NPASS Compound

Structure

NPC474592 OpenBabel07101718282D 22 23 0 0 1 0 0 0 0 0999 V2000 -6.1409 1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9088 3.7216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4088 2.8555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3452 -0.2027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7790 0.6982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2748 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2748 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9088 0.2575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9088 0.2575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9088 1.9895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4088 2.8555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4088 1.1235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4088 1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9088 1.9895 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7818 1.6235 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.7818 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4088 1.1235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6828 2.0574 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 7 2 0 0 0 0 2 14 2 0 0 0 0 3 14 1 0 0 0 0 4 19 1 0 0 0 0 5 19 1 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 8 16 2 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 13 22 1 0 0 0 0 14 17 1 0 0 0 0 15 16 1 1 0 0 0 17 20 1 1 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 20 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	347.034
LogP:	4.586
LogD:	3.964
LogS:	-4.197
# Rotatable Bonds:	3
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.769
Synthetic Accessibility Score:	4.763
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.628
MDCK Permeability:	1.5716050256742164e-05
Pgp-inhibitor:	0.945
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.918
30% Bioavailability (F30%):	0.11

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.274
Plasma Protein Binding (PPB):	87.96119689941406%
Volume Distribution (VD):	1.927
Pgp-substrate:	9.222158432006836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.137
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.765
CYP2C9-inhibitor:	0.088
CYP2C9-substrate:	0.278
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.817
CYP3A4-inhibitor:	0.615
CYP3A4-substrate:	0.297

ADMET: Excretion

Clearance (CL):	4.156
Half-life (T1/2):	0.151

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.081
Drug-inuced Liver Injury (DILI):	0.075
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.15
Carcinogencity:	0.874
Eye Corrosion:	0.251
Eye Irritation:	0.702
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: NPC474592

Natural Product ID:	NPC474592
*Common Name:**	14,18-Epoxyloba-8,10,13(15)-Trien-17-Ol
IUPAC Name:	3-[(1S,3R,4R)-4-ethenyl-4-methyl-3-prop-1-en-2-ylcyclohexyl]-7,7-dimethyl-5,6-dihydro-2H-oxepin-6-ol
Synonyms:
Standard InCHIKey:	PUTSVFNWEZYJDF-BWBHZNDTSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-7-20(6)11-10-15(12-17(20)14(2)3)16-8-9-18(21)19(4,5)22-13-16/h7-8,15,17-18,21H,1-2,9-13H2,3-6H3/t15-,17+,18?,20-/m0/s1
SMILES:	CC(=C)C1CC(CCC1(C)C=C)C2=CCC(C(OC2)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476289
PubChem CID:	21604165
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002872] Elemane sesquiterpenoids

*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
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22209732]
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	Eukaryota	n.a.	Mindoro, Philippines	n.a.	PMID[9548875]
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	17.0	mm	PMID[503825]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	14.0	mm	PMID[503825]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	10.0	mm	PMID[503825]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	5.0	mm	PMID[503825]

☑ 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 NPC474592 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	182
0.1-0.2	1364
0.2-0.3	4897
0.3-0.4	14246
0.4-0.5	10363
0.5-0.6	8004
0.6-0.7	3248
0.7-0.8	380
0.8-0.85	9
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9342	High Similarity	NPC233295
0.8875	High Similarity	NPC49208
0.8875	High Similarity	NPC23748
0.8519	High Similarity	NPC471408
0.8272	Intermediate Similarity	NPC233332
0.825	Intermediate Similarity	NPC83351
0.825	Intermediate Similarity	NPC167891
0.8243	Intermediate Similarity	NPC250977
0.8235	Intermediate Similarity	NPC476948
0.8095	Intermediate Similarity	NPC83702
0.8072	Intermediate Similarity	NPC155521
0.8068	Intermediate Similarity	NPC471453
0.8052	Intermediate Similarity	NPC34834
0.8046	Intermediate Similarity	NPC97103
0.8046	Intermediate Similarity	NPC115607
0.8046	Intermediate Similarity	NPC20946
0.8025	Intermediate Similarity	NPC137587
0.8	Intermediate Similarity	NPC274448
0.8	Intermediate Similarity	NPC157257
0.8	Intermediate Similarity	NPC8774
0.8	Intermediate Similarity	NPC471795
0.8	Intermediate Similarity	NPC265588
0.7975	Intermediate Similarity	NPC104644
0.7975	Intermediate Similarity	NPC471525
0.7952	Intermediate Similarity	NPC474752
0.7952	Intermediate Similarity	NPC82986
0.7952	Intermediate Similarity	NPC474683
0.7952	Intermediate Similarity	NPC474759
0.7952	Intermediate Similarity	NPC474731
0.7952	Intermediate Similarity	NPC7505
0.7927	Intermediate Similarity	NPC242767
0.7912	Intermediate Similarity	NPC227583
0.7912	Intermediate Similarity	NPC12103
0.7912	Intermediate Similarity	NPC98457
0.7907	Intermediate Similarity	NPC255143
0.7907	Intermediate Similarity	NPC281316
0.7901	Intermediate Similarity	NPC91594
0.7895	Intermediate Similarity	NPC114651
0.7889	Intermediate Similarity	NPC127718
0.7889	Intermediate Similarity	NPC65402
0.7882	Intermediate Similarity	NPC46320
0.7882	Intermediate Similarity	NPC470077
0.7875	Intermediate Similarity	NPC12696
0.7865	Intermediate Similarity	NPC303697
0.7848	Intermediate Similarity	NPC471799
0.7826	Intermediate Similarity	NPC474977
0.7826	Intermediate Similarity	NPC26307
0.7816	Intermediate Similarity	NPC245004
0.7816	Intermediate Similarity	NPC131329
0.7816	Intermediate Similarity	NPC149224
0.7805	Intermediate Similarity	NPC477089
0.7792	Intermediate Similarity	NPC272961
0.7792	Intermediate Similarity	NPC208999
0.7791	Intermediate Similarity	NPC477578
0.7791	Intermediate Similarity	NPC35933
0.7791	Intermediate Similarity	NPC290731
0.7778	Intermediate Similarity	NPC91654
0.7778	Intermediate Similarity	NPC256720
0.7778	Intermediate Similarity	NPC307776
0.7778	Intermediate Similarity	NPC474792
0.7778	Intermediate Similarity	NPC236228
0.7778	Intermediate Similarity	NPC67398
0.7765	Intermediate Similarity	NPC474634
0.7765	Intermediate Similarity	NPC470558
0.7763	Intermediate Similarity	NPC267027
0.775	Intermediate Similarity	NPC471797
0.775	Intermediate Similarity	NPC201048
0.775	Intermediate Similarity	NPC476366
0.7738	Intermediate Similarity	NPC47761
0.7738	Intermediate Similarity	NPC264245
0.7722	Intermediate Similarity	NPC471271
0.7722	Intermediate Similarity	NPC477792
0.7722	Intermediate Similarity	NPC471268
0.7722	Intermediate Similarity	NPC167706
0.7722	Intermediate Similarity	NPC242001
0.7717	Intermediate Similarity	NPC288970
0.7711	Intermediate Similarity	NPC476701
0.7711	Intermediate Similarity	NPC328714
0.7701	Intermediate Similarity	NPC476217
0.7692	Intermediate Similarity	NPC473893
0.7692	Intermediate Similarity	NPC471560
0.7683	Intermediate Similarity	NPC40049
0.7683	Intermediate Similarity	NPC470711
0.7683	Intermediate Similarity	NPC470758
0.7674	Intermediate Similarity	NPC15534
0.7662	Intermediate Similarity	NPC68703
0.7662	Intermediate Similarity	NPC69649
0.7654	Intermediate Similarity	NPC32832
0.7654	Intermediate Similarity	NPC477923
0.7654	Intermediate Similarity	NPC66566
0.7647	Intermediate Similarity	NPC49964
0.7647	Intermediate Similarity	NPC470049
0.7647	Intermediate Similarity	NPC304285
0.764	Intermediate Similarity	NPC309310
0.764	Intermediate Similarity	NPC82876
0.764	Intermediate Similarity	NPC49783
0.764	Intermediate Similarity	NPC246028
0.7625	Intermediate Similarity	NPC130665
0.7619	Intermediate Similarity	NPC241290
0.7619	Intermediate Similarity	NPC164840
0.7619	Intermediate Similarity	NPC234193
0.7619	Intermediate Similarity	NPC209944
0.7614	Intermediate Similarity	NPC471796
0.7614	Intermediate Similarity	NPC189777
0.7595	Intermediate Similarity	NPC189745
0.7595	Intermediate Similarity	NPC145498
0.759	Intermediate Similarity	NPC476314
0.7586	Intermediate Similarity	NPC266511
0.7582	Intermediate Similarity	NPC53555
0.7564	Intermediate Similarity	NPC471238
0.7564	Intermediate Similarity	NPC476945
0.7561	Intermediate Similarity	NPC470749
0.7561	Intermediate Similarity	NPC477925
0.7561	Intermediate Similarity	NPC274079
0.7561	Intermediate Similarity	NPC315261
0.7558	Intermediate Similarity	NPC475789
0.7558	Intermediate Similarity	NPC317458
0.7556	Intermediate Similarity	NPC295668
0.7532	Intermediate Similarity	NPC279434
0.7532	Intermediate Similarity	NPC202017
0.7532	Intermediate Similarity	NPC476406
0.7531	Intermediate Similarity	NPC477138
0.7531	Intermediate Similarity	NPC243342
0.7531	Intermediate Similarity	NPC306727
0.7529	Intermediate Similarity	NPC70927
0.7529	Intermediate Similarity	NPC25554
0.7529	Intermediate Similarity	NPC476646
0.7528	Intermediate Similarity	NPC471952
0.75	Intermediate Similarity	NPC225415
0.75	Intermediate Similarity	NPC471272
0.75	Intermediate Similarity	NPC476367
0.75	Intermediate Similarity	NPC28862
0.75	Intermediate Similarity	NPC109546
0.75	Intermediate Similarity	NPC143182
0.75	Intermediate Similarity	NPC290367
0.75	Intermediate Similarity	NPC242992
0.75	Intermediate Similarity	NPC81306
0.75	Intermediate Similarity	NPC469491
0.75	Intermediate Similarity	NPC47982
0.75	Intermediate Similarity	NPC17550
0.75	Intermediate Similarity	NPC125399
0.75	Intermediate Similarity	NPC84694
0.75	Intermediate Similarity	NPC100906
0.75	Intermediate Similarity	NPC72755
0.7474	Intermediate Similarity	NPC473510
0.7474	Intermediate Similarity	NPC38855
0.7473	Intermediate Similarity	NPC475972
0.7473	Intermediate Similarity	NPC302584
0.7471	Intermediate Similarity	NPC205845
0.7471	Intermediate Similarity	NPC474047
0.7471	Intermediate Similarity	NPC185568
0.7471	Intermediate Similarity	NPC238485
0.747	Intermediate Similarity	NPC155986
0.747	Intermediate Similarity	NPC470751
0.747	Intermediate Similarity	NPC130136
0.747	Intermediate Similarity	NPC471798
0.747	Intermediate Similarity	NPC283619
0.747	Intermediate Similarity	NPC477426
0.747	Intermediate Similarity	NPC198968
0.747	Intermediate Similarity	NPC474826
0.747	Intermediate Similarity	NPC169994
0.747	Intermediate Similarity	NPC318495
0.747	Intermediate Similarity	NPC477427
0.747	Intermediate Similarity	NPC477924
0.747	Intermediate Similarity	NPC470750
0.747	Intermediate Similarity	NPC477425
0.7468	Intermediate Similarity	NPC474248
0.7468	Intermediate Similarity	NPC472947
0.7468	Intermediate Similarity	NPC9942
0.7447	Intermediate Similarity	NPC239547
0.7447	Intermediate Similarity	NPC96597
0.7447	Intermediate Similarity	NPC155319
0.7447	Intermediate Similarity	NPC125551
0.7447	Intermediate Similarity	NPC309503
0.7447	Intermediate Similarity	NPC210337
0.7447	Intermediate Similarity	NPC261807
0.7447	Intermediate Similarity	NPC91197
0.7442	Intermediate Similarity	NPC50964
0.7442	Intermediate Similarity	NPC259858
0.7442	Intermediate Similarity	NPC218616
0.7442	Intermediate Similarity	NPC296701
0.7442	Intermediate Similarity	NPC87489
0.7439	Intermediate Similarity	NPC291503
0.7436	Intermediate Similarity	NPC474477
0.7436	Intermediate Similarity	NPC197805
0.7423	Intermediate Similarity	NPC194323
0.7416	Intermediate Similarity	NPC166857
0.7416	Intermediate Similarity	NPC233744
0.7412	Intermediate Similarity	NPC287749
0.7412	Intermediate Similarity	NPC13554
0.7412	Intermediate Similarity	NPC96362
0.7407	Intermediate Similarity	NPC220939
0.7407	Intermediate Similarity	NPC474140
0.7407	Intermediate Similarity	NPC329763
0.7407	Intermediate Similarity	NPC265485
0.7407	Intermediate Similarity	NPC182717
0.7407	Intermediate Similarity	NPC68443
0.7396	Intermediate Similarity	NPC473174
0.7391	Intermediate Similarity	NPC119379
0.7386	Intermediate Similarity	NPC119001

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 NPC474592 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1695
0.2-0.3	3912
0.3-0.4	2251
0.4-0.5	758
0.5-0.6	290
0.6-0.7	73
0.7-0.8	3
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
0.7561	Intermediate Similarity	NPD6933	Approved
0.7416	Intermediate Similarity	NPD7524	Approved
0.7317	Intermediate Similarity	NPD6924	Approved
0.7317	Intermediate Similarity	NPD6926	Approved
0.7229	Intermediate Similarity	NPD6942	Approved
0.7229	Intermediate Similarity	NPD7339	Approved
0.7229	Intermediate Similarity	NPD8264	Approved
0.7176	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6695	Phase 3
0.7143	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7645	Phase 2
0.7079	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7332	Phase 2
0.7011	Intermediate Similarity	NPD7525	Registered
0.7011	Intermediate Similarity	NPD6930	Phase 2
0.7011	Intermediate Similarity	NPD6931	Approved
0.7011	Intermediate Similarity	NPD7514	Phase 3
0.701	Intermediate Similarity	NPD4225	Approved
0.6951	Remote Similarity	NPD7143	Approved
0.6951	Remote Similarity	NPD7144	Approved
0.6905	Remote Similarity	NPD4784	Approved
0.6905	Remote Similarity	NPD4785	Approved
0.6897	Remote Similarity	NPD6929	Approved
0.6869	Remote Similarity	NPD5344	Discontinued
0.6867	Remote Similarity	NPD7152	Approved
0.6867	Remote Similarity	NPD7151	Approved
0.6867	Remote Similarity	NPD7150	Approved
0.686	Remote Similarity	NPD6932	Approved
0.6848	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7750	Discontinued
0.6829	Remote Similarity	NPD6922	Approved
0.6829	Remote Similarity	NPD6923	Approved
0.6818	Remote Similarity	NPD7509	Discontinued
0.6795	Remote Similarity	NPD368	Approved
0.6782	Remote Similarity	NPD7145	Approved
0.6742	Remote Similarity	NPD6902	Approved
0.6703	Remote Similarity	NPD4786	Approved
0.6702	Remote Similarity	NPD6051	Approved
0.67	Remote Similarity	NPD4159	Approved
0.6667	Remote Similarity	NPD5776	Phase 2
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD4243	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD6925	Approved
0.6632	Remote Similarity	NPD7838	Discovery
0.663	Remote Similarity	NPD6893	Approved
0.6606	Remote Similarity	NPD7115	Discovery
0.66	Remote Similarity	NPD7640	Approved
0.66	Remote Similarity	NPD7639	Approved
0.6562	Remote Similarity	NPD7087	Discontinued
0.6556	Remote Similarity	NPD6898	Phase 1
0.6517	Remote Similarity	NPD6683	Phase 2
0.6476	Remote Similarity	NPD6686	Approved
0.6465	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD46	Approved
0.6458	Remote Similarity	NPD6698	Approved
0.6447	Remote Similarity	NPD342	Phase 1
0.6444	Remote Similarity	NPD4748	Discontinued
0.6442	Remote Similarity	NPD6640	Phase 3
0.6436	Remote Similarity	NPD6648	Approved
0.6395	Remote Similarity	NPD4732	Discontinued
0.6392	Remote Similarity	NPD7637	Suspended
0.6344	Remote Similarity	NPD3133	Approved
0.6344	Remote Similarity	NPD3665	Phase 1
0.6344	Remote Similarity	NPD3666	Approved
0.6344	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4195	Approved
0.6327	Remote Similarity	NPD6399	Phase 3
0.6304	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7328	Approved
0.625	Remote Similarity	NPD4190	Phase 3
0.625	Remote Similarity	NPD7327	Approved
0.625	Remote Similarity	NPD8039	Approved
0.625	Remote Similarity	NPD5275	Approved
0.6228	Remote Similarity	NPD7503	Approved
0.6228	Remote Similarity	NPD8033	Approved
0.6224	Remote Similarity	NPD6079	Approved
0.6224	Remote Similarity	NPD6411	Approved
0.622	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4623	Approved
0.6211	Remote Similarity	NPD3618	Phase 1
0.6211	Remote Similarity	NPD4519	Discontinued
0.6204	Remote Similarity	NPD6371	Approved
0.6195	Remote Similarity	NPD7516	Approved
0.6186	Remote Similarity	NPD5328	Approved
0.6176	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5779	Approved
0.6162	Remote Similarity	NPD5778	Approved
0.6154	Remote Similarity	NPD4219	Approved
0.6145	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.614	Remote Similarity	NPD8294	Approved
0.614	Remote Similarity	NPD8377	Approved
0.6122	Remote Similarity	NPD5785	Approved
0.6111	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD1694	Approved
0.6105	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7748	Approved
0.6087	Remote Similarity	NPD8379	Approved
0.6087	Remote Similarity	NPD8335	Approved
0.6087	Remote Similarity	NPD8378	Approved
0.6087	Remote Similarity	NPD4820	Approved
0.6087	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4822	Approved
0.6087	Remote Similarity	NPD4821	Approved
0.6087	Remote Similarity	NPD8380	Approved
0.6087	Remote Similarity	NPD8296	Approved
0.6087	Remote Similarity	NPD4819	Approved
0.6078	Remote Similarity	NPD6084	Phase 2
0.6078	Remote Similarity	NPD6083	Phase 2
0.6075	Remote Similarity	NPD6412	Phase 2
0.6064	Remote Similarity	NPD5362	Discontinued
0.6064	Remote Similarity	NPD7154	Phase 3
0.6061	Remote Similarity	NPD7983	Approved
0.6061	Remote Similarity	NPD7515	Phase 2
0.6049	Remote Similarity	NPD1145	Discontinued
0.6044	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD7334	Approved
0.6042	Remote Similarity	NPD6409	Approved
0.6042	Remote Similarity	NPD5330	Approved
0.6042	Remote Similarity	NPD7146	Approved
0.6042	Remote Similarity	NPD6684	Approved
0.6042	Remote Similarity	NPD7521	Approved
0.6042	Remote Similarity	NPD5279	Phase 3
0.604	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.602	Remote Similarity	NPD6101	Approved
0.602	Remote Similarity	NPD4753	Phase 2
0.602	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4202	Approved
0.6	Remote Similarity	NPD3668	Phase 3
0.6	Remote Similarity	NPD7632	Discontinued
0.596	Remote Similarity	NPD3168	Discontinued
0.596	Remote Similarity	NPD7136	Phase 2
0.5957	Remote Similarity	NPD4221	Approved
0.5957	Remote Similarity	NPD4223	Phase 3
0.5946	Remote Similarity	NPD6053	Discontinued
0.5946	Remote Similarity	NPD8297	Approved
0.5938	Remote Similarity	NPD1696	Phase 3
0.5938	Remote Similarity	NPD5329	Approved
0.5926	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD7902	Approved
0.5918	Remote Similarity	NPD6903	Approved
0.5918	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD4695	Discontinued
0.5895	Remote Similarity	NPD5331	Approved
0.5895	Remote Similarity	NPD4788	Approved
0.5895	Remote Similarity	NPD5332	Approved
0.5882	Remote Similarity	NPD4629	Approved
0.5882	Remote Similarity	NPD7507	Approved
0.5882	Remote Similarity	NPD5210	Approved
0.5882	Remote Similarity	NPD5695	Phase 3
0.5876	Remote Similarity	NPD5690	Phase 2
0.5872	Remote Similarity	NPD6899	Approved
0.5872	Remote Similarity	NPD6881	Approved
0.587	Remote Similarity	NPD4271	Approved
0.587	Remote Similarity	NPD4268	Approved
0.5862	Remote Similarity	NPD7741	Discontinued
0.5862	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD4790	Discontinued
0.5851	Remote Similarity	NPD5369	Approved
0.5849	Remote Similarity	NPD5211	Phase 2
0.5833	Remote Similarity	NPD6675	Approved
0.5833	Remote Similarity	NPD6402	Approved
0.5833	Remote Similarity	NPD5739	Approved
0.5833	Remote Similarity	NPD4197	Approved
0.5833	Remote Similarity	NPD7128	Approved
0.5825	Remote Similarity	NPD5222	Approved
0.5825	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5221	Approved
0.581	Remote Similarity	NPD4696	Approved
0.581	Remote Similarity	NPD5286	Approved
0.581	Remote Similarity	NPD5285	Approved
0.5802	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4269	Approved
0.5789	Remote Similarity	NPD4270	Approved
0.5784	Remote Similarity	NPD5282	Discontinued
0.578	Remote Similarity	NPD5697	Approved
0.5773	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5173	Approved
0.5769	Remote Similarity	NPD4755	Approved
0.5766	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD7102	Approved
0.5766	Remote Similarity	NPD6883	Approved
0.5766	Remote Similarity	NPD7290	Approved
0.5758	Remote Similarity	NPD6672	Approved
0.5758	Remote Similarity	NPD5737	Approved
0.5755	Remote Similarity	NPD5223	Approved
0.5752	Remote Similarity	NPD4632	Approved
0.5752	Remote Similarity	NPD8133	Approved
0.5745	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5693	Phase 1
0.5741	Remote Similarity	NPD5141	Approved
0.5739	Remote Similarity	NPD4198	Discontinued
0.5738	Remote Similarity	NPD7319	Approved
0.5729	Remote Similarity	NPD6110	Phase 1
0.5727	Remote Similarity	NPD6011	Approved
0.5727	Remote Similarity	NPD7320	Approved
0.5714	Remote Similarity	NPD6869	Approved
0.5714	Remote Similarity	NPD6847	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