NPASS Compound

Structure

NPC201370 OpenBabel07101718202D 28 29 0 0 1 0 0 0 0 0999 V2000 -0.1829 -3.6551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3171 -6.2532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3171 -4.5211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3171 -1.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -3.6551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3171 -1.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3171 -2.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3171 -4.5211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1829 -1.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3171 -1.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8171 -5.3871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3171 -2.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -5.3871 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8171 -5.3871 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3171 -6.2532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3171 -6.2532 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8171 -5.3871 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.8171 -7.1192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8171 -7.1192 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 17 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 13 2 0 0 0 0 7 11 1 0 0 0 0 7 14 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 17 2 0 0 0 0 11 20 1 0 0 0 0 12 15 2 0 0 0 0 12 20 1 0 0 0 0 13 24 1 0 0 0 0 14 24 1 0 0 0 0 15 28 1 0 0 0 0 16 18 1 0 0 0 0 16 21 1 0 0 0 0 18 2 1 1 0 0 0 19 3 1 6 0 0 0 19 22 1 0 0 0 0 19 25 1 0 0 0 0 20 23 2 0 0 0 0 21 22 1 0 0 0 0 21 26 2 0 0 0 0 22 27 1 1 0 0 0 23 24 1 0 0 0 0 23 28 1 0 0 0 0 24 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.23
Volume:	434.947
LogP:	5.284
LogD:	4.837
LogS:	-4.961
# Rotatable Bonds:	10
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.375
Synthetic Accessibility Score:	4.704
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.594
MDCK Permeability:	2.5226827347069047e-05
Pgp-inhibitor:	0.129
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.066

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.675
Plasma Protein Binding (PPB):	96.52729034423828%
Volume Distribution (VD):	1.666
Pgp-substrate:	2.556676149368286%

ADMET: Metabolism

CYP1A2-inhibitor:	0.572
CYP1A2-substrate:	0.576
CYP2C19-inhibitor:	0.736
CYP2C19-substrate:	0.865
CYP2C9-inhibitor:	0.892
CYP2C9-substrate:	0.799
CYP2D6-inhibitor:	0.892
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.948
CYP3A4-substrate:	0.457

ADMET: Excretion

Clearance (CL):	12.124
Half-life (T1/2):	0.171

ADMET: Toxicity

hERG Blockers:	0.166
Human Hepatotoxicity (H-HT):	0.945
Drug-inuced Liver Injury (DILI):	0.298
AMES Toxicity:	0.194
Rat Oral Acute Toxicity:	0.952
Maximum Recommended Daily Dose:	0.901
Skin Sensitization:	0.183
Carcinogencity:	0.947
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC201370

Natural Product ID:	NPC201370
*Common Name:**	(6S,10Z,12E)-2-Chloro-3-Hydroxy-6,10-Dimethyl-13-((S)-7-Methyl-4,5,6,7-Tetrahydrobenzofuran-7-Yl)Trideca-10,12-Dien-4-One
IUPAC Name:	(2S,3S,6S,10Z,12E)-2-chloro-3-hydroxy-6,10-dimethyl-13-[(7S)-7-methyl-5,6-dihydro-4H-1-benzofuran-7-yl]trideca-10,12-dien-4-one
Synonyms:
Standard InCHIKey:	IGLKUNSGZGFDPG-SDBOTNDTSA-N
Standard InCHI:	InChI=1S/C24H35ClO3/c1-17(8-5-9-18(2)16-21(26)22(27)19(3)25)10-6-13-24(4)14-7-11-20-12-15-28-23(20)24/h6,10,12-13,15,18-19,22,27H,5,7-9,11,14,16H2,1-4H3/b13-6+,17-10-/t18-,19-,22+,24+/m0/s1
SMILES:	C[C@H](CC(=O)[C@@H]([C@@H](Cl)C)O)CCC/C(=CC=C[C@]1(C)CCCc2c1occ2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL514888
PubChem CID:	10982396
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO32608	ircinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277743]
NPO32608	ircinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908961]
NPO32608	ircinia sp.	Species	Irciniidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[12608859]
NPO32608	ircinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18163586]
NPO32608	ircinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7769397]
NPO32608	ircinia sp.	Species	Irciniidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[7853011]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	<	1.0	ug.mL-1	PMID[490525]

☑ 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 NPC201370 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	283
0.1-0.2	1429
0.2-0.3	3484
0.3-0.4	9916
0.4-0.5	10759
0.5-0.6	8561
0.6-0.7	7686
0.7-0.8	546
0.8-0.85	30
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473983
0.9394	High Similarity	NPC473982
0.8529	High Similarity	NPC329707
0.838	Intermediate Similarity	NPC170604
0.838	Intermediate Similarity	NPC215109
0.837	Intermediate Similarity	NPC118853
0.8321	Intermediate Similarity	NPC246392
0.8264	Intermediate Similarity	NPC202260
0.8261	Intermediate Similarity	NPC26532
0.8222	Intermediate Similarity	NPC477967
0.8214	Intermediate Similarity	NPC61788
0.8201	Intermediate Similarity	NPC59502
0.8194	Intermediate Similarity	NPC472376
0.8188	Intermediate Similarity	NPC290955
0.8175	Intermediate Similarity	NPC473885
0.8175	Intermediate Similarity	NPC471074
0.8148	Intermediate Similarity	NPC97566
0.8116	Intermediate Similarity	NPC23086
0.8112	Intermediate Similarity	NPC476947
0.8099	Intermediate Similarity	NPC218838
0.8095	Intermediate Similarity	NPC263337
0.806	Intermediate Similarity	NPC243704
0.8058	Intermediate Similarity	NPC474830
0.8043	Intermediate Similarity	NPC290193
0.8043	Intermediate Similarity	NPC474829
0.8	Intermediate Similarity	NPC307401
0.8	Intermediate Similarity	NPC64157
0.8	Intermediate Similarity	NPC473268
0.8	Intermediate Similarity	NPC278832
0.8	Intermediate Similarity	NPC279877
0.7986	Intermediate Similarity	NPC46536
0.7986	Intermediate Similarity	NPC138139
0.7985	Intermediate Similarity	NPC217180
0.7985	Intermediate Similarity	NPC312525
0.797	Intermediate Similarity	NPC205523
0.7959	Intermediate Similarity	NPC148374
0.7958	Intermediate Similarity	NPC89133
0.7922	Intermediate Similarity	NPC121615
0.7922	Intermediate Similarity	NPC294511
0.7919	Intermediate Similarity	NPC243577
0.7917	Intermediate Similarity	NPC106247
0.7914	Intermediate Similarity	NPC300098
0.7908	Intermediate Similarity	NPC212257
0.7902	Intermediate Similarity	NPC471817
0.7895	Intermediate Similarity	NPC93666
0.7887	Intermediate Similarity	NPC939
0.7872	Intermediate Similarity	NPC112706
0.7872	Intermediate Similarity	NPC207294
0.7871	Intermediate Similarity	NPC282793
0.7862	Intermediate Similarity	NPC265793
0.7857	Intermediate Similarity	NPC470858
0.7852	Intermediate Similarity	NPC208906
0.7852	Intermediate Similarity	NPC144745
0.7847	Intermediate Similarity	NPC293253
0.7842	Intermediate Similarity	NPC243269
0.7842	Intermediate Similarity	NPC178382
0.7838	Intermediate Similarity	NPC67003
0.7836	Intermediate Similarity	NPC150895
0.7832	Intermediate Similarity	NPC477645
0.7821	Intermediate Similarity	NPC469966
0.7817	Intermediate Similarity	NPC208389
0.7808	Intermediate Similarity	NPC303217
0.7808	Intermediate Similarity	NPC46896
0.7806	Intermediate Similarity	NPC246164
0.7801	Intermediate Similarity	NPC83178
0.7794	Intermediate Similarity	NPC187547
0.7794	Intermediate Similarity	NPC21831
0.7785	Intermediate Similarity	NPC116639
0.7778	Intermediate Similarity	NPC474987
0.7778	Intermediate Similarity	NPC59035
0.7778	Intermediate Similarity	NPC79202
0.777	Intermediate Similarity	NPC16922
0.7754	Intermediate Similarity	NPC79557
0.7746	Intermediate Similarity	NPC477966
0.7746	Intermediate Similarity	NPC477123
0.7746	Intermediate Similarity	NPC477040
0.774	Intermediate Similarity	NPC158525
0.7733	Intermediate Similarity	NPC52412
0.773	Intermediate Similarity	NPC329694
0.773	Intermediate Similarity	NPC474260
0.773	Intermediate Similarity	NPC81912
0.773	Intermediate Similarity	NPC329922
0.7722	Intermediate Similarity	NPC194499
0.7714	Intermediate Similarity	NPC477965
0.7714	Intermediate Similarity	NPC477038
0.7714	Intermediate Similarity	NPC188377
0.7714	Intermediate Similarity	NPC141252
0.7714	Intermediate Similarity	NPC11799
0.7714	Intermediate Similarity	NPC65735
0.7712	Intermediate Similarity	NPC71821
0.7703	Intermediate Similarity	NPC130976
0.7703	Intermediate Similarity	NPC177262
0.7698	Intermediate Similarity	NPC471549
0.7698	Intermediate Similarity	NPC473379
0.7698	Intermediate Similarity	NPC263870
0.7698	Intermediate Similarity	NPC317217
0.7697	Intermediate Similarity	NPC185456
0.7697	Intermediate Similarity	NPC56731
0.7682	Intermediate Similarity	NPC476946
0.7677	Intermediate Similarity	NPC228842
0.7676	Intermediate Similarity	NPC476016
0.7673	Intermediate Similarity	NPC474611
0.7673	Intermediate Similarity	NPC472823
0.7667	Intermediate Similarity	NPC205765
0.7667	Intermediate Similarity	NPC477537
0.7667	Intermediate Similarity	NPC477535
0.7664	Intermediate Similarity	NPC87466
0.7664	Intermediate Similarity	NPC206007
0.766	Intermediate Similarity	NPC303010
0.766	Intermediate Similarity	NPC179354
0.7658	Intermediate Similarity	NPC41880
0.7655	Intermediate Similarity	NPC15083
0.7655	Intermediate Similarity	NPC196979
0.7655	Intermediate Similarity	NPC470976
0.7655	Intermediate Similarity	NPC471995
0.7655	Intermediate Similarity	NPC470977
0.7651	Intermediate Similarity	NPC90953
0.7651	Intermediate Similarity	NPC107571
0.7643	Intermediate Similarity	NPC272899
0.7643	Intermediate Similarity	NPC44606
0.7639	Intermediate Similarity	NPC476925
0.7632	Intermediate Similarity	NPC158871
0.7622	Intermediate Similarity	NPC474438
0.7622	Intermediate Similarity	NPC327527
0.7622	Intermediate Similarity	NPC477039
0.7622	Intermediate Similarity	NPC476917
0.7622	Intermediate Similarity	NPC474279
0.7619	Intermediate Similarity	NPC477210
0.7619	Intermediate Similarity	NPC209858
0.7616	Intermediate Similarity	NPC121158
0.761	Intermediate Similarity	NPC7059
0.761	Intermediate Similarity	NPC195954
0.761	Intermediate Similarity	NPC88007
0.761	Intermediate Similarity	NPC304692
0.7609	Intermediate Similarity	NPC473969
0.7609	Intermediate Similarity	NPC137710
0.7606	Intermediate Similarity	NPC74612
0.76	Intermediate Similarity	NPC90296
0.7597	Intermediate Similarity	NPC471174
0.7597	Intermediate Similarity	NPC216755
0.7597	Intermediate Similarity	NPC302987
0.7595	Intermediate Similarity	NPC88958
0.7595	Intermediate Similarity	NPC75310
0.7593	Intermediate Similarity	NPC261184
0.7586	Intermediate Similarity	NPC183348
0.7586	Intermediate Similarity	NPC282230
0.7582	Intermediate Similarity	NPC5676
0.7578	Intermediate Similarity	NPC79571
0.7574	Intermediate Similarity	NPC28054
0.7569	Intermediate Similarity	NPC50583
0.7566	Intermediate Similarity	NPC64568
0.7562	Intermediate Similarity	NPC84349
0.7551	Intermediate Similarity	NPC470871
0.7548	Intermediate Similarity	NPC61284
0.7548	Intermediate Similarity	NPC113428
0.7547	Intermediate Similarity	NPC104736
0.7546	Intermediate Similarity	NPC475779
0.7536	Intermediate Similarity	NPC291619
0.7536	Intermediate Similarity	NPC254958
0.7535	Intermediate Similarity	NPC71274
0.7535	Intermediate Similarity	NPC75557
0.7532	Intermediate Similarity	NPC478166
0.7519	Intermediate Similarity	NPC177331
0.7518	Intermediate Similarity	NPC475818
0.7517	Intermediate Similarity	NPC66246
0.7517	Intermediate Similarity	NPC170546
0.7516	Intermediate Similarity	NPC272590
0.7516	Intermediate Similarity	NPC8389
0.7516	Intermediate Similarity	NPC472787
0.75	Intermediate Similarity	NPC319422
0.75	Intermediate Similarity	NPC477214
0.75	Intermediate Similarity	NPC234494
0.75	Intermediate Similarity	NPC211625
0.75	Intermediate Similarity	NPC159786
0.75	Intermediate Similarity	NPC477212
0.75	Intermediate Similarity	NPC470998
0.75	Intermediate Similarity	NPC477211
0.7484	Intermediate Similarity	NPC308799
0.7484	Intermediate Similarity	NPC286038
0.7484	Intermediate Similarity	NPC179170
0.7483	Intermediate Similarity	NPC474407
0.7483	Intermediate Similarity	NPC474425
0.7483	Intermediate Similarity	NPC470740
0.7483	Intermediate Similarity	NPC56197
0.7483	Intermediate Similarity	NPC471006
0.7483	Intermediate Similarity	NPC474426
0.7483	Intermediate Similarity	NPC18904
0.7481	Intermediate Similarity	NPC22678
0.7469	Intermediate Similarity	NPC68848
0.7469	Intermediate Similarity	NPC18986
0.7468	Intermediate Similarity	NPC469642
0.7468	Intermediate Similarity	NPC245522
0.7468	Intermediate Similarity	NPC114513
0.7468	Intermediate Similarity	NPC290038
0.7468	Intermediate Similarity	NPC145830
0.7468	Intermediate Similarity	NPC475777
0.7468	Intermediate Similarity	NPC247221
0.7467	Intermediate Similarity	NPC471996
0.7466	Intermediate Similarity	NPC298190
0.7465	Intermediate Similarity	NPC130275

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 NPC201370 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	1018
0.2-0.3	1546
0.3-0.4	2710
0.4-0.5	2221
0.5-0.6	1118
0.6-0.7	278
0.7-0.8	13
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
0.7784	Intermediate Similarity	NPD6784	Approved
0.7784	Intermediate Similarity	NPD6785	Approved
0.777	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6273	Approved
0.7255	Intermediate Similarity	NPD4534	Discontinued
0.7226	Intermediate Similarity	NPD3887	Approved
0.7203	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6355	Discontinued
0.719	Intermediate Similarity	NPD2344	Approved
0.7174	Intermediate Similarity	NPD1241	Discontinued
0.7171	Intermediate Similarity	NPD2799	Discontinued
0.7161	Intermediate Similarity	NPD4628	Phase 3
0.716	Intermediate Similarity	NPD5761	Phase 2
0.716	Intermediate Similarity	NPD5760	Phase 2
0.7143	Intermediate Similarity	NPD5958	Discontinued
0.7135	Intermediate Similarity	NPD6764	Approved
0.7135	Intermediate Similarity	NPD6765	Approved
0.7126	Intermediate Similarity	NPD8434	Phase 2
0.7115	Intermediate Similarity	NPD2354	Approved
0.7078	Intermediate Similarity	NPD1471	Phase 3
0.7075	Intermediate Similarity	NPD2798	Approved
0.7034	Intermediate Similarity	NPD3972	Approved
0.7006	Intermediate Similarity	NPD2309	Approved
0.7	Intermediate Similarity	NPD2313	Discontinued
0.6987	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6832	Phase 2
0.6968	Remote Similarity	NPD2353	Approved
0.6968	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD1876	Approved
0.6918	Remote Similarity	NPD9717	Approved
0.6913	Remote Similarity	NPD454	Approved
0.6909	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2796	Approved
0.6892	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2797	Approved
0.6887	Remote Similarity	NPD6798	Discontinued
0.6882	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6005	Phase 3
0.6859	Remote Similarity	NPD6004	Phase 3
0.6859	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6002	Phase 3
0.6855	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD9092	Discovery
0.6835	Remote Similarity	NPD7003	Approved
0.6831	Remote Similarity	NPD7157	Approved
0.6828	Remote Similarity	NPD5846	Approved
0.6828	Remote Similarity	NPD6516	Phase 2
0.6828	Remote Similarity	NPD1778	Approved
0.6826	Remote Similarity	NPD7075	Discontinued
0.681	Remote Similarity	NPD7458	Discontinued
0.681	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.679	Remote Similarity	NPD920	Approved
0.6779	Remote Similarity	NPD987	Approved
0.6776	Remote Similarity	NPD3268	Approved
0.677	Remote Similarity	NPD4661	Approved
0.677	Remote Similarity	NPD4662	Approved
0.677	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6599	Discontinued
0.6757	Remote Similarity	NPD4359	Approved
0.6752	Remote Similarity	NPD2346	Discontinued
0.6743	Remote Similarity	NPD6559	Discontinued
0.6733	Remote Similarity	NPD5647	Approved
0.6732	Remote Similarity	NPD8032	Phase 2
0.6731	Remote Similarity	NPD4308	Phase 3
0.673	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD958	Approved
0.6714	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD1549	Phase 2
0.6709	Remote Similarity	NPD2424	Discontinued
0.6708	Remote Similarity	NPD6799	Approved
0.6707	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD2684	Approved
0.6689	Remote Similarity	NPD1608	Approved
0.6689	Remote Similarity	NPD9494	Approved
0.6688	Remote Similarity	NPD3140	Approved
0.6688	Remote Similarity	NPD3142	Approved
0.6688	Remote Similarity	NPD4140	Approved
0.6688	Remote Similarity	NPD1551	Phase 2
0.6688	Remote Similarity	NPD2935	Discontinued
0.6687	Remote Similarity	NPD6844	Discontinued
0.6687	Remote Similarity	NPD5403	Approved
0.6687	Remote Similarity	NPD6801	Discontinued
0.6686	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD919	Approved
0.6667	Remote Similarity	NPD6362	Approved
0.6667	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD3496	Discontinued
0.6667	Remote Similarity	NPD1203	Approved
0.6667	Remote Similarity	NPD1243	Approved
0.6667	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7819	Suspended
0.6646	Remote Similarity	NPD7236	Approved
0.6646	Remote Similarity	NPD957	Approved
0.6646	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5763	Approved
0.6646	Remote Similarity	NPD5762	Approved
0.6646	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD5585	Approved
0.6643	Remote Similarity	NPD2629	Approved
0.6642	Remote Similarity	NPD1237	Approved
0.6626	Remote Similarity	NPD5049	Phase 3
0.6625	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD4110	Phase 3
0.6623	Remote Similarity	NPD4062	Phase 3
0.6623	Remote Similarity	NPD1019	Discontinued
0.6623	Remote Similarity	NPD6233	Phase 2
0.662	Remote Similarity	NPD7843	Approved
0.6619	Remote Similarity	NPD290	Approved
0.6609	Remote Similarity	NPD2163	Approved
0.6608	Remote Similarity	NPD8127	Discontinued
0.6608	Remote Similarity	NPD1247	Approved
0.6606	Remote Similarity	NPD2649	Approved
0.6606	Remote Similarity	NPD2651	Approved
0.6603	Remote Similarity	NPD6653	Approved
0.6601	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD7095	Approved
0.6587	Remote Similarity	NPD6279	Approved
0.6587	Remote Similarity	NPD6280	Approved
0.6585	Remote Similarity	NPD3869	Phase 3
0.6585	Remote Similarity	NPD3873	Phase 3
0.6582	Remote Similarity	NPD6099	Approved
0.6582	Remote Similarity	NPD4476	Approved
0.6582	Remote Similarity	NPD4477	Approved
0.6582	Remote Similarity	NPD6100	Approved
0.6581	Remote Similarity	NPD1240	Approved
0.6581	Remote Similarity	NPD4307	Phase 2
0.6575	Remote Similarity	NPD1894	Discontinued
0.6575	Remote Similarity	NPD9545	Approved
0.6566	Remote Similarity	NPD4380	Phase 2
0.6564	Remote Similarity	NPD1578	Phase 2
0.6562	Remote Similarity	NPD2800	Approved
0.6558	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD411	Approved
0.6556	Remote Similarity	NPD3267	Approved
0.6556	Remote Similarity	NPD3266	Approved
0.6552	Remote Similarity	NPD9493	Approved
0.6548	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD3134	Approved
0.6545	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5735	Approved
0.6538	Remote Similarity	NPD447	Suspended
0.6538	Remote Similarity	NPD1184	Approved
0.6533	Remote Similarity	NPD5327	Phase 3
0.6531	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD7411	Suspended
0.6522	Remote Similarity	NPD3750	Approved
0.6522	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD1510	Phase 2
0.6519	Remote Similarity	NPD5588	Approved
0.6519	Remote Similarity	NPD7033	Discontinued
0.6509	Remote Similarity	NPD2296	Approved
0.6509	Remote Similarity	NPD5402	Approved
0.6497	Remote Similarity	NPD1607	Approved
0.6494	Remote Similarity	NPD2403	Approved
0.6494	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.649	Remote Similarity	NPD1283	Approved
0.6488	Remote Similarity	NPD7577	Discontinued
0.6486	Remote Similarity	NPD17	Approved
0.6483	Remote Similarity	NPD6671	Approved
0.6477	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4060	Phase 1
0.6471	Remote Similarity	NPD7768	Phase 2
0.6463	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD4536	Approved
0.6456	Remote Similarity	NPD7097	Phase 1
0.6456	Remote Similarity	NPD4538	Approved
0.6456	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD5494	Approved
0.6452	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7239	Suspended
0.6442	Remote Similarity	NPD7440	Discontinued
0.6433	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3274	Phase 2
0.6429	Remote Similarity	NPD6677	Suspended
0.642	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD1651	Approved
0.6419	Remote Similarity	NPD5691	Approved
0.6415	Remote Similarity	NPD3748	Approved
0.6414	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5451	Approved
0.6407	Remote Similarity	NPD3226	Approved
0.6407	Remote Similarity	NPD3769	Discontinued
0.6405	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6166	Phase 2
0.64	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD2897	Discontinued
0.6392	Remote Similarity	NPD6353	Approved
0.6392	Remote Similarity	NPD6651	Approved
0.6391	Remote Similarity	NPD1934	Approved
0.6382	Remote Similarity	NPD6696	Suspended
0.6382	Remote Similarity	NPD8651	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