NPASS Compound

Structure

CID240673 OpenBabel06191716042D 21 23 0 0 1 0 0 0 0 0999 V2000 1.3685 1.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6369 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6994 1.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 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 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4049 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 1.7601 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 16 1 0 0 0 0 3 16 1 0 0 0 0 5 20 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 6 0 0 0 11 16 1 0 0 0 0 11 17 1 1 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 20 1 1 0 0 0 15 21 1 0 0 0 0 17 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.18
Volume:	306.807
LogP:	3.598
LogD:	3.182
LogS:	-3.468
# Rotatable Bonds:	2
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.868
Synthetic Accessibility Score:	4.317
Fsp3:	0.765
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.666
MDCK Permeability:	2.4506069166818634e-05
Pgp-inhibitor:	0.042
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.296
Plasma Protein Binding (PPB):	93.54822540283203%
Volume Distribution (VD):	1.918
Pgp-substrate:	10.114487648010254%

ADMET: Metabolism

CYP1A2-inhibitor:	0.166
CYP1A2-substrate:	0.643
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.834
CYP2C9-inhibitor:	0.379
CYP2C9-substrate:	0.895
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.364
CYP3A4-inhibitor:	0.04
CYP3A4-substrate:	0.26

ADMET: Excretion

Clearance (CL):	9.277
Half-life (T1/2):	0.211

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.163
Drug-inuced Liver Injury (DILI):	0.686
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.919
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.569
Carcinogencity:	0.76
Eye Corrosion:	0.004
Eye Irritation:	0.28
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC240673

Natural Product ID:	NPC240673
*Common Name:**	Dendocarbin J
IUPAC Name:	(1S,4R,5aS,9aS)-1-ethoxy-4-hydroxy-6,6,9a-trimethyl-4,5,5a,7,8,9-hexahydro-1H-benzo[e][2]benzofuran-3-one
Synonyms:	Dendocarbin J
Standard InCHIKey:	XUUGSOPITUNJLM-XSAQDOAFSA-N
Standard InCHI:	InChI=1S/C17H26O4/c1-5-20-15-13-12(14(19)21-15)10(18)9-11-16(2,3)7-6-8-17(11,13)4/h10-11,15,18H,5-9H2,1-4H3/t10-,11+,15+,17+/m1/s1
SMILES:	CCO[C@@H]1C2=C([C@@H](C[C@H]3C(C)(C)CCC[C@]23C)O)C(=O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500860
PubChem CID:	10334643
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]
NPO7781	Piper scutifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18031016]
NPO6857	Actinidia eriantha	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8660	Dendrodoris carbunculosa	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO578	Eriope blanchetii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2429	Gracilariopsis lemaneiformis	Species	Gracilariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7781	Piper scutifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7474	Sicya macularia	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7919	Hedysarum sericeum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5987	Hypericum yojiroanum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6857	Actinidia eriantha	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1548	Nardia succulenta	Species	Solenostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24628	Lamium galeobdolon	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5268	Chenopodium hircinum	Species	Chenopodiaceae	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	=	17.0	ug.mL-1	PMID[541898]
NPT168	Cell Line	P388	Mus musculus	IC50	=	4.0	ug.mL-1	PMID[541898]
NPT168	Cell Line	P388	Mus musculus	IC50	=	11.0	ug.mL-1	PMID[541898]
NPT168	Cell Line	P388	Mus musculus	IC50	=	8.0	ug.mL-1	PMID[541898]

☑ 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 NPC240673 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	210
0.1-0.2	1324
0.2-0.3	4823
0.3-0.4	10086
0.4-0.5	12372
0.5-0.6	6773
0.6-0.7	5993
0.7-0.8	1034
0.8-0.85	60
0.85-0.9	15
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC17578
0.9775	High Similarity	NPC474554
0.9775	High Similarity	NPC474555
0.9362	High Similarity	NPC471075
0.9043	High Similarity	NPC475709
0.8989	High Similarity	NPC474062
0.8817	High Similarity	NPC115021
0.88	High Similarity	NPC300614
0.88	High Similarity	NPC90946
0.8764	High Similarity	NPC71626
0.8713	High Similarity	NPC31522
0.871	High Similarity	NPC141831
0.8696	High Similarity	NPC470734
0.8602	High Similarity	NPC281942
0.8602	High Similarity	NPC477782
0.8602	High Similarity	NPC232426
0.8542	High Similarity	NPC242848
0.8511	High Similarity	NPC472814
0.8511	High Similarity	NPC177037
0.8511	High Similarity	NPC477783
0.8469	Intermediate Similarity	NPC474012
0.8469	Intermediate Similarity	NPC476299
0.8454	Intermediate Similarity	NPC53844
0.8447	Intermediate Similarity	NPC235014
0.8431	Intermediate Similarity	NPC325054
0.84	Intermediate Similarity	NPC159533
0.8387	Intermediate Similarity	NPC472810
0.8387	Intermediate Similarity	NPC472809
0.8351	Intermediate Similarity	NPC476797
0.8333	Intermediate Similarity	NPC298973
0.8333	Intermediate Similarity	NPC104925
0.8316	Intermediate Similarity	NPC165904
0.8316	Intermediate Similarity	NPC179517
0.8298	Intermediate Similarity	NPC251528
0.8298	Intermediate Similarity	NPC5509
0.828	Intermediate Similarity	NPC312561
0.8269	Intermediate Similarity	NPC476766
0.8261	Intermediate Similarity	NPC473251
0.8261	Intermediate Similarity	NPC42586
0.8252	Intermediate Similarity	NPC476765
0.8229	Intermediate Similarity	NPC271652
0.8229	Intermediate Similarity	NPC139692
0.8229	Intermediate Similarity	NPC472812
0.8222	Intermediate Similarity	NPC282293
0.8218	Intermediate Similarity	NPC471208
0.8211	Intermediate Similarity	NPC472307
0.8211	Intermediate Similarity	NPC51486
0.8173	Intermediate Similarity	NPC476759
0.8163	Intermediate Similarity	NPC470801
0.8163	Intermediate Similarity	NPC234993
0.8163	Intermediate Similarity	NPC134072
0.8144	Intermediate Similarity	NPC469697
0.8144	Intermediate Similarity	NPC53685
0.8125	Intermediate Similarity	NPC472811
0.8119	Intermediate Similarity	NPC295791
0.8105	Intermediate Similarity	NPC174342
0.81	Intermediate Similarity	NPC117685
0.81	Intermediate Similarity	NPC477720
0.8081	Intermediate Similarity	NPC132753
0.8081	Intermediate Similarity	NPC224356
0.8081	Intermediate Similarity	NPC175351
0.8081	Intermediate Similarity	NPC151681
0.8081	Intermediate Similarity	NPC121402
0.8061	Intermediate Similarity	NPC472441
0.8041	Intermediate Similarity	NPC242069
0.8041	Intermediate Similarity	NPC472641
0.8041	Intermediate Similarity	NPC166346
0.8041	Intermediate Similarity	NPC472303
0.8041	Intermediate Similarity	NPC472640
0.8021	Intermediate Similarity	NPC161638
0.8021	Intermediate Similarity	NPC472642
0.8	Intermediate Similarity	NPC316598
0.8	Intermediate Similarity	NPC474440
0.8	Intermediate Similarity	NPC472378
0.8	Intermediate Similarity	NPC474629
0.7982	Intermediate Similarity	NPC474483
0.798	Intermediate Similarity	NPC154526
0.798	Intermediate Similarity	NPC472363
0.798	Intermediate Similarity	NPC112654
0.798	Intermediate Similarity	NPC162346
0.798	Intermediate Similarity	NPC472362
0.7978	Intermediate Similarity	NPC316500
0.7961	Intermediate Similarity	NPC296950
0.7961	Intermediate Similarity	NPC146731
0.7959	Intermediate Similarity	NPC475572
0.7959	Intermediate Similarity	NPC184870
0.7941	Intermediate Similarity	NPC134077
0.7941	Intermediate Similarity	NPC476890
0.7941	Intermediate Similarity	NPC58329
0.7941	Intermediate Similarity	NPC165250
0.7938	Intermediate Similarity	NPC65513
0.7938	Intermediate Similarity	NPC289479
0.7938	Intermediate Similarity	NPC477122
0.7921	Intermediate Similarity	NPC476767
0.7921	Intermediate Similarity	NPC477721
0.7921	Intermediate Similarity	NPC477716
0.7921	Intermediate Similarity	NPC54705
0.7921	Intermediate Similarity	NPC472644
0.7905	Intermediate Similarity	NPC392
0.7905	Intermediate Similarity	NPC219900
0.7905	Intermediate Similarity	NPC177524
0.79	Intermediate Similarity	NPC477719
0.79	Intermediate Similarity	NPC477718
0.79	Intermediate Similarity	NPC208094
0.7895	Intermediate Similarity	NPC171722
0.7885	Intermediate Similarity	NPC252296
0.7879	Intermediate Similarity	NPC476487
0.7879	Intermediate Similarity	NPC476488
0.7879	Intermediate Similarity	NPC209355
0.7879	Intermediate Similarity	NPC183012
0.7872	Intermediate Similarity	NPC65661
0.7872	Intermediate Similarity	NPC472442
0.7872	Intermediate Similarity	NPC474860
0.7872	Intermediate Similarity	NPC86316
0.7872	Intermediate Similarity	NPC471300
0.7872	Intermediate Similarity	NPC106416
0.7872	Intermediate Similarity	NPC189311
0.7864	Intermediate Similarity	NPC471364
0.7864	Intermediate Similarity	NPC476889
0.7864	Intermediate Similarity	NPC471365
0.7864	Intermediate Similarity	NPC132395
0.7857	Intermediate Similarity	NPC129434
0.7857	Intermediate Similarity	NPC476204
0.7857	Intermediate Similarity	NPC170084
0.7857	Intermediate Similarity	NPC469939
0.7849	Intermediate Similarity	NPC471297
0.7849	Intermediate Similarity	NPC472440
0.7849	Intermediate Similarity	NPC311070
0.7843	Intermediate Similarity	NPC63249
0.7843	Intermediate Similarity	NPC469657
0.7843	Intermediate Similarity	NPC477717
0.7843	Intermediate Similarity	NPC476888
0.7843	Intermediate Similarity	NPC93744
0.7843	Intermediate Similarity	NPC244456
0.7843	Intermediate Similarity	NPC472643
0.7835	Intermediate Similarity	NPC477149
0.7835	Intermediate Similarity	NPC477147
0.7835	Intermediate Similarity	NPC113393
0.7835	Intermediate Similarity	NPC78973
0.7835	Intermediate Similarity	NPC8062
0.7822	Intermediate Similarity	NPC473154
0.7812	Intermediate Similarity	NPC307298
0.7812	Intermediate Similarity	NPC226863
0.781	Intermediate Similarity	NPC475570
0.781	Intermediate Similarity	NPC184512
0.781	Intermediate Similarity	NPC91034
0.78	Intermediate Similarity	NPC165632
0.78	Intermediate Similarity	NPC7124
0.78	Intermediate Similarity	NPC202833
0.7789	Intermediate Similarity	NPC322159
0.7789	Intermediate Similarity	NPC198761
0.7789	Intermediate Similarity	NPC250981
0.7789	Intermediate Similarity	NPC131813
0.7788	Intermediate Similarity	NPC476763
0.7788	Intermediate Similarity	NPC476764
0.7788	Intermediate Similarity	NPC471937
0.7778	Intermediate Similarity	NPC470697
0.7778	Intermediate Similarity	NPC470255
0.7778	Intermediate Similarity	NPC96541
0.7778	Intermediate Similarity	NPC42658
0.7778	Intermediate Similarity	NPC84893
0.7768	Intermediate Similarity	NPC476127
0.7768	Intermediate Similarity	NPC476150
0.7767	Intermediate Similarity	NPC40918
0.7767	Intermediate Similarity	NPC471363
0.7767	Intermediate Similarity	NPC476081
0.7767	Intermediate Similarity	NPC472815
0.7767	Intermediate Similarity	NPC238397
0.7767	Intermediate Similarity	NPC471914
0.7766	Intermediate Similarity	NPC471302
0.7757	Intermediate Similarity	NPC472666
0.7755	Intermediate Similarity	NPC252433
0.7755	Intermediate Similarity	NPC329842
0.7755	Intermediate Similarity	NPC78594
0.7745	Intermediate Similarity	NPC469864
0.7745	Intermediate Similarity	NPC174314
0.7745	Intermediate Similarity	NPC470761
0.7745	Intermediate Similarity	NPC324841
0.7745	Intermediate Similarity	NPC469872
0.7745	Intermediate Similarity	NPC473219
0.7742	Intermediate Similarity	NPC471298
0.7736	Intermediate Similarity	NPC220155
0.7736	Intermediate Similarity	NPC473483
0.7732	Intermediate Similarity	NPC168131
0.7732	Intermediate Similarity	NPC214387
0.7727	Intermediate Similarity	NPC471816
0.7723	Intermediate Similarity	NPC121339
0.7723	Intermediate Similarity	NPC253826
0.7723	Intermediate Similarity	NPC476253
0.7714	Intermediate Similarity	NPC472645
0.7714	Intermediate Similarity	NPC476762
0.7714	Intermediate Similarity	NPC476761
0.7714	Intermediate Similarity	NPC476760
0.7714	Intermediate Similarity	NPC1679
0.7708	Intermediate Similarity	NPC220930
0.7708	Intermediate Similarity	NPC272039
0.7708	Intermediate Similarity	NPC475678
0.7706	Intermediate Similarity	NPC157441
0.77	Intermediate Similarity	NPC295347
0.77	Intermediate Similarity	NPC473369

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 NPC240673 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	1797
0.2-0.3	3744
0.3-0.4	2274
0.4-0.5	689
0.5-0.6	298
0.6-0.7	156
0.7-0.8	7
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
0.7905	Intermediate Similarity	NPD6686	Approved
0.7647	Intermediate Similarity	NPD4225	Approved
0.7579	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD7640	Approved
0.7404	Intermediate Similarity	NPD7639	Approved
0.7345	Intermediate Similarity	NPD7115	Discovery
0.732	Intermediate Similarity	NPD1694	Approved
0.7308	Intermediate Similarity	NPD7638	Approved
0.7273	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7632	Discontinued
0.725	Intermediate Similarity	NPD7319	Approved
0.7156	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD7507	Approved
0.7087	Intermediate Similarity	NPD7748	Approved
0.7059	Intermediate Similarity	NPD7515	Phase 2
0.7048	Intermediate Similarity	NPD6083	Phase 2
0.7048	Intermediate Similarity	NPD6084	Phase 2
0.7027	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5695	Phase 3
0.7	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6882	Approved
0.699	Remote Similarity	NPD5779	Approved
0.699	Remote Similarity	NPD5778	Approved
0.6961	Remote Similarity	NPD5785	Approved
0.6909	Remote Similarity	NPD7128	Approved
0.6909	Remote Similarity	NPD5739	Approved
0.6909	Remote Similarity	NPD6675	Approved
0.6909	Remote Similarity	NPD6402	Approved
0.69	Remote Similarity	NPD3618	Phase 1
0.69	Remote Similarity	NPD7334	Approved
0.69	Remote Similarity	NPD7521	Approved
0.69	Remote Similarity	NPD6409	Approved
0.69	Remote Similarity	NPD6684	Approved
0.69	Remote Similarity	NPD5330	Approved
0.69	Remote Similarity	NPD7146	Approved
0.6897	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6411	Approved
0.6887	Remote Similarity	NPD7902	Approved
0.6869	Remote Similarity	NPD3665	Phase 1
0.6869	Remote Similarity	NPD3133	Approved
0.6869	Remote Similarity	NPD3666	Approved
0.6857	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5701	Approved
0.6847	Remote Similarity	NPD5697	Approved
0.6838	Remote Similarity	NPD7328	Approved
0.6838	Remote Similarity	NPD7327	Approved
0.6833	Remote Similarity	NPD8328	Phase 3
0.6827	Remote Similarity	NPD6399	Phase 3
0.6822	Remote Similarity	NPD5696	Approved
0.6803	Remote Similarity	NPD8293	Discontinued
0.6786	Remote Similarity	NPD6881	Approved
0.6786	Remote Similarity	NPD7320	Approved
0.6786	Remote Similarity	NPD6899	Approved
0.678	Remote Similarity	NPD7516	Approved
0.6765	Remote Similarity	NPD6672	Approved
0.6765	Remote Similarity	NPD6903	Approved
0.6765	Remote Similarity	NPD5737	Approved
0.6765	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6370	Approved
0.6748	Remote Similarity	NPD7736	Approved
0.6733	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7637	Suspended
0.6731	Remote Similarity	NPD5693	Phase 1
0.6726	Remote Similarity	NPD6014	Approved
0.6726	Remote Similarity	NPD6373	Approved
0.6726	Remote Similarity	NPD6372	Approved
0.6726	Remote Similarity	NPD6013	Approved
0.6726	Remote Similarity	NPD6012	Approved
0.6723	Remote Similarity	NPD8377	Approved
0.6723	Remote Similarity	NPD8294	Approved
0.6699	Remote Similarity	NPD5328	Approved
0.6699	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4753	Phase 2
0.6699	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8378	Approved
0.6639	Remote Similarity	NPD7492	Approved
0.6638	Remote Similarity	NPD8133	Approved
0.6637	Remote Similarity	NPD6011	Approved
0.6636	Remote Similarity	NPD5211	Phase 2
0.6609	Remote Similarity	NPD6847	Approved
0.6609	Remote Similarity	NPD8130	Phase 1
0.6609	Remote Similarity	NPD6650	Approved
0.6609	Remote Similarity	NPD6617	Approved
0.6609	Remote Similarity	NPD6869	Approved
0.6609	Remote Similarity	NPD6649	Approved
0.6604	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7900	Approved
0.6598	Remote Similarity	NPD3617	Approved
0.6585	Remote Similarity	NPD6616	Approved
0.6583	Remote Similarity	NPD6059	Approved
0.6583	Remote Similarity	NPD6054	Approved
0.6574	Remote Similarity	NPD4755	Approved
0.6571	Remote Similarity	NPD6079	Approved
0.6569	Remote Similarity	NPD5279	Phase 3
0.6569	Remote Similarity	NPD4519	Discontinued
0.6569	Remote Similarity	NPD4623	Approved
0.6552	Remote Similarity	NPD6053	Discontinued
0.6552	Remote Similarity	NPD8297	Approved
0.6535	Remote Similarity	NPD4786	Approved
0.6532	Remote Similarity	NPD7078	Approved
0.6529	Remote Similarity	NPD6015	Approved
0.6529	Remote Similarity	NPD6016	Approved
0.6522	Remote Similarity	NPD6371	Approved
0.6518	Remote Similarity	NPD5141	Approved
0.6509	Remote Similarity	NPD4202	Approved
0.6508	Remote Similarity	NPD6914	Discontinued
0.6481	Remote Similarity	NPD5222	Approved
0.6481	Remote Similarity	NPD5221	Approved
0.6481	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4697	Phase 3
0.6476	Remote Similarity	NPD6698	Approved
0.6476	Remote Similarity	NPD46	Approved
0.6475	Remote Similarity	NPD5988	Approved
0.6471	Remote Similarity	NPD6009	Approved
0.6471	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5363	Approved
0.6466	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5285	Approved
0.6455	Remote Similarity	NPD5286	Approved
0.6455	Remote Similarity	NPD4700	Approved
0.6455	Remote Similarity	NPD4696	Approved
0.6446	Remote Similarity	NPD6319	Approved
0.6436	Remote Similarity	NPD7154	Phase 3
0.6429	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5173	Approved
0.6415	Remote Similarity	NPD8034	Phase 2
0.6415	Remote Similarity	NPD8035	Phase 2
0.6415	Remote Similarity	NPD5281	Approved
0.6415	Remote Similarity	NPD5284	Approved
0.6389	Remote Similarity	NPD4629	Approved
0.6389	Remote Similarity	NPD5210	Approved
0.6389	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6274	Approved
0.6381	Remote Similarity	NPD6051	Approved
0.6381	Remote Similarity	NPD6080	Approved
0.6381	Remote Similarity	NPD6904	Approved
0.6381	Remote Similarity	NPD6673	Approved
0.6381	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD3573	Approved
0.6339	Remote Similarity	NPD5226	Approved
0.6339	Remote Similarity	NPD4633	Approved
0.6339	Remote Similarity	NPD5225	Approved
0.6339	Remote Similarity	NPD5224	Approved
0.6337	Remote Similarity	NPD4223	Phase 3
0.6337	Remote Similarity	NPD4269	Approved
0.6337	Remote Similarity	NPD5209	Approved
0.6337	Remote Similarity	NPD4270	Approved
0.6337	Remote Similarity	NPD4221	Approved
0.633	Remote Similarity	NPD7839	Suspended
0.6321	Remote Similarity	NPD5692	Phase 3
0.63	Remote Similarity	NPD4695	Discontinued
0.629	Remote Similarity	NPD6067	Discontinued
0.6289	Remote Similarity	NPD8039	Approved
0.6286	Remote Similarity	NPD5208	Approved
0.6283	Remote Similarity	NPD5175	Approved
0.6283	Remote Similarity	NPD5174	Approved
0.6275	Remote Similarity	NPD5362	Discontinued
0.6262	Remote Similarity	NPD5694	Approved
0.6262	Remote Similarity	NPD6050	Approved
0.625	Remote Similarity	NPD5223	Approved
0.625	Remote Similarity	NPD6868	Approved
0.625	Remote Similarity	NPD5786	Approved
0.6239	Remote Similarity	NPD4634	Approved
0.623	Remote Similarity	NPD7101	Approved
0.623	Remote Similarity	NPD7100	Approved
0.6224	Remote Similarity	NPD6117	Approved
0.6218	Remote Similarity	NPD4632	Approved
0.6216	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4197	Approved
0.6214	Remote Similarity	NPD3668	Phase 3
0.6198	Remote Similarity	NPD6317	Approved
0.6186	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD4767	Approved
0.6174	Remote Similarity	NPD4768	Approved
0.6174	Remote Similarity	NPD6008	Approved
0.6168	Remote Similarity	NPD5207	Approved
0.6162	Remote Similarity	NPD6116	Phase 1
0.6161	Remote Similarity	NPD6404	Discontinued
0.6154	Remote Similarity	NPD5329	Approved
0.6148	Remote Similarity	NPD6313	Approved
0.6148	Remote Similarity	NPD6314	Approved
0.6148	Remote Similarity	NPD6335	Approved
0.6147	Remote Similarity	NPD5282	Discontinued

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