NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	490.22
Volume:	493.24
LogP:	1.623
LogD:	1.5
LogS:	-4.2
# Rotatable Bonds:	9
TPSA:	122.27
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.188
Synthetic Accessibility Score:	4.936
Fsp3:	0.654
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.877
MDCK Permeability:	5.5294203775702044e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.079
20% Bioavailability (F20%):	0.163
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.755
Plasma Protein Binding (PPB):	65.22456359863281%
Volume Distribution (VD):	0.697
Pgp-substrate:	50.00640106201172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.209
CYP2C19-inhibitor:	0.236
CYP2C19-substrate:	0.623
CYP2C9-inhibitor:	0.195
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.826
CYP3A4-substrate:	0.463

ADMET: Excretion

Clearance (CL):	4.597
Half-life (T1/2):	0.559

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.741
Drug-inuced Liver Injury (DILI):	0.905
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.727
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.141
Carcinogencity:	0.68
Eye Corrosion:	0.019
Eye Irritation:	0.078
Respiratory Toxicity:	0.82

Download Data

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

Natural Product: NPC476933

Natural Product ID:	NPC476933
*Common Name:**	methyl (1R,4aR,5S,8R,10aS)-5,8-diacetyloxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-2-oxo-4,5,6,7,8,9,10,10a-octahydro-3H-phenanthrene-1-carboxylate
IUPAC Name:	methyl (1R,4aR,5S,8R,10aS)-5,8-diacetyloxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-2-oxo-4,5,6,7,8,9,10,10a-octahydro-3H-phenanthrene-1-carboxylate
Synonyms:	abietane
Standard InCHIKey:	OTERBTMTWQHNQT-ZCDKHLBTSA-N
Standard InCHI:	InChI=1S/C26H34O9/c1-13(23(30)32-6)17-12-18(34-14(2)27)21-16(22(17)35-15(3)28)8-9-19-25(21,4)11-10-20(29)26(19,5)24(31)33-7/h17-19,22H,1,8-12H2,2-7H3/t17?,18-,19-,22-,25+,26+/m0/s1
SMILES:	CC(=O)O[C@H]1CC([C@H](C2=C1[C@@]3(CCC(=O)[C@]([C@H]3CC2)(C)C(=O)OC)C)OC(=O)C)C(=C)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44557093
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids [CHEMONTID:0003060] 16-oxosteroids

*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
NPO23522	Croton argyrophylloides	Species	Euphorbiaceae	Eukaryota	bark	Crato, Cear State, Brazil	2005-JAN	PMID[19780590]
NPO23522	Croton argyrophylloides	Species	Euphorbiaceae	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
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000	nM	PMID[19780590]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	>	10000	nM	PMID[19780590]
NPT399	Cell Line	SF-295	Homo sapiens	IC50	>	10000	nM	PMID[19780590]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000	nM	PMID[19780590]
NPT927	Cell Line	PBMC	Homo sapiens	IC50	>	10000	nM	PMID[19780590]

☑ 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 NPC476933 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	245
0.1-0.2	1402
0.2-0.3	4873
0.3-0.4	8390
0.4-0.5	13694
0.5-0.6	7095
0.6-0.7	5886
0.7-0.8	1091
0.8-0.85	20
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8515	High Similarity	NPC254202
0.8431	Intermediate Similarity	NPC470297
0.8431	Intermediate Similarity	NPC96268
0.8333	Intermediate Similarity	NPC159442
0.8317	Intermediate Similarity	NPC476478
0.8298	Intermediate Similarity	NPC220478
0.8265	Intermediate Similarity	NPC470697
0.819	Intermediate Similarity	NPC476479
0.819	Intermediate Similarity	NPC275539
0.819	Intermediate Similarity	NPC476802
0.819	Intermediate Similarity	NPC189075
0.819	Intermediate Similarity	NPC89171
0.8163	Intermediate Similarity	NPC475657
0.8148	Intermediate Similarity	NPC471204
0.8119	Intermediate Similarity	NPC176845
0.8113	Intermediate Similarity	NPC112457
0.8095	Intermediate Similarity	NPC112780
0.8095	Intermediate Similarity	NPC133422
0.8095	Intermediate Similarity	NPC110496
0.8061	Intermediate Similarity	NPC473944
0.8058	Intermediate Similarity	NPC80781
0.8056	Intermediate Similarity	NPC269530
0.8056	Intermediate Similarity	NPC277769
0.8041	Intermediate Similarity	NPC284561
0.8037	Intermediate Similarity	NPC253906
0.802	Intermediate Similarity	NPC38530
0.802	Intermediate Similarity	NPC84335
0.8019	Intermediate Similarity	NPC151393
0.8018	Intermediate Similarity	NPC470420
0.8	Intermediate Similarity	NPC469607
0.8	Intermediate Similarity	NPC284365
0.8	Intermediate Similarity	NPC123726
0.7982	Intermediate Similarity	NPC472926
0.7982	Intermediate Similarity	NPC470120
0.7982	Intermediate Similarity	NPC159333
0.7982	Intermediate Similarity	NPC25909
0.7981	Intermediate Similarity	NPC8196
0.7981	Intermediate Similarity	NPC95899
0.798	Intermediate Similarity	NPC271652
0.7961	Intermediate Similarity	NPC472924
0.7959	Intermediate Similarity	NPC152467
0.7946	Intermediate Similarity	NPC475520
0.7941	Intermediate Similarity	NPC264378
0.7941	Intermediate Similarity	NPC23364
0.7938	Intermediate Similarity	NPC477128
0.7938	Intermediate Similarity	NPC69713
0.7928	Intermediate Similarity	NPC134430
0.7928	Intermediate Similarity	NPC472927
0.7925	Intermediate Similarity	NPC143609
0.7905	Intermediate Similarity	NPC118911
0.7905	Intermediate Similarity	NPC146731
0.7905	Intermediate Similarity	NPC189616
0.79	Intermediate Similarity	NPC476415
0.79	Intermediate Similarity	NPC477129
0.79	Intermediate Similarity	NPC477130
0.789	Intermediate Similarity	NPC194951
0.789	Intermediate Similarity	NPC4573
0.789	Intermediate Similarity	NPC476801
0.789	Intermediate Similarity	NPC12046
0.789	Intermediate Similarity	NPC90952
0.7885	Intermediate Similarity	NPC475320
0.7885	Intermediate Similarity	NPC162973
0.7885	Intermediate Similarity	NPC136289
0.7885	Intermediate Similarity	NPC137430
0.7879	Intermediate Similarity	NPC470230
0.7864	Intermediate Similarity	NPC471413
0.7864	Intermediate Similarity	NPC54705
0.7857	Intermediate Similarity	NPC473720
0.7843	Intermediate Similarity	NPC285513
0.7843	Intermediate Similarity	NPC96839
0.7838	Intermediate Similarity	NPC176840
0.7838	Intermediate Similarity	NPC190286
0.7835	Intermediate Similarity	NPC102640
0.7835	Intermediate Similarity	NPC175293
0.783	Intermediate Similarity	NPC472389
0.783	Intermediate Similarity	NPC111952
0.7822	Intermediate Similarity	NPC471786
0.7822	Intermediate Similarity	NPC37603
0.7822	Intermediate Similarity	NPC217329
0.7818	Intermediate Similarity	NPC157441
0.7812	Intermediate Similarity	NPC110405
0.7812	Intermediate Similarity	NPC189311
0.781	Intermediate Similarity	NPC99266
0.781	Intermediate Similarity	NPC470954
0.7807	Intermediate Similarity	NPC46570
0.78	Intermediate Similarity	NPC199543
0.7798	Intermediate Similarity	NPC472928
0.7798	Intermediate Similarity	NPC324683
0.7798	Intermediate Similarity	NPC34315
0.7788	Intermediate Similarity	NPC236585
0.7788	Intermediate Similarity	NPC310981
0.7788	Intermediate Similarity	NPC473636
0.7788	Intermediate Similarity	NPC81530
0.7788	Intermediate Similarity	NPC111292
0.7788	Intermediate Similarity	NPC473514
0.7788	Intermediate Similarity	NPC77689
0.7788	Intermediate Similarity	NPC5292
0.7788	Intermediate Similarity	NPC471412
0.7788	Intermediate Similarity	NPC472637
0.7788	Intermediate Similarity	NPC472933
0.7778	Intermediate Similarity	NPC469370
0.7778	Intermediate Similarity	NPC474243
0.7778	Intermediate Similarity	NPC250018
0.7778	Intermediate Similarity	NPC475776
0.7778	Intermediate Similarity	NPC8062
0.7778	Intermediate Similarity	NPC212679
0.7778	Intermediate Similarity	NPC220454
0.7778	Intermediate Similarity	NPC113393
0.7778	Intermediate Similarity	NPC469595
0.7768	Intermediate Similarity	NPC239273
0.7768	Intermediate Similarity	NPC475809
0.7767	Intermediate Similarity	NPC471932
0.7767	Intermediate Similarity	NPC471038
0.7767	Intermediate Similarity	NPC478056
0.7767	Intermediate Similarity	NPC316598
0.7767	Intermediate Similarity	NPC216478
0.7757	Intermediate Similarity	NPC472925
0.7757	Intermediate Similarity	NPC91034
0.7757	Intermediate Similarity	NPC476958
0.7755	Intermediate Similarity	NPC24816
0.7755	Intermediate Similarity	NPC215831
0.7755	Intermediate Similarity	NPC226863
0.7748	Intermediate Similarity	NPC470953
0.7748	Intermediate Similarity	NPC474181
0.7745	Intermediate Similarity	NPC328371
0.7745	Intermediate Similarity	NPC118159
0.7745	Intermediate Similarity	NPC58052
0.7745	Intermediate Similarity	NPC42042
0.7745	Intermediate Similarity	NPC111684
0.7745	Intermediate Similarity	NPC29952
0.7739	Intermediate Similarity	NPC269642
0.7739	Intermediate Similarity	NPC107493
0.7736	Intermediate Similarity	NPC119493
0.7736	Intermediate Similarity	NPC296950
0.7732	Intermediate Similarity	NPC102996
0.7727	Intermediate Similarity	NPC265391
0.7727	Intermediate Similarity	NPC236217
0.7723	Intermediate Similarity	NPC474841
0.7723	Intermediate Similarity	NPC84893
0.7723	Intermediate Similarity	NPC250075
0.7723	Intermediate Similarity	NPC471446
0.7723	Intermediate Similarity	NPC473434
0.7723	Intermediate Similarity	NPC148463
0.7714	Intermediate Similarity	NPC469606
0.7714	Intermediate Similarity	NPC273005
0.7714	Intermediate Similarity	NPC165250
0.7714	Intermediate Similarity	NPC31058
0.7714	Intermediate Similarity	NPC40918
0.7714	Intermediate Similarity	NPC275990
0.7714	Intermediate Similarity	NPC235369
0.7706	Intermediate Similarity	NPC473627
0.7706	Intermediate Similarity	NPC5103
0.7706	Intermediate Similarity	NPC83005
0.77	Intermediate Similarity	NPC477574
0.77	Intermediate Similarity	NPC476934
0.77	Intermediate Similarity	NPC221282
0.7699	Intermediate Similarity	NPC153440
0.7699	Intermediate Similarity	NPC21326
0.7692	Intermediate Similarity	NPC475385
0.7692	Intermediate Similarity	NPC104861
0.7692	Intermediate Similarity	NPC241221
0.7692	Intermediate Similarity	NPC476299
0.7692	Intermediate Similarity	NPC473635
0.7692	Intermediate Similarity	NPC471041
0.7692	Intermediate Similarity	NPC475392
0.7692	Intermediate Similarity	NPC475202
0.7692	Intermediate Similarity	NPC174314
0.7692	Intermediate Similarity	NPC474012
0.7692	Intermediate Similarity	NPC267921
0.7692	Intermediate Similarity	NPC117685
0.7685	Intermediate Similarity	NPC470269
0.7685	Intermediate Similarity	NPC322903
0.7679	Intermediate Similarity	NPC477509
0.7679	Intermediate Similarity	NPC476963
0.7677	Intermediate Similarity	NPC280833
0.7677	Intermediate Similarity	NPC471043
0.7677	Intermediate Similarity	NPC73995
0.7672	Intermediate Similarity	NPC120724
0.7672	Intermediate Similarity	NPC469789
0.767	Intermediate Similarity	NPC474921
0.767	Intermediate Similarity	NPC474395
0.767	Intermediate Similarity	NPC226986
0.767	Intermediate Similarity	NPC254496
0.7664	Intermediate Similarity	NPC470979
0.7664	Intermediate Similarity	NPC1679
0.7664	Intermediate Similarity	NPC103088
0.7664	Intermediate Similarity	NPC470975
0.7664	Intermediate Similarity	NPC295366
0.7658	Intermediate Similarity	NPC469496
0.7658	Intermediate Similarity	NPC469454
0.7658	Intermediate Similarity	NPC469463
0.7647	Intermediate Similarity	NPC470229
0.7647	Intermediate Similarity	NPC174948
0.7647	Intermediate Similarity	NPC173875
0.7647	Intermediate Similarity	NPC274417
0.7647	Intermediate Similarity	NPC469995
0.7647	Intermediate Similarity	NPC318282
0.7647	Intermediate Similarity	NPC281134
0.7642	Intermediate Similarity	NPC159533
0.7642	Intermediate Similarity	NPC90177

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 NPC476933 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	1835
0.2-0.3	3748
0.3-0.4	2123
0.4-0.5	804
0.5-0.6	261
0.6-0.7	150
0.7-0.8	8
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
0.75	Intermediate Similarity	NPD6008	Approved
0.7449	Intermediate Similarity	NPD1694	Approved
0.7379	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7900	Approved
0.732	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5779	Approved
0.7282	Intermediate Similarity	NPD5778	Approved
0.7282	Intermediate Similarity	NPD6399	Phase 3
0.7273	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7638	Approved
0.7207	Intermediate Similarity	NPD6686	Approved
0.72	Intermediate Similarity	NPD6684	Approved
0.72	Intermediate Similarity	NPD6409	Approved
0.72	Intermediate Similarity	NPD7334	Approved
0.72	Intermediate Similarity	NPD7521	Approved
0.72	Intermediate Similarity	NPD7146	Approved
0.72	Intermediate Similarity	NPD5330	Approved
0.7196	Intermediate Similarity	NPD7639	Approved
0.7196	Intermediate Similarity	NPD7640	Approved
0.7184	Intermediate Similarity	NPD6411	Approved
0.717	Intermediate Similarity	NPD7902	Approved
0.7155	Intermediate Similarity	NPD7115	Discovery
0.7129	Intermediate Similarity	NPD3573	Approved
0.7097	Intermediate Similarity	NPD7260	Phase 2
0.708	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6672	Approved
0.7059	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6903	Approved
0.7059	Intermediate Similarity	NPD5737	Approved
0.7054	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7748	Approved
0.7018	Intermediate Similarity	NPD6650	Approved
0.7018	Intermediate Similarity	NPD6649	Approved
0.6991	Remote Similarity	NPD6372	Approved
0.6991	Remote Similarity	NPD6373	Approved
0.699	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6101	Approved
0.6981	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6319	Approved
0.6957	Remote Similarity	NPD6053	Discontinued
0.6944	Remote Similarity	NPD4225	Approved
0.6942	Remote Similarity	NPD8328	Phase 3
0.6905	Remote Similarity	NPD6845	Suspended
0.6903	Remote Similarity	NPD6881	Approved
0.6903	Remote Similarity	NPD6899	Approved
0.6875	Remote Similarity	NPD7128	Approved
0.6875	Remote Similarity	NPD6402	Approved
0.6875	Remote Similarity	NPD5739	Approved
0.6875	Remote Similarity	NPD6675	Approved
0.6864	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5693	Phase 1
0.6857	Remote Similarity	NPD7515	Phase 2
0.6842	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5697	Approved
0.681	Remote Similarity	NPD8297	Approved
0.681	Remote Similarity	NPD6882	Approved
0.68	Remote Similarity	NPD7319	Approved
0.6783	Remote Similarity	NPD7102	Approved
0.6783	Remote Similarity	NPD7290	Approved
0.6783	Remote Similarity	NPD6883	Approved
0.6783	Remote Similarity	NPD6371	Approved
0.6762	Remote Similarity	NPD5785	Approved
0.6762	Remote Similarity	NPD46	Approved
0.6762	Remote Similarity	NPD6698	Approved
0.6757	Remote Similarity	NPD7632	Discontinued
0.6754	Remote Similarity	NPD7320	Approved
0.6754	Remote Similarity	NPD6011	Approved
0.6752	Remote Similarity	NPD4632	Approved
0.6748	Remote Similarity	NPD7492	Approved
0.6724	Remote Similarity	NPD6847	Approved
0.6724	Remote Similarity	NPD8130	Phase 1
0.6724	Remote Similarity	NPD6869	Approved
0.6724	Remote Similarity	NPD6617	Approved
0.6698	Remote Similarity	NPD6050	Approved
0.6698	Remote Similarity	NPD6079	Approved
0.6698	Remote Similarity	NPD7983	Approved
0.6696	Remote Similarity	NPD6014	Approved
0.6696	Remote Similarity	NPD6013	Approved
0.6696	Remote Similarity	NPD6012	Approved
0.6694	Remote Similarity	NPD6616	Approved
0.6694	Remote Similarity	NPD7507	Approved
0.6694	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6051	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.664	Remote Similarity	NPD7078	Approved
0.6639	Remote Similarity	NPD8513	Phase 3
0.6639	Remote Similarity	NPD8516	Approved
0.6639	Remote Similarity	NPD8517	Approved
0.6639	Remote Similarity	NPD8515	Approved
0.6606	Remote Similarity	NPD7732	Phase 3
0.6604	Remote Similarity	NPD5692	Phase 3
0.6604	Remote Similarity	NPD5207	Approved
0.6602	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD8039	Approved
0.6587	Remote Similarity	NPD7736	Approved
0.6585	Remote Similarity	NPD6370	Approved
0.6583	Remote Similarity	NPD6009	Approved
0.6581	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6059	Approved
0.6545	Remote Similarity	NPD6084	Phase 2
0.6545	Remote Similarity	NPD6083	Phase 2
0.6542	Remote Similarity	NPD8035	Phase 2
0.6542	Remote Similarity	NPD5694	Approved
0.6542	Remote Similarity	NPD5284	Approved
0.6542	Remote Similarity	NPD8034	Phase 2
0.6542	Remote Similarity	NPD5281	Approved
0.6538	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3618	Phase 1
0.6538	Remote Similarity	NPD6098	Approved
0.6532	Remote Similarity	NPD7604	Phase 2
0.6522	Remote Similarity	NPD6412	Phase 2
0.6509	Remote Similarity	NPD1695	Approved
0.6509	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD8293	Discontinued
0.6505	Remote Similarity	NPD3668	Phase 3
0.6505	Remote Similarity	NPD4786	Approved
0.6504	Remote Similarity	NPD6015	Approved
0.6504	Remote Similarity	NPD5983	Phase 2
0.6504	Remote Similarity	NPD6921	Approved
0.6504	Remote Similarity	NPD6016	Approved
0.6496	Remote Similarity	NPD4634	Approved
0.6486	Remote Similarity	NPD5696	Approved
0.6471	Remote Similarity	NPD3667	Approved
0.6471	Remote Similarity	NPD5209	Approved
0.646	Remote Similarity	NPD5211	Phase 2
0.6455	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4697	Phase 3
0.6455	Remote Similarity	NPD5221	Approved
0.6455	Remote Similarity	NPD5222	Approved
0.6452	Remote Similarity	NPD5988	Approved
0.6436	Remote Similarity	NPD4695	Discontinued
0.6429	Remote Similarity	NPD5285	Approved
0.6429	Remote Similarity	NPD5286	Approved
0.6429	Remote Similarity	NPD6336	Discontinued
0.6429	Remote Similarity	NPD4696	Approved
0.6422	Remote Similarity	NPD5282	Discontinued
0.6422	Remote Similarity	NPD6001	Approved
0.6415	Remote Similarity	NPD5208	Approved
0.6396	Remote Similarity	NPD4755	Approved
0.6396	Remote Similarity	NPD5173	Approved
0.6393	Remote Similarity	NPD6335	Approved
0.6389	Remote Similarity	NPD7637	Suspended
0.6381	Remote Similarity	NPD5786	Approved
0.6378	Remote Similarity	NPD8074	Phase 3
0.6372	Remote Similarity	NPD5223	Approved
0.6364	Remote Similarity	NPD6274	Approved
0.6364	Remote Similarity	NPD6868	Approved
0.6348	Remote Similarity	NPD5141	Approved
0.6346	Remote Similarity	NPD3133	Approved
0.6346	Remote Similarity	NPD3666	Approved
0.6346	Remote Similarity	NPD3665	Phase 1
0.6341	Remote Similarity	NPD7100	Approved
0.6341	Remote Similarity	NPD7101	Approved
0.6339	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5226	Approved
0.6316	Remote Similarity	NPD5225	Approved
0.6316	Remote Similarity	NPD5224	Approved
0.6316	Remote Similarity	NPD4633	Approved
0.6311	Remote Similarity	NPD6317	Approved
0.6306	Remote Similarity	NPD7839	Suspended
0.6306	Remote Similarity	NPD7614	Phase 1
0.6296	Remote Similarity	NPD7838	Discovery
0.6286	Remote Similarity	NPD5363	Approved
0.6283	Remote Similarity	NPD4700	Approved
0.6283	Remote Similarity	NPD6648	Approved
0.6261	Remote Similarity	NPD5175	Approved
0.6261	Remote Similarity	NPD5174	Approved
0.626	Remote Similarity	NPD6313	Approved
0.626	Remote Similarity	NPD6314	Approved
0.624	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.624	Remote Similarity	NPD7503	Approved
0.6228	Remote Similarity	NPD5344	Discontinued
0.6226	Remote Similarity	NPD5279	Phase 3
0.6216	Remote Similarity	NPD5654	Approved
0.6202	Remote Similarity	NPD6033	Approved
0.6198	Remote Similarity	NPD8133	Approved
0.6186	Remote Similarity	NPD4730	Approved
0.6186	Remote Similarity	NPD4729	Approved
0.6182	Remote Similarity	NPD4202	Approved
0.6167	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4270	Approved
0.6154	Remote Similarity	NPD4768	Approved
0.6154	Remote Similarity	NPD4767	Approved
0.6154	Remote Similarity	NPD4269	Approved
0.6132	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7327	Approved
0.6129	Remote Similarity	NPD7328	Approved
0.6121	Remote Similarity	NPD6052	Approved
0.6121	Remote Similarity	NPD4754	Approved
0.6111	Remote Similarity	NPD8033	Approved
0.6111	Remote Similarity	NPD6909	Approved
0.6111	Remote Similarity	NPD6908	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