NPASS Compound

Structure

NPC471302 OpenBabel07101719252D 29 30 0 0 1 0 0 0 0 0999 V2000 -3.6720 -2.4867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8043 0.7514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3220 -1.3220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1297 -2.1600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1729 -0.6172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0405 -3.8553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6762 0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8572 -1.3015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2381 -0.8677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2910 -2.9205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7248 -4.5396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6191 -0.4338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6762 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9348 0.2505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0064 -3.3857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6067 -2.2362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5538 -0.1834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6596 -4.2891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9728 -3.4363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4117 -4.8982 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8381 -0.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -8.5819 -2.6842 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3610 -5.8646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1263 -0.9595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2233 -4.3711 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 4 24 1 0 0 0 0 5 24 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 13 1 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 2 0 0 0 0 11 18 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 20 25 1 0 0 0 0 21 23 1 0 0 0 0 22 26 2 0 0 0 0 22 29 1 0 0 0 0 23 27 1 0 0 0 0 23 29 1 0 0 0 0 24 25 1 0 0 0 0 25 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.28
Volume:	445.822
LogP:	5.444
LogD:	4.753
LogS:	-4.323
# Rotatable Bonds:	9
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.408
Synthetic Accessibility Score:	4.233
Fsp3:	0.6
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:	-5.056
MDCK Permeability:	2.1292331439326517e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.786
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.133
Plasma Protein Binding (PPB):	94.23249816894531%
Volume Distribution (VD):	0.863
Pgp-substrate:	1.3965553045272827%

ADMET: Metabolism

CYP1A2-inhibitor:	0.111
CYP1A2-substrate:	0.496
CYP2C19-inhibitor:	0.176
CYP2C19-substrate:	0.155
CYP2C9-inhibitor:	0.616
CYP2C9-substrate:	0.98
CYP2D6-inhibitor:	0.479
CYP2D6-substrate:	0.869
CYP3A4-inhibitor:	0.168
CYP3A4-substrate:	0.121

ADMET: Excretion

Clearance (CL):	4.154
Half-life (T1/2):	0.327

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.165
Drug-inuced Liver Injury (DILI):	0.013
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.547
Skin Sensitization:	0.718
Carcinogencity:	0.051
Eye Corrosion:	0.003
Eye Irritation:	0.109
Respiratory Toxicity:	0.396

Download Data

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

Natural Product: NPC471302

Natural Product ID:	NPC471302
*Common Name:**	Thorectidaeolide D
IUPAC Name:	2-hydroxy-3-[(3E,7E)-10-(1-hydroxy-2,2-dimethyl-6-methylidenecyclohexyl)-4,8-dimethyldeca-3,7-dienyl]-2H-furan-5-one
Synonyms:
Standard InCHIKey:	LQWPUSJIVMTIIO-QZPYEDBESA-N
Standard InCHI:	InChI=1S/C25H38O4/c1-18(11-7-13-21-17-22(26)29-23(21)27)9-6-10-19(2)14-16-25(28)20(3)12-8-15-24(25,4)5/h10-11,17,23,27-28H,3,6-9,12-16H2,1-2,4-5H3/b18-11+,19-10+
SMILES:	CC(=CCCC1=CC(=O)OC1O)CCC=C(C)CCC2(C(=C)CCCC2(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409160
PubChem CID:	72189181
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO33221	hyrtios communis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23944963]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[507568]
NPT396	Cell Line	T47D	Homo sapiens	IC50	>	10000.0	nM	PMID[507568]

☑ 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 NPC471302 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	158
0.1-0.2	1148
0.2-0.3	4847
0.3-0.4	13841
0.4-0.5	10472
0.5-0.6	7859
0.6-0.7	3748
0.7-0.8	577
0.8-0.85	33
0.85-0.9	13
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC471297
0.9259	High Similarity	NPC471301
0.925	High Similarity	NPC471298
0.8861	High Similarity	NPC473756
0.8824	High Similarity	NPC472809
0.8824	High Similarity	NPC472810
0.878	High Similarity	NPC323251
0.8736	High Similarity	NPC472811
0.8721	High Similarity	NPC470734
0.869	High Similarity	NPC42586
0.869	High Similarity	NPC473251
0.8659	High Similarity	NPC475944
0.8652	High Similarity	NPC472441
0.8636	High Similarity	NPC472812
0.8605	High Similarity	NPC474629
0.8571	High Similarity	NPC126518
0.8554	High Similarity	NPC324170
0.8539	High Similarity	NPC469697
0.8539	High Similarity	NPC104925
0.8539	High Similarity	NPC298973
0.8523	High Similarity	NPC477122
0.8478	Intermediate Similarity	NPC324841
0.8471	Intermediate Similarity	NPC472442
0.8471	Intermediate Similarity	NPC163606
0.8471	Intermediate Similarity	NPC474860
0.8471	Intermediate Similarity	NPC471300
0.8452	Intermediate Similarity	NPC474809
0.8409	Intermediate Similarity	NPC477782
0.8352	Intermediate Similarity	NPC162346
0.8333	Intermediate Similarity	NPC471296
0.8333	Intermediate Similarity	NPC324078
0.8333	Intermediate Similarity	NPC470255
0.8315	Intermediate Similarity	NPC477783
0.8315	Intermediate Similarity	NPC329842
0.8293	Intermediate Similarity	NPC474816
0.8293	Intermediate Similarity	NPC209135
0.8261	Intermediate Similarity	NPC477718
0.8261	Intermediate Similarity	NPC477719
0.8235	Intermediate Similarity	NPC472440
0.8235	Intermediate Similarity	NPC311070
0.8202	Intermediate Similarity	NPC78973
0.8182	Intermediate Similarity	NPC472378
0.8171	Intermediate Similarity	NPC262747
0.8161	Intermediate Similarity	NPC131813
0.8125	Intermediate Similarity	NPC476489
0.8125	Intermediate Similarity	NPC476490
0.8105	Intermediate Similarity	NPC472815
0.809	Intermediate Similarity	NPC251528
0.8085	Intermediate Similarity	NPC477716
0.8085	Intermediate Similarity	NPC477721
0.8065	Intermediate Similarity	NPC475709
0.8046	Intermediate Similarity	NPC329630
0.8046	Intermediate Similarity	NPC473659
0.8046	Intermediate Similarity	NPC475860
0.8046	Intermediate Similarity	NPC474694
0.8043	Intermediate Similarity	NPC13924
0.8023	Intermediate Similarity	NPC476927
0.8023	Intermediate Similarity	NPC42476
0.8022	Intermediate Similarity	NPC53555
0.8	Intermediate Similarity	NPC477717
0.8	Intermediate Similarity	NPC232426
0.8	Intermediate Similarity	NPC281942
0.7979	Intermediate Similarity	NPC473154
0.7979	Intermediate Similarity	NPC474440
0.7957	Intermediate Similarity	NPC470801
0.7935	Intermediate Similarity	NPC474554
0.7935	Intermediate Similarity	NPC105490
0.7931	Intermediate Similarity	NPC474693
0.7931	Intermediate Similarity	NPC470800
0.7912	Intermediate Similarity	NPC141831
0.7907	Intermediate Similarity	NPC2524
0.7895	Intermediate Similarity	NPC477720
0.7882	Intermediate Similarity	NPC10636
0.7879	Intermediate Similarity	NPC38948
0.7865	Intermediate Similarity	NPC166857
0.7849	Intermediate Similarity	NPC476488
0.7849	Intermediate Similarity	NPC476487
0.7849	Intermediate Similarity	NPC276110
0.7841	Intermediate Similarity	NPC471795
0.7841	Intermediate Similarity	NPC30984
0.7835	Intermediate Similarity	NPC120009
0.7826	Intermediate Similarity	NPC7349
0.7816	Intermediate Similarity	NPC23748
0.7816	Intermediate Similarity	NPC472377
0.78	Intermediate Similarity	NPC206618
0.7791	Intermediate Similarity	NPC170303
0.7778	Intermediate Similarity	NPC475074
0.7766	Intermediate Similarity	NPC17578
0.7766	Intermediate Similarity	NPC240673
0.7766	Intermediate Similarity	NPC165632
0.7765	Intermediate Similarity	NPC242767
0.7753	Intermediate Similarity	NPC471219
0.7753	Intermediate Similarity	NPC474062
0.7753	Intermediate Similarity	NPC211892
0.7742	Intermediate Similarity	NPC475572
0.7742	Intermediate Similarity	NPC474555
0.7727	Intermediate Similarity	NPC474865
0.7727	Intermediate Similarity	NPC31086
0.7717	Intermediate Similarity	NPC78594
0.7708	Intermediate Similarity	NPC38855
0.7708	Intermediate Similarity	NPC472826
0.7708	Intermediate Similarity	NPC16601
0.7701	Intermediate Similarity	NPC256112
0.7701	Intermediate Similarity	NPC471218
0.7692	Intermediate Similarity	NPC5509
0.7692	Intermediate Similarity	NPC174342
0.7684	Intermediate Similarity	NPC98112
0.7683	Intermediate Similarity	NPC222244
0.7683	Intermediate Similarity	NPC16349
0.7677	Intermediate Similarity	NPC239961
0.7674	Intermediate Similarity	NPC281880
0.7667	Intermediate Similarity	NPC471796
0.7667	Intermediate Similarity	NPC475678
0.7667	Intermediate Similarity	NPC312561
0.7654	Intermediate Similarity	NPC4299
0.7653	Intermediate Similarity	NPC45897
0.7653	Intermediate Similarity	NPC471938
0.7647	Intermediate Similarity	NPC184737
0.764	Intermediate Similarity	NPC217394
0.764	Intermediate Similarity	NPC106416
0.764	Intermediate Similarity	NPC253604
0.764	Intermediate Similarity	NPC35933
0.764	Intermediate Similarity	NPC86316
0.764	Intermediate Similarity	NPC65661
0.764	Intermediate Similarity	NPC474013
0.764	Intermediate Similarity	NPC471494
0.7634	Intermediate Similarity	NPC472303
0.7634	Intermediate Similarity	NPC152778
0.7634	Intermediate Similarity	NPC205034
0.7634	Intermediate Similarity	NPC162615
0.7634	Intermediate Similarity	NPC139692
0.7634	Intermediate Similarity	NPC472640
0.7634	Intermediate Similarity	NPC242069
0.7634	Intermediate Similarity	NPC156553
0.7634	Intermediate Similarity	NPC472641
0.7629	Intermediate Similarity	NPC471075
0.7629	Intermediate Similarity	NPC198992
0.7619	Intermediate Similarity	NPC477202
0.7614	Intermediate Similarity	NPC477124
0.7614	Intermediate Similarity	NPC30502
0.7614	Intermediate Similarity	NPC49208
0.7609	Intermediate Similarity	NPC51486
0.7609	Intermediate Similarity	NPC209816
0.7609	Intermediate Similarity	NPC310479
0.7609	Intermediate Similarity	NPC472642
0.7609	Intermediate Similarity	NPC469403
0.7609	Intermediate Similarity	NPC280149
0.7609	Intermediate Similarity	NPC182136
0.7609	Intermediate Similarity	NPC221111
0.7604	Intermediate Similarity	NPC278673
0.7604	Intermediate Similarity	NPC275086
0.7604	Intermediate Similarity	NPC325229
0.76	Intermediate Similarity	NPC471205
0.7586	Intermediate Similarity	NPC159148
0.7582	Intermediate Similarity	NPC93411
0.7579	Intermediate Similarity	NPC242848
0.7579	Intermediate Similarity	NPC473153
0.7579	Intermediate Similarity	NPC134072
0.7579	Intermediate Similarity	NPC234993
0.7579	Intermediate Similarity	NPC16967
0.7576	Intermediate Similarity	NPC471937
0.7556	Intermediate Similarity	NPC175145
0.7556	Intermediate Similarity	NPC475069
0.7556	Intermediate Similarity	NPC311163
0.7553	Intermediate Similarity	NPC477722
0.7553	Intermediate Similarity	NPC57117
0.7551	Intermediate Similarity	NPC121423
0.7551	Intermediate Similarity	NPC109195
0.7551	Intermediate Similarity	NPC475038
0.7551	Intermediate Similarity	NPC471914
0.7531	Intermediate Similarity	NPC101622
0.7529	Intermediate Similarity	NPC477203
0.7529	Intermediate Similarity	NPC132542
0.7528	Intermediate Similarity	NPC78673
0.7528	Intermediate Similarity	NPC306951
0.7528	Intermediate Similarity	NPC160517
0.7528	Intermediate Similarity	NPC186155
0.7528	Intermediate Similarity	NPC475706
0.7528	Intermediate Similarity	NPC96055
0.7527	Intermediate Similarity	NPC72845
0.7527	Intermediate Similarity	NPC472814
0.7527	Intermediate Similarity	NPC177037
0.7527	Intermediate Similarity	NPC179517
0.7527	Intermediate Similarity	NPC249034
0.7527	Intermediate Similarity	NPC289479
0.7527	Intermediate Similarity	NPC165904
0.7526	Intermediate Similarity	NPC477972
0.7526	Intermediate Similarity	NPC228251
0.7526	Intermediate Similarity	NPC219285
0.7526	Intermediate Similarity	NPC161527
0.7526	Intermediate Similarity	NPC477971
0.7526	Intermediate Similarity	NPC20113
0.7526	Intermediate Similarity	NPC476767
0.7526	Intermediate Similarity	NPC477968
0.7525	Intermediate Similarity	NPC470024
0.75	Intermediate Similarity	NPC218158
0.75	Intermediate Similarity	NPC50488
0.75	Intermediate Similarity	NPC472266
0.75	Intermediate Similarity	NPC51499
0.75	Intermediate Similarity	NPC474396

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 NPC471302 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	135
0.1-0.2	1504
0.2-0.3	3983
0.3-0.4	2501
0.4-0.5	637
0.5-0.6	311
0.6-0.7	75
0.7-0.8	3
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD6400	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6686	Approved
0.7347	Intermediate Similarity	NPD7640	Approved
0.7347	Intermediate Similarity	NPD7639	Approved
0.7303	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7638	Approved
0.7245	Intermediate Similarity	NPD4225	Approved
0.7064	Intermediate Similarity	NPD7327	Approved
0.7064	Intermediate Similarity	NPD7328	Approved
0.7037	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7516	Approved
0.6937	Remote Similarity	NPD8294	Approved
0.6937	Remote Similarity	NPD8377	Approved
0.6931	Remote Similarity	NPD5344	Discontinued
0.6875	Remote Similarity	NPD8380	Approved
0.6875	Remote Similarity	NPD8379	Approved
0.6875	Remote Similarity	NPD5785	Approved
0.6875	Remote Similarity	NPD8378	Approved
0.6875	Remote Similarity	NPD8296	Approved
0.6875	Remote Similarity	NPD8335	Approved
0.6875	Remote Similarity	NPD8033	Approved
0.6804	Remote Similarity	NPD7637	Suspended
0.6771	Remote Similarity	NPD6051	Approved
0.6733	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7503	Approved
0.6707	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD8039	Approved
0.6702	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6695	Phase 3
0.6638	Remote Similarity	NPD7507	Approved
0.6634	Remote Similarity	NPD6084	Phase 2
0.6634	Remote Similarity	NPD6083	Phase 2
0.6596	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD46	Approved
0.6531	Remote Similarity	NPD6698	Approved
0.6526	Remote Similarity	NPD1694	Approved
0.6522	Remote Similarity	NPD4822	Approved
0.6522	Remote Similarity	NPD4821	Approved
0.6522	Remote Similarity	NPD4819	Approved
0.6522	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4820	Approved
0.6518	Remote Similarity	NPD7115	Discovery
0.65	Remote Similarity	NPD7748	Approved
0.6489	Remote Similarity	NPD7154	Phase 3
0.6489	Remote Similarity	NPD5362	Discontinued
0.6484	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7319	Approved
0.6465	Remote Similarity	NPD7515	Phase 2
0.6463	Remote Similarity	NPD4194	Approved
0.6463	Remote Similarity	NPD4193	Approved
0.6463	Remote Similarity	NPD4191	Approved
0.6463	Remote Similarity	NPD4192	Approved
0.6436	Remote Similarity	NPD5695	Phase 3
0.6404	Remote Similarity	NPD6924	Approved
0.6404	Remote Similarity	NPD6926	Approved
0.6392	Remote Similarity	NPD7750	Discontinued
0.6392	Remote Similarity	NPD7524	Approved
0.6383	Remote Similarity	NPD5209	Approved
0.6373	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7838	Discovery
0.6355	Remote Similarity	NPD7128	Approved
0.6355	Remote Similarity	NPD6675	Approved
0.6355	Remote Similarity	NPD6402	Approved
0.6355	Remote Similarity	NPD5739	Approved
0.6354	Remote Similarity	NPD5363	Approved
0.6344	Remote Similarity	NPD6930	Phase 2
0.6344	Remote Similarity	NPD6931	Approved
0.6344	Remote Similarity	NPD7514	Phase 3
0.6344	Remote Similarity	NPD7332	Phase 2
0.6344	Remote Similarity	NPD7525	Registered
0.633	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6672	Approved
0.6327	Remote Similarity	NPD5737	Approved
0.6316	Remote Similarity	NPD5332	Approved
0.6316	Remote Similarity	NPD5331	Approved
0.6311	Remote Similarity	NPD7902	Approved
0.6306	Remote Similarity	NPD6882	Approved
0.6304	Remote Similarity	NPD4271	Approved
0.6304	Remote Similarity	NPD4268	Approved
0.63	Remote Similarity	NPD5693	Phase 1
0.6296	Remote Similarity	NPD6412	Phase 2
0.6289	Remote Similarity	NPD6409	Approved
0.6289	Remote Similarity	NPD7334	Approved
0.6289	Remote Similarity	NPD6684	Approved
0.6289	Remote Similarity	NPD5330	Approved
0.6289	Remote Similarity	NPD7146	Approved
0.6289	Remote Similarity	NPD7521	Approved
0.6277	Remote Similarity	NPD4790	Discontinued
0.6275	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6371	Approved
0.6265	Remote Similarity	NPD368	Approved
0.6264	Remote Similarity	NPD6933	Approved
0.625	Remote Similarity	NPD5696	Approved
0.6239	Remote Similarity	NPD6881	Approved
0.6239	Remote Similarity	NPD6899	Approved
0.6239	Remote Similarity	NPD7320	Approved
0.6238	Remote Similarity	NPD6399	Phase 3
0.6238	Remote Similarity	NPD5779	Approved
0.6238	Remote Similarity	NPD5778	Approved
0.6237	Remote Similarity	NPD6929	Approved
0.6211	Remote Similarity	NPD4269	Approved
0.6211	Remote Similarity	NPD4270	Approved
0.6196	Remote Similarity	NPD6925	Approved
0.6196	Remote Similarity	NPD5776	Phase 2
0.6186	Remote Similarity	NPD1696	Phase 3
0.6182	Remote Similarity	NPD6372	Approved
0.6182	Remote Similarity	NPD6373	Approved
0.6162	Remote Similarity	NPD6903	Approved
0.6162	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8264	Approved
0.6147	Remote Similarity	NPD5701	Approved
0.6147	Remote Similarity	NPD5697	Approved
0.6139	Remote Similarity	NPD7087	Discontinued
0.6139	Remote Similarity	NPD6411	Approved
0.6136	Remote Similarity	NPD6923	Approved
0.6136	Remote Similarity	NPD6922	Approved
0.6129	Remote Similarity	NPD7145	Approved
0.6126	Remote Similarity	NPD6883	Approved
0.6126	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7290	Approved
0.6126	Remote Similarity	NPD7102	Approved
0.6122	Remote Similarity	NPD5786	Approved
0.6122	Remote Similarity	NPD4623	Approved
0.6122	Remote Similarity	NPD4519	Discontinued
0.6122	Remote Similarity	NPD3618	Phase 1
0.6117	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6902	Approved
0.6105	Remote Similarity	NPD6898	Phase 1
0.6105	Remote Similarity	NPD5369	Approved
0.61	Remote Similarity	NPD5328	Approved
0.61	Remote Similarity	NPD4753	Phase 2
0.61	Remote Similarity	NPD6673	Approved
0.61	Remote Similarity	NPD6080	Approved
0.61	Remote Similarity	NPD6904	Approved
0.6091	Remote Similarity	NPD6011	Approved
0.6082	Remote Similarity	NPD3665	Phase 1
0.6082	Remote Similarity	NPD3133	Approved
0.6082	Remote Similarity	NPD3666	Approved
0.6071	Remote Similarity	NPD6869	Approved
0.6071	Remote Similarity	NPD6650	Approved
0.6071	Remote Similarity	NPD8130	Phase 1
0.6071	Remote Similarity	NPD6649	Approved
0.6071	Remote Similarity	NPD6847	Approved
0.6071	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6617	Approved
0.6067	Remote Similarity	NPD7143	Approved
0.6067	Remote Similarity	NPD7144	Approved
0.6064	Remote Similarity	NPD4195	Approved
0.6064	Remote Similarity	NPD7645	Phase 2
0.6061	Remote Similarity	NPD4251	Approved
0.6061	Remote Similarity	NPD4250	Approved
0.6058	Remote Similarity	NPD7839	Suspended
0.6042	Remote Similarity	NPD6435	Approved
0.6036	Remote Similarity	NPD6014	Approved
0.6036	Remote Similarity	NPD6012	Approved
0.6036	Remote Similarity	NPD6013	Approved
0.6022	Remote Similarity	NPD6932	Approved
0.602	Remote Similarity	NPD6893	Approved
0.6019	Remote Similarity	NPD6647	Phase 2
0.6019	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7900	Approved
0.6018	Remote Similarity	NPD6053	Discontinued
0.6018	Remote Similarity	NPD8297	Approved
0.6017	Remote Similarity	NPD8517	Approved
0.6017	Remote Similarity	NPD8513	Phase 3
0.6017	Remote Similarity	NPD8515	Approved
0.6017	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD7150	Approved
0.6	Remote Similarity	NPD4252	Approved
0.6	Remote Similarity	NPD7152	Approved
0.6	Remote Similarity	NPD7151	Approved
0.6	Remote Similarity	NPD7509	Discontinued
0.598	Remote Similarity	NPD6079	Approved
0.598	Remote Similarity	NPD5284	Approved
0.598	Remote Similarity	NPD5281	Approved
0.598	Remote Similarity	NPD6050	Approved
0.5978	Remote Similarity	NPD6942	Approved
0.5978	Remote Similarity	NPD7339	Approved
0.5977	Remote Similarity	NPD7331	Phase 2
0.5965	Remote Similarity	NPD8133	Approved
0.596	Remote Similarity	NPD4249	Approved
0.596	Remote Similarity	NPD5279	Phase 3
0.5941	Remote Similarity	NPD689	Discontinued
0.5941	Remote Similarity	NPD6101	Approved
0.5941	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5211	Phase 2
0.5922	Remote Similarity	NPD4202	Approved
0.5918	Remote Similarity	NPD4786	Approved
0.5914	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4211	Phase 1
0.5902	Remote Similarity	NPD8293	Discontinued
0.59	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.59	Remote Similarity	NPD3573	Approved
0.5895	Remote Similarity	NPD6683	Phase 2
0.5882	Remote Similarity	NPD5692	Phase 3
0.5876	Remote Similarity	NPD3667	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