NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	590.38
Volume:	610.33
LogP:	3.332
LogD:	3.369
LogS:	-4.158
# Rotatable Bonds:	7
TPSA:	136.68
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.285
Synthetic Accessibility Score:	5.476
Fsp3:	0.912
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.125
MDCK Permeability:	6.155458322609775e-06
Pgp-inhibitor:	0.983
Pgp-substrate:	0.755
Human Intestinal Absorption (HIA):	0.888
20% Bioavailability (F20%):	0.808
30% Bioavailability (F30%):	0.264

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.295
Plasma Protein Binding (PPB):	74.8263931274414%
Volume Distribution (VD):	0.619
Pgp-substrate:	5.612489223480225%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.437
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.395
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.383
CYP3A4-substrate:	0.124

ADMET: Excretion

Clearance (CL):	4.149
Half-life (T1/2):	0.894

ADMET: Toxicity

hERG Blockers:	0.547
Human Hepatotoxicity (H-HT):	0.246
Drug-inuced Liver Injury (DILI):	0.293
AMES Toxicity:	0.163
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.726
Skin Sensitization:	0.92
Carcinogencity:	0.499
Eye Corrosion:	0.004
Eye Irritation:	0.021
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: NPC477944

Natural Product ID:	NPC477944
*Common Name:**	(1S,2S,4S,7S,8R,9S,12S,13R)-6-hydroxy-7,9,13-trimethyl-6-[3-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]pentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one
IUPAC Name:	(1S,2S,4S,7S,8R,9S,12S,13R)-6-hydroxy-7,9,13-trimethyl-6-[3-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]pentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one
Synonyms:
Standard InCHIKey:	KVQPFNFPPHHRIE-RPWMYJERSA-N
Standard InCHI:	InChI=1S/C34H54O8/c1-18(17-41-31-30(39)29(38)28(37)26(16-35)42-31)7-12-34(40)15-20-13-25-23-6-5-21-14-22(36)8-10-32(21,3)24(23)9-11-33(25,4)27(20)19(34)2/h14,18-20,23-31,35,37-40H,5-13,15-17H2,1-4H3/t18?,19-,20-,23+,24-,25-,26+,27-,28+,29-,30+,31+,32-,33-,34?/m0/s1
SMILES:	C[C@H]1[C@H]2[C@@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CCC5=CC(=O)CC[C@]45C)C)CC1(CCC(C)CO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	49799581
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO33704	Solanum aphyodendron	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]

☑ 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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2252	Organism	Plasmodium vivax	Plasmodium vivax	Activity	=	39	%	PMID[19299148]

☑ 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 NPC477944 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	247
0.1-0.2	1446
0.2-0.3	5561
0.3-0.4	12106
0.4-0.5	8837
0.5-0.6	6281
0.6-0.7	5119
0.7-0.8	2619
0.8-0.85	398
0.85-0.9	66
0.9-0.95	16
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9439	High Similarity	NPC260665
0.9245	High Similarity	NPC246205
0.9174	High Similarity	NPC477580
0.9159	High Similarity	NPC52241
0.9159	High Similarity	NPC154856
0.9159	High Similarity	NPC475317
0.9143	High Similarity	NPC95243
0.9143	High Similarity	NPC63023
0.9083	High Similarity	NPC178981
0.9048	High Similarity	NPC121566
0.9048	High Similarity	NPC100955
0.9	High Similarity	NPC74727
0.8991	High Similarity	NPC210420
0.8991	High Similarity	NPC474265
0.8991	High Similarity	NPC130427
0.8981	High Similarity	NPC27551
0.8981	High Similarity	NPC114961
0.8947	High Similarity	NPC28532
0.8929	High Similarity	NPC86020
0.8929	High Similarity	NPC475632
0.8909	High Similarity	NPC73455
0.8909	High Similarity	NPC200944
0.886	High Similarity	NPC42675
0.885	High Similarity	NPC161738
0.8829	High Similarity	NPC165439
0.8829	High Similarity	NPC473882
0.8829	High Similarity	NPC474557
0.8796	High Similarity	NPC295389
0.8793	High Similarity	NPC475194
0.8793	High Similarity	NPC277191
0.8793	High Similarity	NPC190846
0.8793	High Similarity	NPC473505
0.8785	High Similarity	NPC162033
0.8783	High Similarity	NPC475431
0.8772	High Similarity	NPC471406
0.8772	High Similarity	NPC475187
0.875	High Similarity	NPC279638
0.8729	High Similarity	NPC69273
0.8729	High Similarity	NPC293623
0.8729	High Similarity	NPC168899
0.8727	High Similarity	NPC285410
0.8727	High Similarity	NPC263827
0.8727	High Similarity	NPC250481
0.8718	High Similarity	NPC174367
0.8718	High Similarity	NPC47113
0.8718	High Similarity	NPC93368
0.8707	High Similarity	NPC238005
0.8707	High Similarity	NPC1980
0.8707	High Similarity	NPC141196
0.8696	High Similarity	NPC182900
0.8696	High Similarity	NPC476545
0.8696	High Similarity	NPC249553
0.8696	High Similarity	NPC476544
0.8696	High Similarity	NPC476543
0.8692	High Similarity	NPC223741
0.8684	High Similarity	NPC319570
0.8661	High Similarity	NPC471398
0.8636	High Similarity	NPC129340
0.8636	High Similarity	NPC101450
0.8636	High Similarity	NPC106760
0.8624	High Similarity	NPC473288
0.8621	High Similarity	NPC15918
0.8621	High Similarity	NPC305771
0.8621	High Similarity	NPC169816
0.8621	High Similarity	NPC94072
0.8621	High Similarity	NPC156789
0.8611	High Similarity	NPC26798
0.8611	High Similarity	NPC210178
0.8596	High Similarity	NPC239293
0.8583	High Similarity	NPC241008
0.8571	High Similarity	NPC56071
0.8571	High Similarity	NPC70733
0.8571	High Similarity	NPC311534
0.8559	High Similarity	NPC198714
0.8559	High Similarity	NPC269466
0.8547	High Similarity	NPC476542
0.8547	High Similarity	NPC160084
0.8547	High Similarity	NPC27363
0.8545	High Similarity	NPC118225
0.8545	High Similarity	NPC8431
0.8545	High Similarity	NPC265655
0.8534	High Similarity	NPC476675
0.8534	High Similarity	NPC475182
0.8532	High Similarity	NPC226642
0.8522	High Similarity	NPC190939
0.8522	High Similarity	NPC197003
0.8505	High Similarity	NPC94919
0.85	High Similarity	NPC471407
0.8491	Intermediate Similarity	NPC167974
0.8487	Intermediate Similarity	NPC329784
0.8487	Intermediate Similarity	NPC152091
0.8487	Intermediate Similarity	NPC240070
0.8482	Intermediate Similarity	NPC477253
0.8482	Intermediate Similarity	NPC471967
0.8476	Intermediate Similarity	NPC187159
0.8475	Intermediate Similarity	NPC473474
0.8462	Intermediate Similarity	NPC216866
0.8462	Intermediate Similarity	NPC108141
0.8455	Intermediate Similarity	NPC195708
0.8455	Intermediate Similarity	NPC258323
0.8455	Intermediate Similarity	NPC224414
0.8455	Intermediate Similarity	NPC295980
0.8448	Intermediate Similarity	NPC470312
0.8448	Intermediate Similarity	NPC308459
0.844	Intermediate Similarity	NPC181845
0.844	Intermediate Similarity	NPC474569
0.8435	Intermediate Similarity	NPC45475
0.843	Intermediate Similarity	NPC173347
0.8421	Intermediate Similarity	NPC244127
0.8421	Intermediate Similarity	NPC31797
0.8407	Intermediate Similarity	NPC102619
0.8407	Intermediate Similarity	NPC251309
0.8407	Intermediate Similarity	NPC62696
0.8407	Intermediate Similarity	NPC293038
0.8403	Intermediate Similarity	NPC469750
0.8403	Intermediate Similarity	NPC250556
0.8393	Intermediate Similarity	NPC292196
0.8393	Intermediate Similarity	NPC274833
0.839	Intermediate Similarity	NPC256983
0.8378	Intermediate Similarity	NPC42482
0.8378	Intermediate Similarity	NPC477069
0.8378	Intermediate Similarity	NPC40440
0.8378	Intermediate Similarity	NPC477070
0.8376	Intermediate Similarity	NPC202051
0.8376	Intermediate Similarity	NPC476672
0.8364	Intermediate Similarity	NPC230507
0.8364	Intermediate Similarity	NPC113044
0.8364	Intermediate Similarity	NPC283829
0.8364	Intermediate Similarity	NPC470432
0.8364	Intermediate Similarity	NPC161676
0.8364	Intermediate Similarity	NPC14704
0.8364	Intermediate Similarity	NPC305423
0.8362	Intermediate Similarity	NPC477071
0.8361	Intermediate Similarity	NPC471855
0.8348	Intermediate Similarity	NPC93883
0.8348	Intermediate Similarity	NPC203862
0.8347	Intermediate Similarity	NPC188234
0.8347	Intermediate Similarity	NPC276838
0.8347	Intermediate Similarity	NPC232785
0.8347	Intermediate Similarity	NPC329986
0.8347	Intermediate Similarity	NPC125077
0.8347	Intermediate Similarity	NPC140092
0.8333	Intermediate Similarity	NPC116024
0.8333	Intermediate Similarity	NPC471356
0.8333	Intermediate Similarity	NPC471357
0.8333	Intermediate Similarity	NPC305496
0.8333	Intermediate Similarity	NPC117702
0.8333	Intermediate Similarity	NPC146456
0.8333	Intermediate Similarity	NPC179412
0.8333	Intermediate Similarity	NPC220293
0.8333	Intermediate Similarity	NPC469757
0.8333	Intermediate Similarity	NPC102088
0.8333	Intermediate Similarity	NPC473928
0.8319	Intermediate Similarity	NPC248202
0.8319	Intermediate Similarity	NPC207845
0.8319	Intermediate Similarity	NPC476674
0.8319	Intermediate Similarity	NPC233003
0.8319	Intermediate Similarity	NPC472719
0.8319	Intermediate Similarity	NPC318135
0.8304	Intermediate Similarity	NPC163314
0.8302	Intermediate Similarity	NPC473890
0.8302	Intermediate Similarity	NPC243728
0.8291	Intermediate Similarity	NPC476670
0.8291	Intermediate Similarity	NPC129393
0.8288	Intermediate Similarity	NPC98696
0.8288	Intermediate Similarity	NPC476538
0.8288	Intermediate Similarity	NPC476541
0.8288	Intermediate Similarity	NPC476539
0.8288	Intermediate Similarity	NPC476540
0.8288	Intermediate Similarity	NPC272576
0.8279	Intermediate Similarity	NPC213634
0.8273	Intermediate Similarity	NPC242748
0.8273	Intermediate Similarity	NPC473476
0.8273	Intermediate Similarity	NPC473923
0.8273	Intermediate Similarity	NPC470309
0.8273	Intermediate Similarity	NPC473199
0.8261	Intermediate Similarity	NPC310341
0.8261	Intermediate Similarity	NPC477031
0.8261	Intermediate Similarity	NPC193382
0.8261	Intermediate Similarity	NPC199428
0.8261	Intermediate Similarity	NPC99620
0.8261	Intermediate Similarity	NPC5311
0.8257	Intermediate Similarity	NPC213190
0.8246	Intermediate Similarity	NPC471627
0.8246	Intermediate Similarity	NPC471173
0.8246	Intermediate Similarity	NPC144068
0.8241	Intermediate Similarity	NPC472023
0.8241	Intermediate Similarity	NPC88000
0.8241	Intermediate Similarity	NPC47566
0.8241	Intermediate Similarity	NPC160734
0.8241	Intermediate Similarity	NPC129372
0.8241	Intermediate Similarity	NPC4831
0.8241	Intermediate Similarity	NPC309425
0.8235	Intermediate Similarity	NPC41129
0.823	Intermediate Similarity	NPC477032
0.823	Intermediate Similarity	NPC124677
0.823	Intermediate Similarity	NPC272242
0.823	Intermediate Similarity	NPC477073
0.823	Intermediate Similarity	NPC197231
0.823	Intermediate Similarity	NPC114188

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 NPC477944 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	1768
0.2-0.3	4226
0.3-0.4	1955
0.4-0.5	489
0.5-0.6	227
0.6-0.7	162
0.7-0.8	103
0.8-0.85	9
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9423	High Similarity	NPD6412	Phase 2
0.8403	Intermediate Similarity	NPD7507	Approved
0.8305	Intermediate Similarity	NPD6370	Approved
0.8264	Intermediate Similarity	NPD7736	Approved
0.8197	Intermediate Similarity	NPD7319	Approved
0.8182	Intermediate Similarity	NPD8293	Discontinued
0.8136	Intermediate Similarity	NPD6054	Approved
0.8136	Intermediate Similarity	NPD6059	Approved
0.8136	Intermediate Similarity	NPD8377	Approved
0.8136	Intermediate Similarity	NPD8294	Approved
0.8125	Intermediate Similarity	NPD6686	Approved
0.812	Intermediate Similarity	NPD7327	Approved
0.812	Intermediate Similarity	NPD7328	Approved
0.8067	Intermediate Similarity	NPD8380	Approved
0.8067	Intermediate Similarity	NPD8378	Approved
0.8067	Intermediate Similarity	NPD8296	Approved
0.8067	Intermediate Similarity	NPD8379	Approved
0.8067	Intermediate Similarity	NPD8335	Approved
0.8067	Intermediate Similarity	NPD8033	Approved
0.8051	Intermediate Similarity	NPD7516	Approved
0.7931	Intermediate Similarity	NPD8133	Approved
0.7917	Intermediate Similarity	NPD7503	Approved
0.7917	Intermediate Similarity	NPD6016	Approved
0.7917	Intermediate Similarity	NPD6015	Approved
0.7895	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD7078	Approved
0.7869	Intermediate Similarity	NPD7492	Approved
0.7851	Intermediate Similarity	NPD5988	Approved
0.7845	Intermediate Similarity	NPD6882	Approved
0.7845	Intermediate Similarity	NPD8297	Approved
0.7807	Intermediate Similarity	NPD7320	Approved
0.7805	Intermediate Similarity	NPD6616	Approved
0.7798	Intermediate Similarity	NPD6083	Phase 2
0.7798	Intermediate Similarity	NPD6084	Phase 2
0.7787	Intermediate Similarity	NPD8328	Phase 3
0.7787	Intermediate Similarity	NPD6067	Discontinued
0.7731	Intermediate Similarity	NPD6009	Approved
0.7699	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD6319	Approved
0.7642	Intermediate Similarity	NPD4753	Phase 2
0.7632	Intermediate Similarity	NPD5739	Approved
0.7632	Intermediate Similarity	NPD7128	Approved
0.7632	Intermediate Similarity	NPD6402	Approved
0.7632	Intermediate Similarity	NPD6675	Approved
0.7627	Intermediate Similarity	NPD4632	Approved
0.7586	Intermediate Similarity	NPD6373	Approved
0.7586	Intermediate Similarity	NPD6372	Approved
0.7547	Intermediate Similarity	NPD6903	Approved
0.754	Intermediate Similarity	NPD6033	Approved
0.75	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD3666	Approved
0.75	Intermediate Similarity	NPD6899	Approved
0.7477	Intermediate Similarity	NPD4755	Approved
0.7458	Intermediate Similarity	NPD8130	Phase 1
0.7458	Intermediate Similarity	NPD6650	Approved
0.7458	Intermediate Similarity	NPD6649	Approved
0.7455	Intermediate Similarity	NPD5695	Phase 3
0.7431	Intermediate Similarity	NPD4202	Approved
0.7422	Intermediate Similarity	NPD5956	Approved
0.7414	Intermediate Similarity	NPD5701	Approved
0.7414	Intermediate Similarity	NPD5697	Approved
0.7411	Intermediate Similarity	NPD5696	Approved
0.7383	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD7290	Approved
0.7373	Intermediate Similarity	NPD4634	Approved
0.7373	Intermediate Similarity	NPD7102	Approved
0.7373	Intermediate Similarity	NPD6883	Approved
0.7358	Intermediate Similarity	NPD6684	Approved
0.7358	Intermediate Similarity	NPD5330	Approved
0.7358	Intermediate Similarity	NPD7521	Approved
0.7358	Intermediate Similarity	NPD7334	Approved
0.7358	Intermediate Similarity	NPD6409	Approved
0.7358	Intermediate Similarity	NPD7146	Approved
0.7345	Intermediate Similarity	NPD5286	Approved
0.7345	Intermediate Similarity	NPD4700	Approved
0.7345	Intermediate Similarity	NPD5285	Approved
0.7345	Intermediate Similarity	NPD4696	Approved
0.7328	Intermediate Similarity	NPD6008	Approved
0.7311	Intermediate Similarity	NPD6869	Approved
0.7311	Intermediate Similarity	NPD6847	Approved
0.7311	Intermediate Similarity	NPD6617	Approved
0.7308	Intermediate Similarity	NPD4221	Approved
0.7308	Intermediate Similarity	NPD4223	Phase 3
0.7297	Intermediate Similarity	NPD4629	Approved
0.7297	Intermediate Similarity	NPD5210	Approved
0.7295	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6014	Approved
0.7288	Intermediate Similarity	NPD6012	Approved
0.7288	Intermediate Similarity	NPD6013	Approved
0.7273	Intermediate Similarity	NPD6399	Phase 3
0.7264	Intermediate Similarity	NPD5329	Approved
0.725	Intermediate Similarity	NPD6053	Discontinued
0.7222	Intermediate Similarity	NPD7604	Phase 2
0.7217	Intermediate Similarity	NPD5224	Approved
0.7217	Intermediate Similarity	NPD5211	Phase 2
0.7217	Intermediate Similarity	NPD5225	Approved
0.7217	Intermediate Similarity	NPD4633	Approved
0.7217	Intermediate Similarity	NPD5226	Approved
0.7203	Intermediate Similarity	NPD6011	Approved
0.72	Intermediate Similarity	NPD5983	Phase 2
0.7179	Intermediate Similarity	NPD4767	Approved
0.7179	Intermediate Similarity	NPD4768	Approved
0.717	Intermediate Similarity	NPD4197	Approved
0.717	Intermediate Similarity	NPD4786	Approved
0.7167	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6673	Approved
0.7156	Intermediate Similarity	NPD5328	Approved
0.7156	Intermediate Similarity	NPD6080	Approved
0.7156	Intermediate Similarity	NPD6904	Approved
0.7155	Intermediate Similarity	NPD5174	Approved
0.7155	Intermediate Similarity	NPD5175	Approved
0.7154	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5223	Approved
0.7117	Intermediate Similarity	NPD8171	Discontinued
0.7109	Intermediate Similarity	NPD6336	Discontinued
0.7105	Intermediate Similarity	NPD7638	Approved
0.7094	Intermediate Similarity	NPD5141	Approved
0.7064	Intermediate Similarity	NPD5737	Approved
0.7064	Intermediate Similarity	NPD6672	Approved
0.7059	Intermediate Similarity	NPD4729	Approved
0.7059	Intermediate Similarity	NPD4730	Approved
0.7054	Intermediate Similarity	NPD7748	Approved
0.7043	Intermediate Similarity	NPD7639	Approved
0.7043	Intermediate Similarity	NPD7640	Approved
0.7037	Intermediate Similarity	NPD3618	Phase 1
0.7037	Intermediate Similarity	NPD4693	Phase 3
0.7037	Intermediate Similarity	NPD4689	Approved
0.7037	Intermediate Similarity	NPD4138	Approved
0.7037	Intermediate Similarity	NPD4690	Approved
0.7037	Intermediate Similarity	NPD4688	Approved
0.7037	Intermediate Similarity	NPD5205	Approved
0.7027	Intermediate Similarity	NPD6079	Approved
0.7027	Intermediate Similarity	NPD5281	Approved
0.7027	Intermediate Similarity	NPD5284	Approved
0.7018	Intermediate Similarity	NPD7902	Approved
0.7009	Intermediate Similarity	NPD4754	Approved
0.7	Intermediate Similarity	NPD8336	Approved
0.7	Intermediate Similarity	NPD8337	Approved
0.6981	Remote Similarity	NPD3667	Approved
0.6942	Remote Similarity	NPD5250	Approved
0.6942	Remote Similarity	NPD5251	Approved
0.6942	Remote Similarity	NPD5249	Phase 3
0.6942	Remote Similarity	NPD5247	Approved
0.6942	Remote Similarity	NPD5248	Approved
0.6935	Remote Similarity	NPD6274	Approved
0.6917	Remote Similarity	NPD5128	Approved
0.6917	Remote Similarity	NPD8449	Approved
0.6916	Remote Similarity	NPD4788	Approved
0.6909	Remote Similarity	NPD5208	Approved
0.6905	Remote Similarity	NPD7100	Approved
0.6905	Remote Similarity	NPD4522	Approved
0.6905	Remote Similarity	NPD7101	Approved
0.6881	Remote Similarity	NPD4694	Approved
0.6881	Remote Similarity	NPD5280	Approved
0.6881	Remote Similarity	NPD5690	Phase 2
0.6881	Remote Similarity	NPD5279	Phase 3
0.6881	Remote Similarity	NPD6098	Approved
0.6875	Remote Similarity	NPD5693	Phase 1
0.6875	Remote Similarity	NPD6050	Approved
0.6875	Remote Similarity	NPD7515	Phase 2
0.6866	Remote Similarity	NPD8450	Suspended
0.686	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6335	Approved
0.6797	Remote Similarity	NPD8517	Approved
0.6797	Remote Similarity	NPD8515	Approved
0.6797	Remote Similarity	NPD8513	Phase 3
0.6797	Remote Similarity	NPD6908	Approved
0.6797	Remote Similarity	NPD8516	Approved
0.6797	Remote Similarity	NPD6909	Approved
0.6786	Remote Similarity	NPD5692	Phase 3
0.6786	Remote Similarity	NPD5207	Approved
0.6783	Remote Similarity	NPD5222	Approved
0.6783	Remote Similarity	NPD4697	Phase 3
0.6783	Remote Similarity	NPD5221	Approved
0.6783	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6001	Approved
0.6754	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7900	Approved
0.6748	Remote Similarity	NPD5216	Approved
0.6748	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5215	Approved
0.6748	Remote Similarity	NPD5217	Approved
0.6746	Remote Similarity	NPD6317	Approved
0.6727	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD8034	Phase 2
0.6726	Remote Similarity	NPD5694	Approved
0.6726	Remote Similarity	NPD8035	Phase 2
0.6724	Remote Similarity	NPD5173	Approved
0.6698	Remote Similarity	NPD4195	Approved
0.6694	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD6313	Approved
0.6693	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD7524	Approved
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)

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