NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	263.425
LogP:	4.293
LogD:	3.46
LogS:	-3.222
# Rotatable Bonds:	0
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.737
Synthetic Accessibility Score:	4.013
Fsp3:	0.733
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:	-4.864
MDCK Permeability:	2.5123421437456273e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.156
Plasma Protein Binding (PPB):	95.1111831665039%
Volume Distribution (VD):	1.992
Pgp-substrate:	6.829235076904297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.088
CYP1A2-substrate:	0.659
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.538
CYP2C9-inhibitor:	0.252
CYP2C9-substrate:	0.886
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.444
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.128

ADMET: Excretion

Clearance (CL):	14.073
Half-life (T1/2):	0.554

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.248
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.847
Maximum Recommended Daily Dose:	0.214
Skin Sensitization:	0.549
Carcinogencity:	0.856
Eye Corrosion:	0.013
Eye Irritation:	0.406
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC474062

Natural Product ID:	NPC474062
*Common Name:**	11-Epivaldiviolide
IUPAC Name:	(1S,5aS,9aS)-1-hydroxy-6,6,9a-trimethyl-4,5,5a,7,8,9-hexahydro-1H-benzo[e][2]benzofuran-3-one
Synonyms:	11-Epivaldiviolide
Standard InCHIKey:	XTQKCVAXPOCYKT-XEGUGMAKSA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-14(2)7-4-8-15(3)10(14)6-5-9-11(15)13(17)18-12(9)16/h10,13,17H,4-8H2,1-3H3/t10-,13-,15-/m0/s1
SMILES:	CC1(CCCC2(C1CCC3=C2C(OC3=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459608
PubChem CID:	10354740
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO8660	Dendrodoris carbunculosa	Species	Dendrodorididae	Eukaryota	n.a.	Amatsu-kominato, Boso Peninsula, central Japan (35 07N, 140 11E)	1999-NOV	PMID[11421732]
NPO8660	Dendrodoris carbunculosa	Species	Dendrodorididae	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
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	3.2	ug.mL-1	PMID[465078]
NPT168	Cell Line	P388	Mus musculus	IC50	=	2.5	ug.mL-1	PMID[465078]

☑ 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 NPC474062 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	183
0.1-0.2	1233
0.2-0.3	5378
0.3-0.4	13292
0.4-0.5	10619
0.5-0.6	7330
0.6-0.7	3952
0.7-0.8	642
0.8-0.85	50
0.85-0.9	10
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9195	High Similarity	NPC474554
0.9195	High Similarity	NPC474555
0.907	High Similarity	NPC477782
0.9036	High Similarity	NPC71626
0.8989	High Similarity	NPC240673
0.8989	High Similarity	NPC17578
0.8966	High Similarity	NPC477783
0.8953	High Similarity	NPC251528
0.8929	High Similarity	NPC473251
0.8929	High Similarity	NPC42586
0.8875	High Similarity	NPC316500
0.8864	High Similarity	NPC166346
0.8636	High Similarity	NPC232426
0.8636	High Similarity	NPC281942
0.8602	High Similarity	NPC471075
0.8571	High Similarity	NPC470801
0.8539	High Similarity	NPC141831
0.8539	High Similarity	NPC165904
0.8539	High Similarity	NPC179517
0.8523	High Similarity	NPC470734
0.8523	High Similarity	NPC5509
0.8506	High Similarity	NPC312561
0.8506	High Similarity	NPC475678
0.8495	Intermediate Similarity	NPC477720
0.8488	Intermediate Similarity	NPC86316
0.8488	Intermediate Similarity	NPC106416
0.8478	Intermediate Similarity	NPC475709
0.8452	Intermediate Similarity	NPC282293
0.8444	Intermediate Similarity	NPC115021
0.8333	Intermediate Similarity	NPC477122
0.8315	Intermediate Similarity	NPC174342
0.8315	Intermediate Similarity	NPC168131
0.8276	Intermediate Similarity	NPC65661
0.8242	Intermediate Similarity	NPC242069
0.8242	Intermediate Similarity	NPC472303
0.8211	Intermediate Similarity	NPC63249
0.8202	Intermediate Similarity	NPC472809
0.8202	Intermediate Similarity	NPC472810
0.8152	Intermediate Similarity	NPC298973
0.8152	Intermediate Similarity	NPC104925
0.8152	Intermediate Similarity	NPC475572
0.8132	Intermediate Similarity	NPC289479
0.8132	Intermediate Similarity	NPC65513
0.8132	Intermediate Similarity	NPC472814
0.8132	Intermediate Similarity	NPC177037
0.8125	Intermediate Similarity	NPC134077
0.8105	Intermediate Similarity	NPC472644
0.8105	Intermediate Similarity	NPC476767
0.8085	Intermediate Similarity	NPC208094
0.8081	Intermediate Similarity	NPC90946
0.8081	Intermediate Similarity	NPC300614
0.8081	Intermediate Similarity	NPC325054
0.8068	Intermediate Similarity	NPC474860
0.8068	Intermediate Similarity	NPC189311
0.8068	Intermediate Similarity	NPC471300
0.8046	Intermediate Similarity	NPC472440
0.8046	Intermediate Similarity	NPC22611
0.8043	Intermediate Similarity	NPC469939
0.8041	Intermediate Similarity	NPC471208
0.8022	Intermediate Similarity	NPC51486
0.8	Intermediate Similarity	NPC31522
0.7979	Intermediate Similarity	NPC154526
0.7979	Intermediate Similarity	NPC472363
0.7979	Intermediate Similarity	NPC472362
0.7978	Intermediate Similarity	NPC250981
0.7957	Intermediate Similarity	NPC469697
0.7957	Intermediate Similarity	NPC324078
0.7955	Intermediate Similarity	NPC470800
0.7935	Intermediate Similarity	NPC472811
0.7931	Intermediate Similarity	NPC200513
0.7907	Intermediate Similarity	NPC10636
0.7907	Intermediate Similarity	NPC195424
0.79	Intermediate Similarity	NPC476765
0.7895	Intermediate Similarity	NPC175351
0.7895	Intermediate Similarity	NPC121402
0.7895	Intermediate Similarity	NPC224356
0.7895	Intermediate Similarity	NPC476253
0.7895	Intermediate Similarity	NPC132753
0.7895	Intermediate Similarity	NPC151681
0.7872	Intermediate Similarity	NPC295347
0.7872	Intermediate Similarity	NPC472441
0.7872	Intermediate Similarity	NPC183012
0.7865	Intermediate Similarity	NPC472442
0.7865	Intermediate Similarity	NPC52628
0.7849	Intermediate Similarity	NPC472812
0.7849	Intermediate Similarity	NPC139692
0.7841	Intermediate Similarity	NPC311070
0.7841	Intermediate Similarity	NPC193198
0.7835	Intermediate Similarity	NPC472643
0.7826	Intermediate Similarity	NPC472642
0.7826	Intermediate Similarity	NPC472307
0.7816	Intermediate Similarity	NPC40228
0.7816	Intermediate Similarity	NPC229584
0.7816	Intermediate Similarity	NPC14203
0.7812	Intermediate Similarity	NPC23364
0.7802	Intermediate Similarity	NPC226863
0.7802	Intermediate Similarity	NPC474629
0.7791	Intermediate Similarity	NPC17550
0.7791	Intermediate Similarity	NPC150646
0.7789	Intermediate Similarity	NPC476797
0.7789	Intermediate Similarity	NPC112654
0.7789	Intermediate Similarity	NPC319692
0.7789	Intermediate Similarity	NPC325960
0.7789	Intermediate Similarity	NPC242848
0.7789	Intermediate Similarity	NPC134072
0.7789	Intermediate Similarity	NPC162346
0.7789	Intermediate Similarity	NPC234993
0.7766	Intermediate Similarity	NPC53685
0.7766	Intermediate Similarity	NPC96541
0.7766	Intermediate Similarity	NPC184870
0.7766	Intermediate Similarity	NPC470255
0.7765	Intermediate Similarity	NPC473756
0.7755	Intermediate Similarity	NPC58329
0.7755	Intermediate Similarity	NPC295791
0.7753	Intermediate Similarity	NPC30486
0.7753	Intermediate Similarity	NPC471302
0.7753	Intermediate Similarity	NPC471301
0.7745	Intermediate Similarity	NPC476766
0.7745	Intermediate Similarity	NPC235014
0.7742	Intermediate Similarity	NPC78594
0.7742	Intermediate Similarity	NPC233345
0.7742	Intermediate Similarity	NPC186363
0.7738	Intermediate Similarity	NPC476795
0.7732	Intermediate Similarity	NPC474012
0.7732	Intermediate Similarity	NPC476299
0.7727	Intermediate Similarity	NPC471298
0.7727	Intermediate Similarity	NPC186276
0.7727	Intermediate Similarity	NPC471296
0.7708	Intermediate Similarity	NPC204054
0.7708	Intermediate Similarity	NPC257726
0.7708	Intermediate Similarity	NPC53844
0.7708	Intermediate Similarity	NPC76266
0.7708	Intermediate Similarity	NPC477718
0.7708	Intermediate Similarity	NPC477719
0.7701	Intermediate Similarity	NPC271104
0.7684	Intermediate Similarity	NPC293052
0.7684	Intermediate Similarity	NPC209355
0.7677	Intermediate Similarity	NPC159533
0.7674	Intermediate Similarity	NPC239098
0.7667	Intermediate Similarity	NPC329630
0.7667	Intermediate Similarity	NPC30984
0.7667	Intermediate Similarity	NPC217394
0.7667	Intermediate Similarity	NPC253604
0.766	Intermediate Similarity	NPC271652
0.766	Intermediate Similarity	NPC472640
0.766	Intermediate Similarity	NPC472641
0.7647	Intermediate Similarity	NPC476759
0.7647	Intermediate Similarity	NPC263582
0.764	Intermediate Similarity	NPC321385
0.764	Intermediate Similarity	NPC471297
0.764	Intermediate Similarity	NPC215893
0.764	Intermediate Similarity	NPC472377
0.764	Intermediate Similarity	NPC97913
0.7634	Intermediate Similarity	NPC477147
0.7634	Intermediate Similarity	NPC477149
0.7609	Intermediate Similarity	NPC472302
0.7609	Intermediate Similarity	NPC24816
0.7609	Intermediate Similarity	NPC472378
0.7609	Intermediate Similarity	NPC196407
0.7609	Intermediate Similarity	NPC277771
0.7604	Intermediate Similarity	NPC29952
0.7604	Intermediate Similarity	NPC7124
0.7604	Intermediate Similarity	NPC165632
0.7586	Intermediate Similarity	NPC327674
0.7586	Intermediate Similarity	NPC242767
0.7586	Intermediate Similarity	NPC308038
0.7582	Intermediate Similarity	NPC322159
0.7582	Intermediate Similarity	NPC471219
0.7579	Intermediate Similarity	NPC250075
0.7579	Intermediate Similarity	NPC471720
0.7576	Intermediate Similarity	NPC165250
0.7576	Intermediate Similarity	NPC476769
0.7558	Intermediate Similarity	NPC97377
0.7558	Intermediate Similarity	NPC61952
0.7556	Intermediate Similarity	NPC165064
0.7556	Intermediate Similarity	NPC32223
0.7556	Intermediate Similarity	NPC472865
0.7556	Intermediate Similarity	NPC164577
0.7553	Intermediate Similarity	NPC329842
0.7553	Intermediate Similarity	NPC252433
0.7553	Intermediate Similarity	NPC303697
0.7553	Intermediate Similarity	NPC470113
0.7553	Intermediate Similarity	NPC324157
0.7551	Intermediate Similarity	NPC201406
0.7551	Intermediate Similarity	NPC477716
0.7551	Intermediate Similarity	NPC477721
0.7551	Intermediate Similarity	NPC117685
0.7551	Intermediate Similarity	NPC54705
0.7551	Intermediate Similarity	NPC324841
0.7549	Intermediate Similarity	NPC177524
0.7549	Intermediate Similarity	NPC392
0.7549	Intermediate Similarity	NPC219900
0.7527	Intermediate Similarity	NPC214387
0.7527	Intermediate Similarity	NPC50488
0.7527	Intermediate Similarity	NPC474396
0.7526	Intermediate Similarity	NPC474343
0.7526	Intermediate Similarity	NPC121339
0.7526	Intermediate Similarity	NPC253826
0.75	Intermediate Similarity	NPC471915
0.75	Intermediate Similarity	NPC35656

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 NPC474062 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1764
0.2-0.3	3950
0.3-0.4	2229
0.4-0.5	627
0.5-0.6	310
0.6-0.7	104
0.7-0.8	4
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
0.7931	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD6686	Approved
0.7473	Intermediate Similarity	NPD1694	Approved
0.7363	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7639	Approved
0.72	Intermediate Similarity	NPD7640	Approved
0.7143	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7638	Approved
0.7059	Intermediate Similarity	NPD7632	Discontinued
0.7021	Intermediate Similarity	NPD7521	Approved
0.7021	Intermediate Similarity	NPD6409	Approved
0.7021	Intermediate Similarity	NPD7334	Approved
0.7021	Intermediate Similarity	NPD5330	Approved
0.7021	Intermediate Similarity	NPD7146	Approved
0.7021	Intermediate Similarity	NPD6684	Approved
0.7	Intermediate Similarity	NPD6084	Phase 2
0.7	Intermediate Similarity	NPD6083	Phase 2
0.6989	Remote Similarity	NPD3133	Approved
0.6989	Remote Similarity	NPD3666	Approved
0.6989	Remote Similarity	NPD3665	Phase 1
0.697	Remote Similarity	NPD5695	Phase 3
0.6931	Remote Similarity	NPD4225	Approved
0.6916	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3617	Approved
0.6875	Remote Similarity	NPD5737	Approved
0.6875	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6672	Approved
0.6875	Remote Similarity	NPD6903	Approved
0.6869	Remote Similarity	NPD7748	Approved
0.6842	Remote Similarity	NPD4623	Approved
0.6842	Remote Similarity	NPD3618	Phase 1
0.6842	Remote Similarity	NPD4519	Discontinued
0.6837	Remote Similarity	NPD5693	Phase 1
0.6837	Remote Similarity	NPD7515	Phase 2
0.6792	Remote Similarity	NPD6412	Phase 2
0.6774	Remote Similarity	NPD3667	Approved
0.6768	Remote Similarity	NPD6399	Phase 3
0.6765	Remote Similarity	NPD5696	Approved
0.6742	Remote Similarity	NPD8039	Approved
0.6696	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6636	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4753	Phase 2
0.6633	Remote Similarity	NPD5328	Approved
0.6632	Remote Similarity	NPD4786	Approved
0.6596	Remote Similarity	NPD4221	Approved
0.6596	Remote Similarity	NPD4223	Phase 3
0.6566	Remote Similarity	NPD5785	Approved
0.6542	Remote Similarity	NPD5739	Approved
0.6542	Remote Similarity	NPD6675	Approved
0.6542	Remote Similarity	NPD6402	Approved
0.6542	Remote Similarity	NPD7128	Approved
0.6538	Remote Similarity	NPD6404	Discontinued
0.6531	Remote Similarity	NPD5208	Approved
0.6514	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5281	Approved
0.65	Remote Similarity	NPD5284	Approved
0.65	Remote Similarity	NPD6079	Approved
0.65	Remote Similarity	NPD7319	Approved
0.6486	Remote Similarity	NPD6882	Approved
0.6481	Remote Similarity	NPD5697	Approved
0.6481	Remote Similarity	NPD5701	Approved
0.6471	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6080	Approved
0.6465	Remote Similarity	NPD6673	Approved
0.6465	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6904	Approved
0.6458	Remote Similarity	NPD4197	Approved
0.6436	Remote Similarity	NPD4202	Approved
0.6436	Remote Similarity	NPD5778	Approved
0.6436	Remote Similarity	NPD5779	Approved
0.6429	Remote Similarity	NPD3573	Approved
0.6422	Remote Similarity	NPD6899	Approved
0.6422	Remote Similarity	NPD7320	Approved
0.6422	Remote Similarity	NPD6881	Approved
0.6422	Remote Similarity	NPD6011	Approved
0.64	Remote Similarity	NPD5207	Approved
0.64	Remote Similarity	NPD5692	Phase 3
0.6392	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD1696	Phase 3
0.6392	Remote Similarity	NPD5329	Approved
0.6383	Remote Similarity	NPD4695	Discontinued
0.6373	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7900	Approved
0.6364	Remote Similarity	NPD6373	Approved
0.6364	Remote Similarity	NPD6014	Approved
0.6364	Remote Similarity	NPD6012	Approved
0.6364	Remote Similarity	NPD6372	Approved
0.6364	Remote Similarity	NPD6013	Approved
0.6348	Remote Similarity	NPD7327	Approved
0.6348	Remote Similarity	NPD7328	Approved
0.6344	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6053	Discontinued
0.6337	Remote Similarity	NPD5694	Approved
0.6337	Remote Similarity	NPD6411	Approved
0.6337	Remote Similarity	NPD6050	Approved
0.6327	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5690	Phase 2
0.6327	Remote Similarity	NPD4694	Approved
0.6327	Remote Similarity	NPD6098	Approved
0.6327	Remote Similarity	NPD4689	Approved
0.6327	Remote Similarity	NPD4688	Approved
0.6327	Remote Similarity	NPD4690	Approved
0.6327	Remote Similarity	NPD5205	Approved
0.6327	Remote Similarity	NPD4693	Phase 3
0.6327	Remote Similarity	NPD4138	Approved
0.6327	Remote Similarity	NPD5280	Approved
0.6316	Remote Similarity	NPD4139	Approved
0.6316	Remote Similarity	NPD4692	Approved
0.6311	Remote Similarity	NPD5210	Approved
0.6311	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4629	Approved
0.6306	Remote Similarity	NPD6883	Approved
0.6306	Remote Similarity	NPD7290	Approved
0.6306	Remote Similarity	NPD7102	Approved
0.63	Remote Similarity	NPD6051	Approved
0.6293	Remote Similarity	NPD7516	Approved
0.6283	Remote Similarity	NPD8133	Approved
0.6262	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD4697	Phase 3
0.625	Remote Similarity	NPD5222	Approved
0.625	Remote Similarity	NPD6649	Approved
0.625	Remote Similarity	NPD5221	Approved
0.625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8130	Phase 1
0.625	Remote Similarity	NPD6847	Approved
0.625	Remote Similarity	NPD6617	Approved
0.625	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6869	Approved
0.625	Remote Similarity	NPD6650	Approved
0.6239	Remote Similarity	NPD8377	Approved
0.6239	Remote Similarity	NPD8294	Approved
0.6238	Remote Similarity	NPD46	Approved
0.6238	Remote Similarity	NPD6698	Approved
0.6214	Remote Similarity	NPD6001	Approved
0.6196	Remote Similarity	NPD3702	Approved
0.6195	Remote Similarity	NPD8297	Approved
0.619	Remote Similarity	NPD4755	Approved
0.619	Remote Similarity	NPD5173	Approved
0.6186	Remote Similarity	NPD5362	Discontinued
0.6186	Remote Similarity	NPD7154	Phase 3
0.6186	Remote Similarity	NPD8296	Approved
0.6186	Remote Similarity	NPD4788	Approved
0.6186	Remote Similarity	NPD8378	Approved
0.6186	Remote Similarity	NPD7503	Approved
0.6186	Remote Similarity	NPD8380	Approved
0.6186	Remote Similarity	NPD8335	Approved
0.6186	Remote Similarity	NPD8379	Approved
0.6186	Remote Similarity	NPD8033	Approved
0.6176	Remote Similarity	NPD8034	Phase 2
0.6176	Remote Similarity	NPD7637	Suspended
0.6176	Remote Similarity	NPD8035	Phase 2
0.6154	Remote Similarity	NPD5654	Approved
0.6147	Remote Similarity	NPD5141	Approved
0.6139	Remote Similarity	NPD6101	Approved
0.6139	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD3668	Phase 3
0.6121	Remote Similarity	NPD6009	Approved
0.6121	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD7614	Phase 1
0.6092	Remote Similarity	NPD7341	Phase 2
0.6092	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD8328	Phase 3
0.6075	Remote Similarity	NPD5286	Approved
0.6075	Remote Similarity	NPD4700	Approved
0.6075	Remote Similarity	NPD4696	Approved
0.6075	Remote Similarity	NPD5285	Approved
0.6066	Remote Similarity	NPD8293	Discontinued
0.6061	Remote Similarity	NPD5363	Approved
0.6048	Remote Similarity	NPD6914	Discontinued
0.6038	Remote Similarity	NPD5959	Approved
0.6034	Remote Similarity	NPD6274	Approved
0.6034	Remote Similarity	NPD6868	Approved
0.6023	Remote Similarity	NPD4224	Phase 2
0.6019	Remote Similarity	NPD5223	Approved
0.6018	Remote Similarity	NPD6371	Approved
0.6016	Remote Similarity	NPD7736	Approved
0.6	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD6370	Approved
0.6	Remote Similarity	NPD4137	Phase 3
0.5983	Remote Similarity	NPD6317	Approved
0.5981	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5224	Approved
0.5963	Remote Similarity	NPD5225	Approved
0.5963	Remote Similarity	NPD4633	Approved
0.5963	Remote Similarity	NPD5226	Approved
0.5962	Remote Similarity	NPD5133	Approved
0.5957	Remote Similarity	NPD6117	Approved
0.5957	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6067	Discontinued
0.5946	Remote Similarity	NPD6008	Approved
0.5943	Remote Similarity	NPD7732	Phase 3
0.5938	Remote Similarity	NPD4195	Approved
0.5934	Remote Similarity	NPD4691	Approved
0.5934	Remote Similarity	NPD4747	Approved
0.5932	Remote Similarity	NPD6335	Approved
0.5932	Remote Similarity	NPD6314	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