NPASS Compound

Structure

NPC473982 OpenBabel07101718332D 27 28 0 0 1 0 0 0 0 0999 V2000 1.3171 -7.9852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 2.3171 -1.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -7.1192 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 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8171 -7.1192 0.0000 C 0 0 3 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 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 3.3171 -7.9852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3171 -6.2532 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 5 1 0 0 0 0 2 18 1 0 0 0 0 5 21 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 7 14 2 0 0 0 0 8 12 1 0 0 0 0 8 15 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 18 2 0 0 0 0 12 20 1 0 0 0 0 13 16 2 0 0 0 0 13 20 1 0 0 0 0 14 24 1 0 0 0 0 15 24 1 0 0 0 0 16 27 1 0 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 19 3 1 1 0 0 0 20 23 2 0 0 0 0 21 22 1 0 0 0 0 21 25 1 0 0 0 0 22 26 2 0 0 0 0 23 24 1 0 0 0 0 23 27 1 0 0 0 0 24 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.27
Volume:	419.736
LogP:	4.965
LogD:	4.404
LogS:	-4.431
# Rotatable Bonds:	10
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.519
Synthetic Accessibility Score:	4.476
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.643
MDCK Permeability:	2.8122149160481058e-05
Pgp-inhibitor:	0.138
Pgp-substrate:	0.175
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.725
30% Bioavailability (F30%):	0.528

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.359
Plasma Protein Binding (PPB):	95.166748046875%
Volume Distribution (VD):	1.471
Pgp-substrate:	2.491095781326294%

ADMET: Metabolism

CYP1A2-inhibitor:	0.691
CYP1A2-substrate:	0.489
CYP2C19-inhibitor:	0.784
CYP2C19-substrate:	0.819
CYP2C9-inhibitor:	0.888
CYP2C9-substrate:	0.472
CYP2D6-inhibitor:	0.884
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.952
CYP3A4-substrate:	0.558

ADMET: Excretion

Clearance (CL):	11.964
Half-life (T1/2):	0.487

ADMET: Toxicity

hERG Blockers:	0.284
Human Hepatotoxicity (H-HT):	0.929
Drug-inuced Liver Injury (DILI):	0.265
AMES Toxicity:	0.167
Rat Oral Acute Toxicity:	0.934
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.265
Carcinogencity:	0.937
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC473982

Natural Product ID:	NPC473982
*Common Name:**	(6S,10Z,12E)-3-Hydroxy-6,10-Dimethyl-13-[(7S)-7-Methyl-5,6-Dihydro-4H-1-Benzofuran-7-Yl]Trideca-10,12-Dien-4-One
IUPAC Name:	(6S,10Z,12E)-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:	GHGXPVQCIKVWSW-QLQJQYTPSA-N
Standard InCHI:	InChI=1S/C24H36O3/c1-5-21(25)22(26)17-19(3)10-6-9-18(2)11-7-14-24(4)15-8-12-20-13-16-27-23(20)24/h7,11,13-14,16,19,21,25H,5-6,8-10,12,15,17H2,1-4H3/b14-7+,18-11-/t19-,21?,24+/m0/s1
SMILES:	CCC(C(=O)C[C@H](CCC/C(=CC=C[C@]1(C)CCCc2c1occ2)/C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457158
PubChem CID:	10474453
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[568879]

☑ 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 NPC473982 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	249
0.1-0.2	1319
0.2-0.3	3065
0.3-0.4	8013
0.4-0.5	11930
0.5-0.6	6447
0.6-0.7	9890
0.7-0.8	1648
0.8-0.85	105
0.85-0.9	27
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9394	High Similarity	NPC201370
0.9394	High Similarity	NPC473983
0.9062	High Similarity	NPC329707
0.8898	High Similarity	NPC118853
0.8881	High Similarity	NPC170604
0.8881	High Similarity	NPC215109
0.8837	High Similarity	NPC246392
0.8769	High Similarity	NPC26532
0.875	High Similarity	NPC202260
0.874	High Similarity	NPC477967
0.8712	High Similarity	NPC61788
0.8702	High Similarity	NPC59502
0.8692	High Similarity	NPC290955
0.8682	High Similarity	NPC473885
0.8682	High Similarity	NPC471074
0.8676	High Similarity	NPC472376
0.8661	High Similarity	NPC97566
0.8615	High Similarity	NPC23086
0.8593	High Similarity	NPC476947
0.8582	High Similarity	NPC218838
0.8571	High Similarity	NPC243704
0.8561	High Similarity	NPC263337
0.855	High Similarity	NPC474830
0.8538	High Similarity	NPC474829
0.8538	High Similarity	NPC290193
0.8492	Intermediate Similarity	NPC312525
0.8492	Intermediate Similarity	NPC217180
0.8485	Intermediate Similarity	NPC279877
0.848	Intermediate Similarity	NPC205523
0.8473	Intermediate Similarity	NPC138139
0.8473	Intermediate Similarity	NPC46536
0.8467	Intermediate Similarity	NPC307401
0.8467	Intermediate Similarity	NPC278832
0.8467	Intermediate Similarity	NPC473268
0.8467	Intermediate Similarity	NPC64157
0.8433	Intermediate Similarity	NPC89133
0.8417	Intermediate Similarity	NPC148374
0.8397	Intermediate Similarity	NPC300098
0.8382	Intermediate Similarity	NPC106247
0.837	Intermediate Similarity	NPC471817
0.8369	Intermediate Similarity	NPC243577
0.8358	Intermediate Similarity	NPC939
0.8356	Intermediate Similarity	NPC294511
0.8356	Intermediate Similarity	NPC121615
0.8346	Intermediate Similarity	NPC208906
0.8346	Intermediate Similarity	NPC112706
0.8346	Intermediate Similarity	NPC144745
0.8346	Intermediate Similarity	NPC207294
0.8345	Intermediate Similarity	NPC212257
0.8333	Intermediate Similarity	NPC150895
0.8333	Intermediate Similarity	NPC470858
0.8333	Intermediate Similarity	NPC93666
0.8321	Intermediate Similarity	NPC243269
0.8321	Intermediate Similarity	NPC265793
0.8321	Intermediate Similarity	NPC178382
0.8309	Intermediate Similarity	NPC293253
0.8296	Intermediate Similarity	NPC477645
0.8286	Intermediate Similarity	NPC67003
0.8284	Intermediate Similarity	NPC208389
0.8281	Intermediate Similarity	NPC21831
0.8281	Intermediate Similarity	NPC187547
0.8271	Intermediate Similarity	NPC83178
0.8268	Intermediate Similarity	NPC59035
0.8268	Intermediate Similarity	NPC79202
0.8268	Intermediate Similarity	NPC474987
0.8261	Intermediate Similarity	NPC46896
0.8261	Intermediate Similarity	NPC303217
0.8244	Intermediate Similarity	NPC16922
0.8231	Intermediate Similarity	NPC79557
0.8231	Intermediate Similarity	NPC246164
0.8209	Intermediate Similarity	NPC477123
0.8209	Intermediate Similarity	NPC477040
0.8209	Intermediate Similarity	NPC477966
0.82	Intermediate Similarity	NPC116639
0.8195	Intermediate Similarity	NPC474260
0.8195	Intermediate Similarity	NPC329922
0.8195	Intermediate Similarity	NPC329694
0.8195	Intermediate Similarity	NPC81912
0.8188	Intermediate Similarity	NPC158525
0.8182	Intermediate Similarity	NPC11799
0.8182	Intermediate Similarity	NPC65735
0.8182	Intermediate Similarity	NPC477965
0.8182	Intermediate Similarity	NPC188377
0.8182	Intermediate Similarity	NPC477038
0.8182	Intermediate Similarity	NPC141252
0.8169	Intermediate Similarity	NPC52412
0.8168	Intermediate Similarity	NPC263870
0.8168	Intermediate Similarity	NPC471549
0.8168	Intermediate Similarity	NPC473379
0.8168	Intermediate Similarity	NPC317217
0.8143	Intermediate Similarity	NPC177262
0.8143	Intermediate Similarity	NPC130976
0.814	Intermediate Similarity	NPC87466
0.814	Intermediate Similarity	NPC206007
0.8138	Intermediate Similarity	NPC71821
0.8134	Intermediate Similarity	NPC476016
0.8133	Intermediate Similarity	NPC194499
0.8125	Intermediate Similarity	NPC185456
0.8125	Intermediate Similarity	NPC56731
0.812	Intermediate Similarity	NPC179354
0.812	Intermediate Similarity	NPC303010
0.8112	Intermediate Similarity	NPC476946
0.8106	Intermediate Similarity	NPC272899
0.8102	Intermediate Similarity	NPC15083
0.8102	Intermediate Similarity	NPC470976
0.8102	Intermediate Similarity	NPC471995
0.8102	Intermediate Similarity	NPC196979
0.8102	Intermediate Similarity	NPC470977
0.8099	Intermediate Similarity	NPC205765
0.8099	Intermediate Similarity	NPC477537
0.8099	Intermediate Similarity	NPC477535
0.8095	Intermediate Similarity	NPC228842
0.8088	Intermediate Similarity	NPC476925
0.8085	Intermediate Similarity	NPC107571
0.8085	Intermediate Similarity	NPC90953
0.8079	Intermediate Similarity	NPC472823
0.8079	Intermediate Similarity	NPC474611
0.8077	Intermediate Similarity	NPC137710
0.8077	Intermediate Similarity	NPC473969
0.8074	Intermediate Similarity	NPC476917
0.8074	Intermediate Similarity	NPC474279
0.8074	Intermediate Similarity	NPC474438
0.8074	Intermediate Similarity	NPC477039
0.8074	Intermediate Similarity	NPC327527
0.8067	Intermediate Similarity	NPC41880
0.806	Intermediate Similarity	NPC74612
0.8058	Intermediate Similarity	NPC477210
0.8058	Intermediate Similarity	NPC209858
0.8056	Intermediate Similarity	NPC158871
0.8054	Intermediate Similarity	NPC44606
0.8047	Intermediate Similarity	NPC28054
0.8042	Intermediate Similarity	NPC121158
0.8029	Intermediate Similarity	NPC282230
0.8029	Intermediate Similarity	NPC183348
0.8028	Intermediate Similarity	NPC90296
0.8015	Intermediate Similarity	NPC50583
0.8014	Intermediate Similarity	NPC302987
0.8014	Intermediate Similarity	NPC216755
0.8014	Intermediate Similarity	NPC471174
0.8013	Intermediate Similarity	NPC195954
0.8013	Intermediate Similarity	NPC88007
0.8013	Intermediate Similarity	NPC7059
0.8013	Intermediate Similarity	NPC304692
0.8	Intermediate Similarity	NPC75310
0.8	Intermediate Similarity	NPC291619
0.8	Intermediate Similarity	NPC88958
0.8	Intermediate Similarity	NPC5676
0.8	Intermediate Similarity	NPC254958
0.8	Intermediate Similarity	NPC177331
0.7987	Intermediate Similarity	NPC261184
0.7986	Intermediate Similarity	NPC64568
0.7986	Intermediate Similarity	NPC470871
0.7985	Intermediate Similarity	NPC71274
0.7985	Intermediate Similarity	NPC75557
0.7974	Intermediate Similarity	NPC79571
0.797	Intermediate Similarity	NPC475818
0.7961	Intermediate Similarity	NPC84349
0.7959	Intermediate Similarity	NPC113428
0.7959	Intermediate Similarity	NPC61284
0.7956	Intermediate Similarity	NPC66246
0.7956	Intermediate Similarity	NPC170546
0.7953	Intermediate Similarity	NPC22678
0.7947	Intermediate Similarity	NPC104736
0.7945	Intermediate Similarity	NPC478166
0.7941	Intermediate Similarity	NPC319422
0.7941	Intermediate Similarity	NPC477211
0.7941	Intermediate Similarity	NPC477214
0.7941	Intermediate Similarity	NPC477212
0.7935	Intermediate Similarity	NPC475779
0.7929	Intermediate Similarity	NPC159786
0.7923	Intermediate Similarity	NPC131801
0.7923	Intermediate Similarity	NPC227660
0.7919	Intermediate Similarity	NPC472787
0.7919	Intermediate Similarity	NPC272590
0.7914	Intermediate Similarity	NPC470740
0.7914	Intermediate Similarity	NPC471006
0.7914	Intermediate Similarity	NPC474426
0.7914	Intermediate Similarity	NPC474425
0.7914	Intermediate Similarity	NPC474407
0.791	Intermediate Similarity	NPC130275
0.7908	Intermediate Similarity	NPC8389
0.7905	Intermediate Similarity	NPC470998
0.7905	Intermediate Similarity	NPC234494
0.7905	Intermediate Similarity	NPC211625
0.7903	Intermediate Similarity	NPC42471
0.7902	Intermediate Similarity	NPC18904
0.7902	Intermediate Similarity	NPC56197
0.7899	Intermediate Similarity	NPC298190
0.7891	Intermediate Similarity	NPC286038
0.7891	Intermediate Similarity	NPC308799
0.7887	Intermediate Similarity	NPC471996
0.7883	Intermediate Similarity	NPC223063
0.7883	Intermediate Similarity	NPC120836
0.7881	Intermediate Similarity	NPC179170
0.7877	Intermediate Similarity	NPC114513
0.7877	Intermediate Similarity	NPC469642
0.7877	Intermediate Similarity	NPC245522
0.7877	Intermediate Similarity	NPC247221
0.7877	Intermediate Similarity	NPC290038
0.7872	Intermediate Similarity	NPC146872

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 NPC473982 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	251
0.1-0.2	946
0.2-0.3	1515
0.3-0.4	2549
0.4-0.5	2194
0.5-0.6	1236
0.6-0.7	415
0.7-0.8	44
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
0.8214	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6273	Approved
0.763	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD1241	Discontinued
0.7606	Intermediate Similarity	NPD6355	Discontinued
0.7586	Intermediate Similarity	NPD2344	Approved
0.7569	Intermediate Similarity	NPD2799	Discontinued
0.7551	Intermediate Similarity	NPD4628	Phase 3
0.7532	Intermediate Similarity	NPD5760	Phase 2
0.7532	Intermediate Similarity	NPD5761	Phase 2
0.7485	Intermediate Similarity	NPD6765	Approved
0.7485	Intermediate Similarity	NPD6764	Approved
0.7482	Intermediate Similarity	NPD2798	Approved
0.747	Intermediate Similarity	NPD8434	Phase 2
0.7466	Intermediate Similarity	NPD1471	Phase 3
0.7445	Intermediate Similarity	NPD3972	Approved
0.7394	Intermediate Similarity	NPD2313	Discontinued
0.7383	Intermediate Similarity	NPD2309	Approved
0.7376	Intermediate Similarity	NPD6832	Phase 2
0.7365	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1876	Approved
0.7319	Intermediate Similarity	NPD9717	Approved
0.7308	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6785	Approved
0.7305	Intermediate Similarity	NPD6784	Approved
0.7286	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD2797	Approved
0.7279	Intermediate Similarity	NPD2796	Approved
0.7273	Intermediate Similarity	NPD6798	Discontinued
0.7261	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD9092	Discovery
0.7239	Intermediate Similarity	NPD7157	Approved
0.7237	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6005	Phase 3
0.723	Intermediate Similarity	NPD6004	Phase 3
0.723	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6002	Phase 3
0.7226	Intermediate Similarity	NPD1778	Approved
0.7222	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7003	Approved
0.717	Intermediate Similarity	NPD7075	Discontinued
0.7161	Intermediate Similarity	NPD7458	Discontinued
0.7161	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3268	Approved
0.7143	Intermediate Similarity	NPD920	Approved
0.7124	Intermediate Similarity	NPD4662	Approved
0.7124	Intermediate Similarity	NPD4661	Approved
0.7124	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6599	Discontinued
0.7114	Intermediate Similarity	NPD2346	Discontinued
0.7113	Intermediate Similarity	NPD5647	Approved
0.7103	Intermediate Similarity	NPD8032	Phase 2
0.7101	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2684	Approved
0.7095	Intermediate Similarity	NPD4308	Phase 3
0.7086	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1608	Approved
0.7067	Intermediate Similarity	NPD4534	Discontinued
0.7067	Intermediate Similarity	NPD2424	Discontinued
0.7067	Intermediate Similarity	NPD1549	Phase 2
0.7066	Intermediate Similarity	NPD6559	Discontinued
0.7063	Intermediate Similarity	NPD9494	Approved
0.7059	Intermediate Similarity	NPD6799	Approved
0.7055	Intermediate Similarity	NPD4140	Approved
0.7055	Intermediate Similarity	NPD3140	Approved
0.7055	Intermediate Similarity	NPD3142	Approved
0.7054	Intermediate Similarity	NPD1237	Approved
0.705	Intermediate Similarity	NPD3496	Discontinued
0.7047	Intermediate Similarity	NPD1551	Phase 2
0.7047	Intermediate Similarity	NPD2935	Discontinued
0.7044	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6362	Approved
0.7042	Intermediate Similarity	NPD1203	Approved
0.7039	Intermediate Similarity	NPD3887	Approved
0.7037	Intermediate Similarity	NPD2629	Approved
0.7032	Intermediate Similarity	NPD5403	Approved
0.7029	Intermediate Similarity	NPD5585	Approved
0.7025	Intermediate Similarity	NPD6844	Discontinued
0.7025	Intermediate Similarity	NPD6801	Discontinued
0.7023	Intermediate Similarity	NPD290	Approved
0.702	Intermediate Similarity	NPD1243	Approved
0.7019	Intermediate Similarity	NPD919	Approved
0.7019	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7843	Approved
0.7013	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5401	Approved
0.7	Intermediate Similarity	NPD3882	Suspended
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5763	Approved
0.7	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7236	Approved
0.6993	Remote Similarity	NPD1019	Discontinued
0.6986	Remote Similarity	NPD4062	Phase 3
0.6986	Remote Similarity	NPD6233	Phase 2
0.6981	Remote Similarity	NPD7819	Suspended
0.6974	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4110	Phase 3
0.6968	Remote Similarity	NPD5049	Phase 3
0.6966	Remote Similarity	NPD7095	Approved
0.6959	Remote Similarity	NPD6653	Approved
0.6957	Remote Similarity	NPD9545	Approved
0.6957	Remote Similarity	NPD1894	Discontinued
0.6954	Remote Similarity	NPD5958	Discontinued
0.6947	Remote Similarity	NPD3134	Approved
0.6943	Remote Similarity	NPD2651	Approved
0.6943	Remote Similarity	NPD2649	Approved
0.6939	Remote Similarity	NPD1240	Approved
0.6939	Remote Similarity	NPD4307	Phase 2
0.6934	Remote Similarity	NPD9493	Approved
0.6933	Remote Similarity	NPD6100	Approved
0.6933	Remote Similarity	NPD6099	Approved
0.6933	Remote Similarity	NPD1247	Approved
0.6933	Remote Similarity	NPD8127	Discontinued
0.6933	Remote Similarity	NPD4476	Approved
0.6933	Remote Similarity	NPD4477	Approved
0.6928	Remote Similarity	NPD2354	Approved
0.6928	Remote Similarity	NPD2163	Approved
0.6923	Remote Similarity	NPD3266	Approved
0.6923	Remote Similarity	NPD3267	Approved
0.6923	Remote Similarity	NPD3873	Phase 3
0.6923	Remote Similarity	NPD3869	Phase 3
0.6918	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD411	Approved
0.6918	Remote Similarity	NPD6280	Approved
0.6918	Remote Similarity	NPD6279	Approved
0.6908	Remote Similarity	NPD2800	Approved
0.6906	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5327	Phase 3
0.6899	Remote Similarity	NPD4380	Phase 2
0.6892	Remote Similarity	NPD447	Suspended
0.6892	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5735	Approved
0.6875	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1510	Phase 2
0.6867	Remote Similarity	NPD7033	Discontinued
0.6863	Remote Similarity	NPD3750	Approved
0.6863	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6671	Approved
0.6857	Remote Similarity	NPD17	Approved
0.6855	Remote Similarity	NPD7411	Suspended
0.6853	Remote Similarity	NPD1283	Approved
0.6849	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1607	Approved
0.6832	Remote Similarity	NPD5402	Approved
0.6832	Remote Similarity	NPD2296	Approved
0.6824	Remote Similarity	NPD4060	Phase 1
0.6813	Remote Similarity	NPD7577	Discontinued
0.6803	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7097	Phase 1
0.6795	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7768	Phase 2
0.6788	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1651	Approved
0.6786	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5691	Approved
0.6783	Remote Similarity	NPD4359	Approved
0.6776	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2353	Approved
0.6774	Remote Similarity	NPD7440	Discontinued
0.6772	Remote Similarity	NPD7239	Suspended
0.6768	Remote Similarity	NPD5494	Approved
0.6759	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD3748	Approved
0.675	Remote Similarity	NPD6677	Suspended
0.6748	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD4626	Approved
0.6736	Remote Similarity	NPD8651	Approved
0.6736	Remote Similarity	NPD6696	Suspended
0.6733	Remote Similarity	NPD6651	Approved
0.6733	Remote Similarity	NPD6353	Approved
0.6732	Remote Similarity	NPD2897	Discontinued
0.673	Remote Similarity	NPD3226	Approved
0.6726	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD1934	Approved
0.6707	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6166	Phase 2
0.6707	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.669	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3764	Approved
0.6687	Remote Similarity	NPD6808	Phase 2
0.6667	Remote Similarity	NPD4618	Approved
0.6667	Remote Similarity	NPD1933	Approved
0.6667	Remote Similarity	NPD2067	Discontinued
0.6667	Remote Similarity	NPD3685	Discontinued
0.6667	Remote Similarity	NPD4622	Approved
0.6667	Remote Similarity	NPD2614	Approved
0.6648	Remote Similarity	NPD3057	Approved
0.6647	Remote Similarity	NPD3926	Phase 2
0.6646	Remote Similarity	NPD3749	Approved
0.6645	Remote Similarity	NPD8166	Discontinued
0.6644	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3691	Phase 2
0.6644	Remote Similarity	NPD3690	Phase 2
0.6644	Remote Similarity	NPD6663	Approved
0.6644	Remote Similarity	NPD4870	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