NPASS Compound

Structure

NPC65513 OpenBabel07101718192D 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 -3.2709 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 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 -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 0.6994 1.9680 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 -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 2 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 2 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 1.0084 2.9190 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 10 1 0 0 0 0 2 16 1 0 0 0 0 3 16 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 6 11 2 0 0 0 0 7 12 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 12 16 1 0 0 0 0 12 17 1 1 0 0 0 13 15 1 0 0 0 0 13 17 1 1 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 20 1 6 0 0 0 15 21 1 0 0 0 0 17 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.17
Volume:	304.17
LogP:	3.513
LogD:	3.123
LogS:	-4.089
# Rotatable Bonds:	2
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.696
Synthetic Accessibility Score:	4.167
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:	-4.633
MDCK Permeability:	3.9987866330193356e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.107
Plasma Protein Binding (PPB):	79.83074951171875%
Volume Distribution (VD):	1.633
Pgp-substrate:	35.46835708618164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.303
CYP1A2-substrate:	0.133
CYP2C19-inhibitor:	0.156
CYP2C19-substrate:	0.582
CYP2C9-inhibitor:	0.216
CYP2C9-substrate:	0.1
CYP2D6-inhibitor:	0.768
CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.618
CYP3A4-substrate:	0.295

ADMET: Excretion

Clearance (CL):	5.577
Half-life (T1/2):	0.138

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.706
Drug-inuced Liver Injury (DILI):	0.178
AMES Toxicity:	0.875
Rat Oral Acute Toxicity:	0.932
Maximum Recommended Daily Dose:	0.822
Skin Sensitization:	0.929
Carcinogencity:	0.85
Eye Corrosion:	0.931
Eye Irritation:	0.623
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC65513

Natural Product ID:	NPC65513
*Common Name:**	[(1R,5As,9As,9Br)-6,6,9A-Trimethyl-3-Oxo-5,5A,7,8,9,9B-Hexahydro-1H-Benzo[G][2]Benzofuran-1-Yl] Acetate
IUPAC Name:	[(1R,5aS,9aS,9bR)-6,6,9a-trimethyl-3-oxo-5,5a,7,8,9,9b-hexahydro-1H-benzo[g][2]benzofuran-1-yl] acetate
Synonyms:
Standard InCHIKey:	SJDJUIMBNKGXTB-SHFYGJNESA-N
Standard InCHI:	InChI=1S/C17H24O4/c1-10(18)20-15-13-11(14(19)21-15)6-7-12-16(2,3)8-5-9-17(12,13)4/h6,12-13,15H,5,7-9H2,1-4H3/t12-,13+,15+,17-/m0/s1
SMILES:	CC(=O)O[C@@H]1OC(=O)C2=CC[C@@H]3[C@]([C@@H]12)(C)CCCC3(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457753
PubChem CID:	10827493
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
NPO30670	Dysidea	Genus	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374954]
NPO30670	Dysidea	Genus	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21214221]
NPO30670	Dysidea	Genus	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392880]

☑ 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	=	10.2	ug.mL-1	PMID[451591]
NPT168	Cell Line	P388	Mus musculus	IC50	=	9.0	ug.mL-1	PMID[451591]
NPT168	Cell Line	P388	Mus musculus	IC50	=	8.0	ug.mL-1	PMID[451591]
NPT168	Cell Line	P388	Mus musculus	IC50	=	10.1	ug.mL-1	PMID[451591]

☑ 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 NPC65513 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	200
0.1-0.2	1224
0.2-0.3	4944
0.3-0.4	12147
0.4-0.5	10566
0.5-0.6	6702
0.6-0.7	5719
0.7-0.8	1104
0.8-0.85	59
0.85-0.9	25
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9444	High Similarity	NPC257726
0.9444	High Similarity	NPC204054
0.9213	High Similarity	NPC166346
0.9121	High Similarity	NPC112654
0.9059	High Similarity	NPC22611
0.9043	High Similarity	NPC134077
0.8953	High Similarity	NPC71626
0.8936	High Similarity	NPC63249
0.8889	High Similarity	NPC179517
0.8889	High Similarity	NPC165904
0.8804	High Similarity	NPC473369
0.8764	High Similarity	NPC226863
0.8721	High Similarity	NPC186276
0.8706	High Similarity	NPC195424
0.8696	High Similarity	NPC477129
0.8696	High Similarity	NPC477130
0.8667	High Similarity	NPC168131
0.8636	High Similarity	NPC189311
0.8621	High Similarity	NPC472440
0.8621	High Similarity	NPC469
0.8587	High Similarity	NPC471571
0.8587	High Similarity	NPC475657
0.8571	High Similarity	NPC212679
0.8571	High Similarity	NPC220454
0.8571	High Similarity	NPC469595
0.8557	High Similarity	NPC471365
0.8557	High Similarity	NPC132395
0.8557	High Similarity	NPC471364
0.8556	High Similarity	NPC477128
0.8542	High Similarity	NPC473384
0.8511	High Similarity	NPC311166
0.8511	High Similarity	NPC319692
0.8511	High Similarity	NPC325960
0.8506	High Similarity	NPC200513
0.85	High Similarity	NPC112457
0.8478	Intermediate Similarity	NPC477783
0.8462	Intermediate Similarity	NPC251528
0.8427	Intermediate Similarity	NPC472442
0.8391	Intermediate Similarity	NPC149237
0.8384	Intermediate Similarity	NPC127790
0.837	Intermediate Similarity	NPC477782
0.8352	Intermediate Similarity	NPC215831
0.8352	Intermediate Similarity	NPC196407
0.8333	Intermediate Similarity	NPC473154
0.8333	Intermediate Similarity	NPC118266
0.8298	Intermediate Similarity	NPC88507
0.8295	Intermediate Similarity	NPC178676
0.828	Intermediate Similarity	NPC141831
0.8261	Intermediate Similarity	NPC284561
0.8261	Intermediate Similarity	NPC5509
0.8261	Intermediate Similarity	NPC73995
0.8261	Intermediate Similarity	NPC293044
0.8261	Intermediate Similarity	NPC174765
0.8247	Intermediate Similarity	NPC473219
0.8247	Intermediate Similarity	NPC470761
0.8222	Intermediate Similarity	NPC65661
0.8222	Intermediate Similarity	NPC300985
0.8222	Intermediate Similarity	NPC217394
0.8211	Intermediate Similarity	NPC183012
0.8202	Intermediate Similarity	NPC193198
0.8173	Intermediate Similarity	NPC157441
0.8172	Intermediate Similarity	NPC152467
0.8172	Intermediate Similarity	NPC159748
0.8172	Intermediate Similarity	NPC469372
0.8172	Intermediate Similarity	NPC232426
0.8172	Intermediate Similarity	NPC281942
0.8172	Intermediate Similarity	NPC101651
0.814	Intermediate Similarity	NPC316500
0.8132	Intermediate Similarity	NPC220478
0.8132	Intermediate Similarity	NPC474062
0.8132	Intermediate Similarity	NPC244174
0.8125	Intermediate Similarity	NPC73858
0.8105	Intermediate Similarity	NPC474554
0.8105	Intermediate Similarity	NPC470697
0.8085	Intermediate Similarity	NPC186363
0.8085	Intermediate Similarity	NPC233345
0.8077	Intermediate Similarity	NPC194951
0.8077	Intermediate Similarity	NPC12046
0.8068	Intermediate Similarity	NPC473685
0.8065	Intermediate Similarity	NPC174342
0.8061	Intermediate Similarity	NPC477720
0.8058	Intermediate Similarity	NPC235014
0.8041	Intermediate Similarity	NPC475709
0.8041	Intermediate Similarity	NPC472188
0.8041	Intermediate Similarity	NPC76266
0.8023	Intermediate Similarity	NPC41017
0.8022	Intermediate Similarity	NPC177932
0.8022	Intermediate Similarity	NPC473251
0.8022	Intermediate Similarity	NPC106416
0.8022	Intermediate Similarity	NPC110405
0.8022	Intermediate Similarity	NPC42586
0.8022	Intermediate Similarity	NPC86316
0.8	Intermediate Similarity	NPC267266
0.8	Intermediate Similarity	NPC469939
0.8	Intermediate Similarity	NPC277721
0.8	Intermediate Similarity	NPC254202
0.7959	Intermediate Similarity	NPC318917
0.7959	Intermediate Similarity	NPC472186
0.7959	Intermediate Similarity	NPC471366
0.7959	Intermediate Similarity	NPC23364
0.7959	Intermediate Similarity	NPC476800
0.7957	Intermediate Similarity	NPC472302
0.7938	Intermediate Similarity	NPC17578
0.7938	Intermediate Similarity	NPC470801
0.7938	Intermediate Similarity	NPC240673
0.7931	Intermediate Similarity	NPC187568
0.7931	Intermediate Similarity	NPC41780
0.7917	Intermediate Similarity	NPC475572
0.7917	Intermediate Similarity	NPC476415
0.7912	Intermediate Similarity	NPC30486
0.7912	Intermediate Similarity	NPC149869
0.7912	Intermediate Similarity	NPC159635
0.79	Intermediate Similarity	NPC31058
0.79	Intermediate Similarity	NPC469606
0.79	Intermediate Similarity	NPC273005
0.7895	Intermediate Similarity	NPC49420
0.7879	Intermediate Similarity	NPC473204
0.7879	Intermediate Similarity	NPC473545
0.7879	Intermediate Similarity	NPC472187
0.7872	Intermediate Similarity	NPC470734
0.7872	Intermediate Similarity	NPC288699
0.7857	Intermediate Similarity	NPC38530
0.7857	Intermediate Similarity	NPC474343
0.7857	Intermediate Similarity	NPC84335
0.7857	Intermediate Similarity	NPC476768
0.7849	Intermediate Similarity	NPC475678
0.7849	Intermediate Similarity	NPC312561
0.7843	Intermediate Similarity	NPC477125
0.7843	Intermediate Similarity	NPC252296
0.7841	Intermediate Similarity	NPC35574
0.7835	Intermediate Similarity	NPC295347
0.7835	Intermediate Similarity	NPC471362
0.7835	Intermediate Similarity	NPC471372
0.7835	Intermediate Similarity	NPC472189
0.7835	Intermediate Similarity	NPC33473
0.7826	Intermediate Similarity	NPC30984
0.7812	Intermediate Similarity	NPC242069
0.7812	Intermediate Similarity	NPC470576
0.7812	Intermediate Similarity	NPC115021
0.7812	Intermediate Similarity	NPC472303
0.7812	Intermediate Similarity	NPC470656
0.7802	Intermediate Similarity	NPC118423
0.78	Intermediate Similarity	NPC472643
0.7798	Intermediate Similarity	NPC474179
0.7798	Intermediate Similarity	NPC475834
0.7789	Intermediate Similarity	NPC51486
0.7778	Intermediate Similarity	NPC216478
0.7778	Intermediate Similarity	NPC252295
0.7778	Intermediate Similarity	NPC40228
0.7778	Intermediate Similarity	NPC282293
0.7778	Intermediate Similarity	NPC475665
0.7778	Intermediate Similarity	NPC176845
0.7778	Intermediate Similarity	NPC14203
0.7778	Intermediate Similarity	NPC229584
0.7778	Intermediate Similarity	NPC38642
0.7778	Intermediate Similarity	NPC23046
0.7767	Intermediate Similarity	NPC184512
0.7766	Intermediate Similarity	NPC277771
0.7755	Intermediate Similarity	NPC307164
0.7755	Intermediate Similarity	NPC171598
0.7755	Intermediate Similarity	NPC8954
0.7755	Intermediate Similarity	NPC94905
0.7753	Intermediate Similarity	NPC17550
0.7745	Intermediate Similarity	NPC146731
0.7745	Intermediate Similarity	NPC476763
0.7745	Intermediate Similarity	NPC476764
0.7742	Intermediate Similarity	NPC168248
0.7736	Intermediate Similarity	NPC222834
0.7732	Intermediate Similarity	NPC298973
0.7732	Intermediate Similarity	NPC38830
0.7732	Intermediate Similarity	NPC104925
0.7732	Intermediate Similarity	NPC476596
0.7732	Intermediate Similarity	NPC474555
0.7723	Intermediate Similarity	NPC471363
0.7723	Intermediate Similarity	NPC58329
0.7723	Intermediate Similarity	NPC238397
0.7717	Intermediate Similarity	NPC470011
0.7717	Intermediate Similarity	NPC475100
0.7717	Intermediate Similarity	NPC469569
0.7717	Intermediate Similarity	NPC100391
0.7708	Intermediate Similarity	NPC477122
0.7708	Intermediate Similarity	NPC289479
0.7708	Intermediate Similarity	NPC474631
0.7708	Intermediate Similarity	NPC303697
0.7708	Intermediate Similarity	NPC72845
0.7706	Intermediate Similarity	NPC475913
0.77	Intermediate Similarity	NPC470906
0.77	Intermediate Similarity	NPC476299
0.77	Intermediate Similarity	NPC469402
0.77	Intermediate Similarity	NPC474012
0.77	Intermediate Similarity	NPC47024
0.77	Intermediate Similarity	NPC472644
0.7692	Intermediate Similarity	NPC177524
0.7692	Intermediate Similarity	NPC471218
0.7692	Intermediate Similarity	NPC275539
0.7692	Intermediate Similarity	NPC219900
0.7692	Intermediate Similarity	NPC189075
0.7692	Intermediate Similarity	NPC268122
0.7692	Intermediate Similarity	NPC226988
0.7692	Intermediate Similarity	NPC392

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 NPC65513 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1511
0.2-0.3	3904
0.3-0.4	2384
0.4-0.5	738
0.5-0.6	249
0.6-0.7	177
0.7-0.8	21
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
0.8506	High Similarity	NPD4752	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD1694	Approved
0.7692	Intermediate Similarity	NPD6686	Approved
0.7396	Intermediate Similarity	NPD6672	Approved
0.7396	Intermediate Similarity	NPD5737	Approved
0.7368	Intermediate Similarity	NPD7521	Approved
0.7368	Intermediate Similarity	NPD5330	Approved
0.7368	Intermediate Similarity	NPD6684	Approved
0.7368	Intermediate Similarity	NPD7334	Approved
0.7368	Intermediate Similarity	NPD7146	Approved
0.7368	Intermediate Similarity	NPD6409	Approved
0.7347	Intermediate Similarity	NPD5693	Phase 1
0.7273	Intermediate Similarity	NPD6399	Phase 3
0.7255	Intermediate Similarity	NPD4225	Approved
0.7216	Intermediate Similarity	NPD6903	Approved
0.7216	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7900	Approved
0.72	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8039	Approved
0.7071	Intermediate Similarity	NPD5207	Approved
0.7009	Intermediate Similarity	NPD6008	Approved
0.699	Remote Similarity	NPD7902	Approved
0.6979	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6904	Approved
0.697	Remote Similarity	NPD6080	Approved
0.697	Remote Similarity	NPD6673	Approved
0.6961	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5695	Phase 3
0.6944	Remote Similarity	NPD6412	Phase 2
0.6939	Remote Similarity	NPD3573	Approved
0.6923	Remote Similarity	NPD5696	Approved
0.6923	Remote Similarity	NPD7638	Approved
0.69	Remote Similarity	NPD5692	Phase 3
0.6869	Remote Similarity	NPD5208	Approved
0.6863	Remote Similarity	NPD6001	Approved
0.6863	Remote Similarity	NPD7748	Approved
0.6857	Remote Similarity	NPD7640	Approved
0.6857	Remote Similarity	NPD7639	Approved
0.6842	Remote Similarity	NPD7115	Discovery
0.6832	Remote Similarity	NPD6050	Approved
0.6832	Remote Similarity	NPD5694	Approved
0.6832	Remote Similarity	NPD5281	Approved
0.6832	Remote Similarity	NPD5284	Approved
0.6827	Remote Similarity	NPD6084	Phase 2
0.6827	Remote Similarity	NPD6083	Phase 2
0.68	Remote Similarity	NPD6051	Approved
0.6789	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6882	Approved
0.6737	Remote Similarity	NPD4695	Discontinued
0.6733	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD7515	Phase 2
0.6636	Remote Similarity	NPD5697	Approved
0.6634	Remote Similarity	NPD1695	Approved
0.6633	Remote Similarity	NPD3665	Phase 1
0.6633	Remote Similarity	NPD3668	Phase 3
0.6633	Remote Similarity	NPD3666	Approved
0.6633	Remote Similarity	NPD3133	Approved
0.6607	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5209	Approved
0.6598	Remote Similarity	NPD3667	Approved
0.6577	Remote Similarity	NPD6899	Approved
0.6577	Remote Similarity	NPD6011	Approved
0.6577	Remote Similarity	NPD6881	Approved
0.6549	Remote Similarity	NPD6650	Approved
0.6549	Remote Similarity	NPD6649	Approved
0.6545	Remote Similarity	NPD5739	Approved
0.6545	Remote Similarity	NPD6675	Approved
0.6545	Remote Similarity	NPD6402	Approved
0.6545	Remote Similarity	NPD7128	Approved
0.6518	Remote Similarity	NPD6013	Approved
0.6518	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6014	Approved
0.6518	Remote Similarity	NPD6372	Approved
0.6518	Remote Similarity	NPD6012	Approved
0.6518	Remote Similarity	NPD6373	Approved
0.6514	Remote Similarity	NPD6052	Approved
0.6504	Remote Similarity	NPD7319	Approved
0.65	Remote Similarity	NPD4519	Discontinued
0.65	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4623	Approved
0.6491	Remote Similarity	NPD6053	Discontinued
0.6486	Remote Similarity	NPD5701	Approved
0.6484	Remote Similarity	NPD4691	Approved
0.6476	Remote Similarity	NPD5210	Approved
0.6476	Remote Similarity	NPD5654	Approved
0.6476	Remote Similarity	NPD4629	Approved
0.6471	Remote Similarity	NPD7503	Approved
0.6471	Remote Similarity	NPD4753	Phase 2
0.6471	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4786	Approved
0.646	Remote Similarity	NPD7290	Approved
0.646	Remote Similarity	NPD7102	Approved
0.646	Remote Similarity	NPD6883	Approved
0.6449	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4223	Phase 3
0.6429	Remote Similarity	NPD7320	Approved
0.6429	Remote Similarity	NPD4221	Approved
0.6423	Remote Similarity	NPD7736	Approved
0.6417	Remote Similarity	NPD6370	Approved
0.6415	Remote Similarity	NPD7732	Phase 3
0.641	Remote Similarity	NPD6009	Approved
0.6408	Remote Similarity	NPD46	Approved
0.6408	Remote Similarity	NPD6698	Approved
0.6404	Remote Similarity	NPD6617	Approved
0.6404	Remote Similarity	NPD8130	Phase 1
0.6404	Remote Similarity	NPD6847	Approved
0.6404	Remote Similarity	NPD6869	Approved
0.64	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6404	Discontinued
0.6374	Remote Similarity	NPD4137	Phase 3
0.6372	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8328	Phase 3
0.6356	Remote Similarity	NPD7328	Approved
0.6356	Remote Similarity	NPD7327	Approved
0.6355	Remote Similarity	NPD5959	Approved
0.6348	Remote Similarity	NPD8297	Approved
0.6346	Remote Similarity	NPD8035	Phase 2
0.6346	Remote Similarity	NPD8034	Phase 2
0.6346	Remote Similarity	NPD6411	Approved
0.6346	Remote Similarity	NPD6079	Approved
0.6341	Remote Similarity	NPD8293	Discontinued
0.6339	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6614	Approved
0.6337	Remote Similarity	NPD5690	Phase 2
0.6337	Remote Similarity	NPD5279	Phase 3
0.6333	Remote Similarity	NPD8513	Phase 3
0.6333	Remote Similarity	NPD8517	Approved
0.6333	Remote Similarity	NPD8515	Approved
0.6333	Remote Similarity	NPD8033	Approved
0.6333	Remote Similarity	NPD8516	Approved
0.6316	Remote Similarity	NPD6371	Approved
0.6311	Remote Similarity	NPD5328	Approved
0.6311	Remote Similarity	NPD7492	Approved
0.6304	Remote Similarity	NPD4747	Approved
0.6303	Remote Similarity	NPD7516	Approved
0.63	Remote Similarity	NPD4197	Approved
0.6293	Remote Similarity	NPD8133	Approved
0.6286	Remote Similarity	NPD5778	Approved
0.6286	Remote Similarity	NPD5779	Approved
0.6286	Remote Similarity	NPD4202	Approved
0.6277	Remote Similarity	NPD4058	Approved
0.6273	Remote Similarity	NPD5211	Phase 2
0.6273	Remote Similarity	NPD7632	Discontinued
0.6262	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5222	Approved
0.6262	Remote Similarity	NPD4697	Phase 3
0.6262	Remote Similarity	NPD5221	Approved
0.6261	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.626	Remote Similarity	NPD6616	Approved
0.625	Remote Similarity	NPD8294	Approved
0.625	Remote Similarity	NPD6054	Approved
0.625	Remote Similarity	NPD8377	Approved
0.6239	Remote Similarity	NPD4696	Approved
0.6239	Remote Similarity	NPD5285	Approved
0.6239	Remote Similarity	NPD5286	Approved
0.6238	Remote Similarity	NPD5329	Approved
0.6238	Remote Similarity	NPD5363	Approved
0.623	Remote Similarity	NPD6067	Discontinued
0.623	Remote Similarity	NPD7122	Discontinued
0.6226	Remote Similarity	NPD5282	Discontinued
0.621	Remote Similarity	NPD7078	Approved
0.6204	Remote Similarity	NPD4755	Approved
0.6204	Remote Similarity	NPD5173	Approved
0.6198	Remote Similarity	NPD8378	Approved
0.6198	Remote Similarity	NPD8296	Approved
0.6198	Remote Similarity	NPD8380	Approved
0.6198	Remote Similarity	NPD8335	Approved
0.6198	Remote Similarity	NPD8379	Approved
0.6198	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD6016	Approved
0.6198	Remote Similarity	NPD6015	Approved
0.6186	Remote Similarity	NPD6274	Approved
0.6186	Remote Similarity	NPD3617	Approved
0.6182	Remote Similarity	NPD5223	Approved
0.618	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5205	Approved
0.6176	Remote Similarity	NPD4690	Approved
0.6176	Remote Similarity	NPD4688	Approved
0.6176	Remote Similarity	NPD4138	Approved
0.6176	Remote Similarity	NPD4694	Approved
0.6176	Remote Similarity	NPD5280	Approved
0.6176	Remote Similarity	NPD4689	Approved
0.6176	Remote Similarity	NPD4693	Phase 3
0.6172	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5141	Approved
0.6154	Remote Similarity	NPD6101	Approved
0.6154	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4632	Approved
0.6148	Remote Similarity	NPD5988	Approved
0.6142	Remote Similarity	NPD7260	Phase 2
0.6134	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6317	Approved
0.6126	Remote Similarity	NPD5224	Approved
0.6126	Remote Similarity	NPD4633	Approved
0.6126	Remote Similarity	NPD5226	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