NPASS Compound

Structure

NPC476427 OpenBabel07101718232D 24 27 0 0 1 0 0 0 0 0999 V2000 2.5765 -1.7735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1282 -0.1004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4096 2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7701 0.9809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7250 0.2989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0375 1.1748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6991 1.4020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6674 1.0676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0881 -0.1353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0375 -1.8252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8286 -1.3252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9035 -0.3252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8694 -1.0664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0375 0.1748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3360 0.9678 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4068 2.3030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9729 1.4020 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3936 0.1991 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9035 -1.3252 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8286 -0.3252 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8435 3.1292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4040 2.3777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7708 -0.4450 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 4 18 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 14 20 1 0 0 0 0 15 17 1 6 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 3 1 6 0 0 0 18 20 1 1 0 0 0 19 13 1 1 0 0 0 19 23 1 0 0 0 0 20 11 1 6 0 0 0 20 24 1 0 0 0 0 23 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	350.138
LogP:	3.873
LogD:	2.781
LogS:	-4.628
# Rotatable Bonds:	2
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.597
Synthetic Accessibility Score:	6.087
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.212
MDCK Permeability:	2.3747608793200925e-05
Pgp-inhibitor:	0.026
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	94.59973907470703%
Volume Distribution (VD):	0.589
Pgp-substrate:	3.3506758213043213%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.941
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.92
CYP2C9-inhibitor:	0.151
CYP2C9-substrate:	0.325
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.183
CYP3A4-substrate:	0.859

ADMET: Excretion

Clearance (CL):	1.345
Half-life (T1/2):	0.488

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.312
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.234
Skin Sensitization:	0.496
Carcinogencity:	0.711
Eye Corrosion:	0.254
Eye Irritation:	0.753
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC476427

Natural Product ID:	NPC476427
*Common Name:**	OOHFJWCHEFCJDC-AXDKOMKPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OOHFJWCHEFCJDC-AXDKOMKPSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-13(2)19-10-11-20(24-23-19)14(12-19)6-7-15-17(3,16(21)22)8-5-9-18(15,20)4/h12-13,15H,5-11H2,1-4H3,(H,21,22)/t15-,17+,18-,19-,20+/m0/s1
SMILES:	CC([C@@]12CC[C@@]3(OO1)C(=C2)CC[C@@H]1[C@]3(C)CCC[C@@]1(C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL602107
PubChem CID:	46230361
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000368] Dioxanes [CHEMONTID:0001312] 1,2-dioxanes

*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
NPO2882	Abies georgei	Species	Pinaceae	Eukaryota	aerial parts	Zhongdian city, Yunnan Province of China	n.a.	PMID[20022253]

☑ 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	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100.0	ug.mL-1	PMID[534658]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[534658]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	52400.0	nM	PMID[534659]
NPT2	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[534658]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[534658]

☑ 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 NPC476427 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	212
0.1-0.2	1375
0.2-0.3	4931
0.3-0.4	12826
0.4-0.5	10559
0.5-0.6	6264
0.6-0.7	5221
0.7-0.8	1219
0.8-0.85	78
0.85-0.9	2
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475101
1.0	High Similarity	NPC124927
0.9756	High Similarity	NPC470415
0.9111	High Similarity	NPC472851
0.8523	High Similarity	NPC231599
0.8478	Intermediate Similarity	NPC266899
0.8352	Intermediate Similarity	NPC476417
0.8172	Intermediate Similarity	NPC470958
0.8172	Intermediate Similarity	NPC470957
0.814	Intermediate Similarity	NPC37038
0.8105	Intermediate Similarity	NPC189880
0.8085	Intermediate Similarity	NPC473240
0.8046	Intermediate Similarity	NPC221647
0.8023	Intermediate Similarity	NPC231431
0.8022	Intermediate Similarity	NPC48107
0.8	Intermediate Similarity	NPC61952
0.8	Intermediate Similarity	NPC239685
0.8	Intermediate Similarity	NPC476318
0.8	Intermediate Similarity	NPC476327
0.7917	Intermediate Similarity	NPC170131
0.7912	Intermediate Similarity	NPC476932
0.7912	Intermediate Similarity	NPC476409
0.7907	Intermediate Similarity	NPC280654
0.7907	Intermediate Similarity	NPC198240
0.7907	Intermediate Similarity	NPC110094
0.7907	Intermediate Similarity	NPC260385
0.7889	Intermediate Similarity	NPC471344
0.7872	Intermediate Similarity	NPC131840
0.7865	Intermediate Similarity	NPC107253
0.7857	Intermediate Similarity	NPC103958
0.7857	Intermediate Similarity	NPC183503
0.7857	Intermediate Similarity	NPC161923
0.7857	Intermediate Similarity	NPC283908
0.7841	Intermediate Similarity	NPC226068
0.7841	Intermediate Similarity	NPC142244
0.7835	Intermediate Similarity	NPC58942
0.7835	Intermediate Similarity	NPC260149
0.7822	Intermediate Similarity	NPC64844
0.7822	Intermediate Similarity	NPC42847
0.7816	Intermediate Similarity	NPC199595
0.7812	Intermediate Similarity	NPC235053
0.7812	Intermediate Similarity	NPC29952
0.7802	Intermediate Similarity	NPC73038
0.7802	Intermediate Similarity	NPC473226
0.7802	Intermediate Similarity	NPC262085
0.7802	Intermediate Similarity	NPC82979
0.7802	Intermediate Similarity	NPC476104
0.7791	Intermediate Similarity	NPC165711
0.7791	Intermediate Similarity	NPC471897
0.7791	Intermediate Similarity	NPC107039
0.7791	Intermediate Similarity	NPC471899
0.7789	Intermediate Similarity	NPC474963
0.7778	Intermediate Similarity	NPC162973
0.7778	Intermediate Similarity	NPC156981
0.7765	Intermediate Similarity	NPC279666
0.7765	Intermediate Similarity	NPC192540
0.7755	Intermediate Similarity	NPC471041
0.7755	Intermediate Similarity	NPC471413
0.7742	Intermediate Similarity	NPC64872
0.7742	Intermediate Similarity	NPC471342
0.7742	Intermediate Similarity	NPC25906
0.7742	Intermediate Similarity	NPC290972
0.7742	Intermediate Similarity	NPC469866
0.7732	Intermediate Similarity	NPC473456
0.7727	Intermediate Similarity	NPC104545
0.7717	Intermediate Similarity	NPC30421
0.7708	Intermediate Similarity	NPC134067
0.7708	Intermediate Similarity	NPC272617
0.7708	Intermediate Similarity	NPC139570
0.7708	Intermediate Similarity	NPC290481
0.7708	Intermediate Similarity	NPC53565
0.7701	Intermediate Similarity	NPC179028
0.7701	Intermediate Similarity	NPC321514
0.7701	Intermediate Similarity	NPC239098
0.77	Intermediate Similarity	NPC90177
0.7692	Intermediate Similarity	NPC269638
0.7692	Intermediate Similarity	NPC224345
0.7684	Intermediate Similarity	NPC118490
0.7684	Intermediate Similarity	NPC158059
0.7684	Intermediate Similarity	NPC476416
0.7684	Intermediate Similarity	NPC202728
0.7684	Intermediate Similarity	NPC477855
0.7684	Intermediate Similarity	NPC118519
0.7677	Intermediate Similarity	NPC471412
0.7674	Intermediate Similarity	NPC89294
0.7674	Intermediate Similarity	NPC69143
0.767	Intermediate Similarity	NPC143706
0.767	Intermediate Similarity	NPC472534
0.766	Intermediate Similarity	NPC120968
0.766	Intermediate Similarity	NPC214844
0.766	Intermediate Similarity	NPC273621
0.766	Intermediate Similarity	NPC232202
0.766	Intermediate Similarity	NPC227467
0.766	Intermediate Similarity	NPC210037
0.766	Intermediate Similarity	NPC130278
0.766	Intermediate Similarity	NPC290614
0.766	Intermediate Similarity	NPC193750
0.766	Intermediate Similarity	NPC18872
0.766	Intermediate Similarity	NPC476369
0.766	Intermediate Similarity	NPC7260
0.766	Intermediate Similarity	NPC477872
0.766	Intermediate Similarity	NPC476437
0.7647	Intermediate Similarity	NPC3753
0.7647	Intermediate Similarity	NPC46610
0.7647	Intermediate Similarity	NPC241854
0.7647	Intermediate Similarity	NPC476046
0.7647	Intermediate Similarity	NPC237591
0.7647	Intermediate Similarity	NPC18819
0.7647	Intermediate Similarity	NPC251970
0.764	Intermediate Similarity	NPC40228
0.764	Intermediate Similarity	NPC162632
0.764	Intermediate Similarity	NPC274050
0.764	Intermediate Similarity	NPC471898
0.764	Intermediate Similarity	NPC263272
0.764	Intermediate Similarity	NPC229584
0.764	Intermediate Similarity	NPC267691
0.764	Intermediate Similarity	NPC14203
0.764	Intermediate Similarity	NPC278459
0.7634	Intermediate Similarity	NPC104560
0.7634	Intermediate Similarity	NPC50847
0.7634	Intermediate Similarity	NPC52169
0.7634	Intermediate Similarity	NPC182797
0.7629	Intermediate Similarity	NPC116457
0.7629	Intermediate Similarity	NPC477853
0.7629	Intermediate Similarity	NPC307282
0.7629	Intermediate Similarity	NPC305464
0.7629	Intermediate Similarity	NPC19376
0.7629	Intermediate Similarity	NPC25848
0.7624	Intermediate Similarity	NPC475036
0.7624	Intermediate Similarity	NPC474281
0.7614	Intermediate Similarity	NPC16394
0.7609	Intermediate Similarity	NPC324063
0.7609	Intermediate Similarity	NPC472986
0.7609	Intermediate Similarity	NPC472869
0.7609	Intermediate Similarity	NPC472985
0.7609	Intermediate Similarity	NPC322159
0.7604	Intermediate Similarity	NPC474529
0.7604	Intermediate Similarity	NPC114159
0.7604	Intermediate Similarity	NPC159365
0.7604	Intermediate Similarity	NPC148964
0.7604	Intermediate Similarity	NPC191412
0.7604	Intermediate Similarity	NPC91010
0.7604	Intermediate Similarity	NPC476415
0.7604	Intermediate Similarity	NPC6818
0.7586	Intermediate Similarity	NPC132542
0.7582	Intermediate Similarity	NPC251170
0.7582	Intermediate Similarity	NPC96095
0.7582	Intermediate Similarity	NPC248758
0.7579	Intermediate Similarity	NPC472978
0.7579	Intermediate Similarity	NPC105189
0.7579	Intermediate Similarity	NPC38754
0.7579	Intermediate Similarity	NPC187722
0.7579	Intermediate Similarity	NPC475708
0.7576	Intermediate Similarity	NPC471727
0.7576	Intermediate Similarity	NPC472972
0.7576	Intermediate Similarity	NPC470074
0.7573	Intermediate Similarity	NPC189075
0.7573	Intermediate Similarity	NPC275539
0.7558	Intermediate Similarity	NPC39362
0.7558	Intermediate Similarity	NPC476844
0.7556	Intermediate Similarity	NPC302661
0.7556	Intermediate Similarity	NPC476292
0.7556	Intermediate Similarity	NPC474605
0.7556	Intermediate Similarity	NPC251779
0.7556	Intermediate Similarity	NPC238991
0.7556	Intermediate Similarity	NPC69101
0.7553	Intermediate Similarity	NPC472973
0.7553	Intermediate Similarity	NPC61543
0.7553	Intermediate Similarity	NPC59263
0.7553	Intermediate Similarity	NPC270768
0.7553	Intermediate Similarity	NPC281524
0.7553	Intermediate Similarity	NPC234346
0.7553	Intermediate Similarity	NPC127689
0.7553	Intermediate Similarity	NPC225585
0.7553	Intermediate Similarity	NPC293048
0.7553	Intermediate Similarity	NPC130520
0.7553	Intermediate Similarity	NPC121798
0.7553	Intermediate Similarity	NPC263393
0.7553	Intermediate Similarity	NPC274330
0.7553	Intermediate Similarity	NPC143232
0.7553	Intermediate Similarity	NPC198664
0.7551	Intermediate Similarity	NPC285513
0.7551	Intermediate Similarity	NPC254496
0.7551	Intermediate Similarity	NPC43686
0.7549	Intermediate Similarity	NPC478208
0.7549	Intermediate Similarity	NPC469607
0.7528	Intermediate Similarity	NPC477057
0.7527	Intermediate Similarity	NPC293564
0.7527	Intermediate Similarity	NPC307426
0.7527	Intermediate Similarity	NPC18064
0.7527	Intermediate Similarity	NPC102683
0.7527	Intermediate Similarity	NPC298904
0.7527	Intermediate Similarity	NPC68160
0.7527	Intermediate Similarity	NPC130577
0.7527	Intermediate Similarity	NPC171203
0.7527	Intermediate Similarity	NPC98442
0.7527	Intermediate Similarity	NPC128644
0.7527	Intermediate Similarity	NPC471728
0.7527	Intermediate Similarity	NPC242468
0.7527	Intermediate Similarity	NPC471792

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 NPC476427 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	1699
0.2-0.3	3854
0.3-0.4	2274
0.4-0.5	682
0.5-0.6	208
0.6-0.7	211
0.7-0.8	12
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7717	Intermediate Similarity	NPD3573	Approved
0.7396	Intermediate Similarity	NPD7515	Phase 2
0.7245	Intermediate Similarity	NPD7748	Approved
0.72	Intermediate Similarity	NPD7902	Approved
0.7143	Intermediate Similarity	NPD4695	Discontinued
0.7129	Intermediate Similarity	NPD7638	Approved
0.7059	Intermediate Similarity	NPD7640	Approved
0.7059	Intermediate Similarity	NPD7639	Approved
0.7053	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4519	Discontinued
0.7053	Intermediate Similarity	NPD4623	Approved
0.7048	Intermediate Similarity	NPD6675	Approved
0.7048	Intermediate Similarity	NPD6402	Approved
0.7048	Intermediate Similarity	NPD7128	Approved
0.7048	Intermediate Similarity	NPD5739	Approved
0.7041	Intermediate Similarity	NPD6411	Approved
0.7041	Intermediate Similarity	NPD5284	Approved
0.7041	Intermediate Similarity	NPD5281	Approved
0.703	Intermediate Similarity	NPD4755	Approved
0.701	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5328	Approved
0.6989	Remote Similarity	NPD4223	Phase 3
0.6989	Remote Similarity	NPD4221	Approved
0.6989	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5697	Approved
0.6981	Remote Similarity	NPD5701	Approved
0.697	Remote Similarity	NPD6399	Phase 3
0.697	Remote Similarity	NPD5779	Approved
0.697	Remote Similarity	NPD5778	Approved
0.6947	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5211	Phase 2
0.6916	Remote Similarity	NPD6011	Approved
0.6916	Remote Similarity	NPD7320	Approved
0.6916	Remote Similarity	NPD6881	Approved
0.6916	Remote Similarity	NPD6899	Approved
0.6916	Remote Similarity	NPD6686	Approved
0.6909	Remote Similarity	NPD4632	Approved
0.69	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7900	Approved
0.6893	Remote Similarity	NPD5286	Approved
0.6893	Remote Similarity	NPD5285	Approved
0.6893	Remote Similarity	NPD4700	Approved
0.6893	Remote Similarity	NPD4696	Approved
0.6887	Remote Similarity	NPD6008	Approved
0.6875	Remote Similarity	NPD3618	Phase 1
0.6869	Remote Similarity	NPD6079	Approved
0.6869	Remote Similarity	NPD8034	Phase 2
0.6869	Remote Similarity	NPD8035	Phase 2
0.6852	Remote Similarity	NPD6373	Approved
0.6852	Remote Similarity	NPD6372	Approved
0.6852	Remote Similarity	NPD6014	Approved
0.6852	Remote Similarity	NPD6012	Approved
0.6852	Remote Similarity	NPD6013	Approved
0.6842	Remote Similarity	NPD4197	Approved
0.6838	Remote Similarity	NPD7507	Approved
0.6837	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6101	Approved
0.6827	Remote Similarity	NPD5223	Approved
0.6809	Remote Similarity	NPD3667	Approved
0.68	Remote Similarity	NPD4202	Approved
0.6792	Remote Similarity	NPD5141	Approved
0.6789	Remote Similarity	NPD7102	Approved
0.6789	Remote Similarity	NPD7290	Approved
0.6789	Remote Similarity	NPD6883	Approved
0.6771	Remote Similarity	NPD5329	Approved
0.6765	Remote Similarity	NPD4697	Phase 3
0.6765	Remote Similarity	NPD5221	Approved
0.6765	Remote Similarity	NPD7614	Phase 1
0.6765	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5222	Approved
0.6762	Remote Similarity	NPD5225	Approved
0.6762	Remote Similarity	NPD5224	Approved
0.6762	Remote Similarity	NPD4633	Approved
0.6762	Remote Similarity	NPD5226	Approved
0.6759	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD8130	Phase 1
0.6727	Remote Similarity	NPD6869	Approved
0.6727	Remote Similarity	NPD6649	Approved
0.6727	Remote Similarity	NPD6847	Approved
0.6727	Remote Similarity	NPD6617	Approved
0.6727	Remote Similarity	NPD6650	Approved
0.6727	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6009	Approved
0.6701	Remote Similarity	NPD6098	Approved
0.6701	Remote Similarity	NPD4693	Phase 3
0.6701	Remote Similarity	NPD4138	Approved
0.6701	Remote Similarity	NPD4688	Approved
0.6701	Remote Similarity	NPD4690	Approved
0.6701	Remote Similarity	NPD4689	Approved
0.6701	Remote Similarity	NPD5205	Approved
0.67	Remote Similarity	NPD5693	Phase 1
0.6699	Remote Similarity	NPD6083	Phase 2
0.6699	Remote Similarity	NPD6084	Phase 2
0.6699	Remote Similarity	NPD5173	Approved
0.6698	Remote Similarity	NPD5174	Approved
0.6698	Remote Similarity	NPD4754	Approved
0.6698	Remote Similarity	NPD5175	Approved
0.6697	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.6636	Remote Similarity	NPD4634	Approved
0.6636	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5696	Approved
0.6596	Remote Similarity	NPD7525	Registered
0.6579	Remote Similarity	NPD7115	Discovery
0.6574	Remote Similarity	NPD4767	Approved
0.6574	Remote Similarity	NPD4768	Approved
0.6569	Remote Similarity	NPD6001	Approved
0.6566	Remote Similarity	NPD6672	Approved
0.6566	Remote Similarity	NPD5737	Approved
0.6566	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5208	Approved
0.6559	Remote Similarity	NPD3617	Approved
0.6552	Remote Similarity	NPD6319	Approved
0.6545	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5690	Phase 2
0.6531	Remote Similarity	NPD5280	Approved
0.6531	Remote Similarity	NPD7334	Approved
0.6531	Remote Similarity	NPD7521	Approved
0.6531	Remote Similarity	NPD4694	Approved
0.6531	Remote Similarity	NPD6684	Approved
0.6531	Remote Similarity	NPD6409	Approved
0.6531	Remote Similarity	NPD7146	Approved
0.6531	Remote Similarity	NPD5330	Approved
0.6525	Remote Similarity	NPD8328	Phase 3
0.6518	Remote Similarity	NPD6053	Discontinued
0.6514	Remote Similarity	NPD6412	Phase 2
0.6496	Remote Similarity	NPD5983	Phase 2
0.6495	Remote Similarity	NPD3668	Phase 3
0.6491	Remote Similarity	NPD6274	Approved
0.6476	Remote Similarity	NPD4225	Approved
0.6455	Remote Similarity	NPD4730	Approved
0.6455	Remote Similarity	NPD5128	Approved
0.6455	Remote Similarity	NPD4729	Approved
0.6449	Remote Similarity	NPD7632	Discontinued
0.6437	Remote Similarity	NPD7331	Phase 2
0.6436	Remote Similarity	NPD5692	Phase 3
0.6435	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6317	Approved
0.64	Remote Similarity	NPD6903	Approved
0.6387	Remote Similarity	NPD7604	Phase 2
0.6383	Remote Similarity	NPD6115	Approved
0.6383	Remote Similarity	NPD6118	Approved
0.6383	Remote Similarity	NPD6697	Approved
0.6383	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6114	Approved
0.6379	Remote Similarity	NPD6335	Approved
0.6379	Remote Similarity	NPD6313	Approved
0.6379	Remote Similarity	NPD6314	Approved
0.6373	Remote Similarity	NPD5694	Approved
0.6373	Remote Similarity	NPD6050	Approved
0.6373	Remote Similarity	NPD7637	Suspended
0.6364	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5279	Phase 3
0.6354	Remote Similarity	NPD4139	Approved
0.6354	Remote Similarity	NPD4692	Approved
0.6346	Remote Similarity	NPD4629	Approved
0.6346	Remote Similarity	NPD5210	Approved
0.6339	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5249	Phase 3
0.6339	Remote Similarity	NPD5169	Approved
0.6339	Remote Similarity	NPD5247	Approved
0.6339	Remote Similarity	NPD5135	Approved
0.6339	Remote Similarity	NPD5251	Approved
0.6339	Remote Similarity	NPD5250	Approved
0.6339	Remote Similarity	NPD5248	Approved
0.6333	Remote Similarity	NPD7492	Approved
0.6325	Remote Similarity	NPD7101	Approved
0.6325	Remote Similarity	NPD7100	Approved
0.6322	Remote Similarity	NPD7341	Phase 2
0.6316	Remote Similarity	NPD4195	Approved
0.6316	Remote Similarity	NPD7645	Phase 2
0.6316	Remote Similarity	NPD8133	Approved
0.6311	Remote Similarity	NPD7736	Approved
0.6286	Remote Similarity	NPD7732	Phase 3
0.6283	Remote Similarity	NPD5217	Approved
0.6283	Remote Similarity	NPD5215	Approved
0.6283	Remote Similarity	NPD5216	Approved
0.6283	Remote Similarity	NPD5127	Approved
0.6281	Remote Similarity	NPD6336	Discontinued
0.6281	Remote Similarity	NPD6616	Approved
0.6277	Remote Similarity	NPD6116	Phase 1
0.6275	Remote Similarity	NPD4096	Approved
0.6275	Remote Similarity	NPD46	Approved
0.6275	Remote Similarity	NPD5207	Approved
0.6275	Remote Similarity	NPD6698	Approved
0.6271	Remote Similarity	NPD6059	Approved
0.6271	Remote Similarity	NPD6054	Approved
0.6264	Remote Similarity	NPD4243	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