	NPD6313	Approved
0.6726	Remote Similarity	NPD4202	Approved
0.6724	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6868	Approved
0.6719	Remote Similarity	NPD6909	Approved
0.6719	Remote Similarity	NPD6908	Approved
0.6696	Remote Similarity	NPD7838	Discovery
0.6694	Remote Similarity	NPD4730	Approved
0.6694	Remote Similarity	NPD4729	Approved
0.6694	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6639	Remote Similarity	NPD4754	Approved
0.6637	Remote Similarity	NPD5693	Phase 1
0.6615	Remote Similarity	NPD6067	Discontinued
0.6606	Remote Similarity	NPD4786	Approved
0.6585	Remote Similarity	NPD5247	Approved
0.6585	Remote Similarity	NPD5250	Approved
0.6585	Remote Similarity	NPD5251	Approved
0.6585	Remote Similarity	NPD5248	Approved
0.6585	Remote Similarity	NPD5249	Phase 3
0.6574	Remote Similarity	NPD3667	Approved
0.6532	Remote Similarity	NPD5216	Approved
0.6532	Remote Similarity	NPD5215	Approved
0.6532	Remote Similarity	NPD5217	Approved
0.6522	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6001	Approved
0.6491	Remote Similarity	NPD5284	Approved
0.6491	Remote Similarity	NPD5281	Approved
0.6486	Remote Similarity	NPD4519	Discontinued
0.6486	Remote Similarity	NPD4623	Approved
0.6466	Remote Similarity	NPD4629	Approved
0.6466	Remote Similarity	NPD5210	Approved
0.646	Remote Similarity	NPD6080	Approved
0.646	Remote Similarity	NPD6904	Approved
0.646	Remote Similarity	NPD6051	Approved
0.646	Remote Similarity	NPD4753	Phase 2
0.646	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.646	Remote Similarity	NPD1695	Approved
0.646	Remote Similarity	NPD6673	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