NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.18
Volume:	286.539
LogP:	5.346
LogD:	4.14
LogS:	-4.329
# Rotatable Bonds:	0
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.717
Synthetic Accessibility Score:	3.517
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.697
MDCK Permeability:	1.8086071577272378e-05
Pgp-inhibitor:	0.071
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.961
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.427
Plasma Protein Binding (PPB):	96.4745864868164%
Volume Distribution (VD):	2.019
Pgp-substrate:	2.9687817096710205%

ADMET: Metabolism

CYP1A2-inhibitor:	0.877
CYP1A2-substrate:	0.823
CYP2C19-inhibitor:	0.731
CYP2C19-substrate:	0.852
CYP2C9-inhibitor:	0.461
CYP2C9-substrate:	0.863
CYP2D6-inhibitor:	0.709
CYP2D6-substrate:	0.873
CYP3A4-inhibitor:	0.83
CYP3A4-substrate:	0.645

ADMET: Excretion

Clearance (CL):	17.126
Half-life (T1/2):	0.138

ADMET: Toxicity

hERG Blockers:	0.847
Human Hepatotoxicity (H-HT):	0.213
Drug-inuced Liver Injury (DILI):	0.641
AMES Toxicity:	0.163
Rat Oral Acute Toxicity:	0.613
Maximum Recommended Daily Dose:	0.887
Skin Sensitization:	0.954
Carcinogencity:	0.682
Eye Corrosion:	0.23
Eye Irritation:	0.825
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC322753

Natural Product ID:	NPC322753
*Common Name:**	17-Deoxoestrone
IUPAC Name:	(8S,9S,13S,14S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol
Synonyms:	17-Deoxoestrone
Standard InCHIKey:	HJKVPZJVBHWFCQ-BDXSIMOUSA-N
Standard InCHI:	InChI=1S/C18H24O/c1-18-9-2-3-17(18)16-6-4-12-11-13(19)5-7-14(12)15(16)8-10-18/h5,7,11,15-17,19H,2-4,6,8-10H2,1H3/t15-,16-,17+,18+/m1/s1
SMILES:	Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL261406
PubChem CID:	5888
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001466] Estrane steroids [CHEMONTID:0003570] Estrogens and derivatives

*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
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	Wrocław, Poland	2004–2005	DOI[10.1016/J.FOODCHEM.2006.08.014]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003–2005	DOI[10.1016/j.jfca.2006.05.007]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jf950732o]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10775096]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[1622242]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16659156]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16668466]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20963508]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seeds	Tekirdag, Turkey		PMID[24499198]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25053043]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25070365]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25369450]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[25369450]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Hypocotyl	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7635	Glycine max	Species	Fabaceae	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
EC50	1
IC50	5
Kd	1
Others	5

Activity Type	# Activity
Cell Line	5
Individual Protein	5
NON-MOLECULAR	1
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	0.118	nM	PMID[458205]
NPT299	Individual Protein	Androgen Receptor	Rattus norvegicus	IC50	=	41686.94	nM	PMID[458206]
NPT83	Cell Line	MCF7	Homo sapiens	FC	=	1.91	n.a.	PMID[458208]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	8220.0	nM	PMID[458208]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	41260.0	nM	PMID[458208]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	21990.0	nM	PMID[458208]
NPT896	Individual Protein	Constitutive androstane receptor	Mus musculus	Remaining activity	=	56.0	%	PMID[458204]
NPT544	Protein Family	Estrogen receptor	Homo sapiens	Ka	=	2930000000.0	M-1	PMID[458205]
NPT895	Individual Protein	Testis-specific androgen-binding protein	Homo sapiens	Kd	=	5.012	nM	PMID[458207]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	22060.0	nM	PMID[458208]
NPT900	Individual Protein	3-keto-steroid reductase	Homo sapiens	Inhibition	=	4.5	%	PMID[458209]
NPT900	Individual Protein	3-keto-steroid reductase	Homo sapiens	Inhibition	=	6.0	%	PMID[458209]

☑ 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 NPC322753 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	347
0.1-0.2	1706
0.2-0.3	2865
0.3-0.4	9529
0.4-0.5	10994
0.5-0.6	11688
0.6-0.7	4596
0.7-0.8	815
0.8-0.85	101
0.85-0.9	36
0.9-0.95	19
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9364	High Similarity	NPC48342
0.9364	High Similarity	NPC164649
0.934	High Similarity	NPC141782
0.9333	High Similarity	NPC11554
0.9252	High Similarity	NPC260323
0.9252	High Similarity	NPC176279
0.9196	High Similarity	NPC318552
0.9196	High Similarity	NPC99734
0.9196	High Similarity	NPC190501
0.9174	High Similarity	NPC195922
0.9167	High Similarity	NPC250323
0.9159	High Similarity	NPC13482
0.9115	High Similarity	NPC328504
0.9091	High Similarity	NPC469719
0.9035	High Similarity	NPC142198
0.9035	High Similarity	NPC77569
0.9009	High Similarity	NPC257540
0.9009	High Similarity	NPC137496
0.9009	High Similarity	NPC247858
0.9009	High Similarity	NPC474358
0.9009	High Similarity	NPC474387
0.9009	High Similarity	NPC154511
0.9	High Similarity	NPC268160
0.8919	High Similarity	NPC192948
0.8919	High Similarity	NPC35797
0.8919	High Similarity	NPC147179
0.8909	High Similarity	NPC715
0.8899	High Similarity	NPC95716
0.8899	High Similarity	NPC77772
0.8879	High Similarity	NPC151477
0.8846	High Similarity	NPC211885
0.8839	High Similarity	NPC38893
0.8839	High Similarity	NPC219112
0.8839	High Similarity	NPC308828
0.8839	High Similarity	NPC477137
0.8839	High Similarity	NPC308311
0.8839	High Similarity	NPC471668
0.8818	High Similarity	NPC46940
0.8793	High Similarity	NPC321402
0.8774	High Similarity	NPC327811
0.8774	High Similarity	NPC254965
0.8772	High Similarity	NPC258366
0.8772	High Similarity	NPC473974
0.8772	High Similarity	NPC42657
0.8772	High Similarity	NPC31296
0.8772	High Similarity	NPC79933
0.8761	High Similarity	NPC16030
0.8761	High Similarity	NPC304510
0.8761	High Similarity	NPC477136
0.8761	High Similarity	NPC172219
0.8738	High Similarity	NPC202986
0.8727	High Similarity	NPC266937
0.8727	High Similarity	NPC470770
0.8716	High Similarity	NPC58865
0.8696	High Similarity	NPC68339
0.8692	High Similarity	NPC117115
0.8684	High Similarity	NPC471671
0.8684	High Similarity	NPC469609
0.8673	High Similarity	NPC469663
0.8673	High Similarity	NPC92
0.8673	High Similarity	NPC33900
0.8673	High Similarity	NPC141001
0.8661	High Similarity	NPC471534
0.8654	High Similarity	NPC225464
0.8649	High Similarity	NPC62867
0.8649	High Similarity	NPC177962
0.8644	High Similarity	NPC15127
0.8624	High Similarity	NPC64586
0.8611	High Similarity	NPC21594
0.8611	High Similarity	NPC271274
0.8609	High Similarity	NPC469644
0.8609	High Similarity	NPC93071
0.8609	High Similarity	NPC126002
0.8583	High Similarity	NPC262936
0.8583	High Similarity	NPC30491
0.8571	High Similarity	NPC92730
0.8547	High Similarity	NPC475166
0.8545	High Similarity	NPC314187
0.8544	High Similarity	NPC316301
0.8544	High Similarity	NPC27323
0.8534	High Similarity	NPC135467
0.8534	High Similarity	NPC260832
0.8532	High Similarity	NPC320439
0.8491	Intermediate Similarity	NPC225506
0.8482	Intermediate Similarity	NPC228425
0.8476	Intermediate Similarity	NPC32674
0.8475	Intermediate Similarity	NPC297057
0.8462	Intermediate Similarity	NPC222146
0.8462	Intermediate Similarity	NPC259703
0.8462	Intermediate Similarity	NPC32322
0.8462	Intermediate Similarity	NPC21216
0.8447	Intermediate Similarity	NPC55903
0.8411	Intermediate Similarity	NPC252105
0.8407	Intermediate Similarity	NPC321589
0.8407	Intermediate Similarity	NPC322239
0.8396	Intermediate Similarity	NPC122005
0.8396	Intermediate Similarity	NPC252821
0.8396	Intermediate Similarity	NPC299762
0.8396	Intermediate Similarity	NPC33675
0.8393	Intermediate Similarity	NPC151537
0.839	Intermediate Similarity	NPC253627
0.839	Intermediate Similarity	NPC162935
0.839	Intermediate Similarity	NPC249340
0.8381	Intermediate Similarity	NPC292730
0.8381	Intermediate Similarity	NPC132271
0.8381	Intermediate Similarity	NPC216520
0.8381	Intermediate Similarity	NPC82664
0.8381	Intermediate Similarity	NPC473388
0.8365	Intermediate Similarity	NPC76938
0.8362	Intermediate Similarity	NPC206
0.8362	Intermediate Similarity	NPC154030
0.835	Intermediate Similarity	NPC155908
0.835	Intermediate Similarity	NPC304541
0.8319	Intermediate Similarity	NPC471794
0.8319	Intermediate Similarity	NPC176208
0.8319	Intermediate Similarity	NPC11250
0.8305	Intermediate Similarity	NPC241001
0.8304	Intermediate Similarity	NPC296683
0.8304	Intermediate Similarity	NPC132720
0.8302	Intermediate Similarity	NPC79241
0.8302	Intermediate Similarity	NPC77492
0.8302	Intermediate Similarity	NPC6597
0.8286	Intermediate Similarity	NPC32714
0.8286	Intermediate Similarity	NPC274678
0.8286	Intermediate Similarity	NPC26244
0.8276	Intermediate Similarity	NPC299180
0.8273	Intermediate Similarity	NPC477814
0.8273	Intermediate Similarity	NPC310456
0.8269	Intermediate Similarity	NPC147284
0.8269	Intermediate Similarity	NPC210497
0.8269	Intermediate Similarity	NPC3358
0.8269	Intermediate Similarity	NPC306884
0.8269	Intermediate Similarity	NPC94139
0.8269	Intermediate Similarity	NPC162314
0.8261	Intermediate Similarity	NPC246760
0.8261	Intermediate Similarity	NPC84999
0.8257	Intermediate Similarity	NPC238696
0.8252	Intermediate Similarity	NPC192
0.825	Intermediate Similarity	NPC198014
0.825	Intermediate Similarity	NPC471187
0.8246	Intermediate Similarity	NPC317869
0.8241	Intermediate Similarity	NPC51015
0.8235	Intermediate Similarity	NPC154696
0.822	Intermediate Similarity	NPC103916
0.8214	Intermediate Similarity	NPC228343
0.8214	Intermediate Similarity	NPC254833
0.8208	Intermediate Similarity	NPC259512
0.8208	Intermediate Similarity	NPC312132
0.8197	Intermediate Similarity	NPC269598
0.8197	Intermediate Similarity	NPC9292
0.8197	Intermediate Similarity	NPC145659
0.819	Intermediate Similarity	NPC245187
0.819	Intermediate Similarity	NPC152415
0.819	Intermediate Similarity	NPC151715
0.8182	Intermediate Similarity	NPC138942
0.8182	Intermediate Similarity	NPC47284
0.8182	Intermediate Similarity	NPC181334
0.8182	Intermediate Similarity	NPC243601
0.8174	Intermediate Similarity	NPC107240
0.8167	Intermediate Similarity	NPC121168
0.8167	Intermediate Similarity	NPC120172
0.8167	Intermediate Similarity	NPC478058
0.8165	Intermediate Similarity	NPC168829
0.8158	Intermediate Similarity	NPC471179
0.8155	Intermediate Similarity	NPC177420
0.8155	Intermediate Similarity	NPC123273
0.8155	Intermediate Similarity	NPC242240
0.8155	Intermediate Similarity	NPC258219
0.8155	Intermediate Similarity	NPC98772
0.8155	Intermediate Similarity	NPC280347
0.8155	Intermediate Similarity	NPC318325
0.8148	Intermediate Similarity	NPC72729
0.8136	Intermediate Similarity	NPC323074
0.8136	Intermediate Similarity	NPC151197
0.8131	Intermediate Similarity	NPC156313
0.8125	Intermediate Similarity	NPC306295
0.8115	Intermediate Similarity	NPC87985
0.8115	Intermediate Similarity	NPC137750
0.8115	Intermediate Similarity	NPC124030
0.8113	Intermediate Similarity	NPC8392
0.8113	Intermediate Similarity	NPC144682
0.8108	Intermediate Similarity	NPC53740
0.8108	Intermediate Similarity	NPC155072
0.8095	Intermediate Similarity	NPC321502
0.8091	Intermediate Similarity	NPC323810
0.8091	Intermediate Similarity	NPC288411
0.8091	Intermediate Similarity	NPC120719
0.8077	Intermediate Similarity	NPC55561
0.8067	Intermediate Similarity	NPC318581
0.8067	Intermediate Similarity	NPC477037
0.8067	Intermediate Similarity	NPC325544
0.8058	Intermediate Similarity	NPC27974
0.8058	Intermediate Similarity	NPC25493
0.8058	Intermediate Similarity	NPC113460
0.8049	Intermediate Similarity	NPC321822
0.8049	Intermediate Similarity	NPC100414
0.8049	Intermediate Similarity	NPC325294
0.8049	Intermediate Similarity	NPC43000
0.8036	Intermediate Similarity	NPC27252
0.8036	Intermediate Similarity	NPC472979

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 NPC322753 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	942
0.2-0.3	1053
0.3-0.4	2892
0.4-0.5	2234
0.5-0.6	1316
0.6-0.7	318
0.7-0.8	61
0.8-0.85	13
0.85-0.9	3
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9364	High Similarity	NPD3091	Approved
0.9196	High Similarity	NPD3019	Approved
0.9196	High Similarity	NPD4059	Approved
0.9035	High Similarity	NPD3092	Approved
0.9027	High Similarity	NPD2932	Approved
0.886	High Similarity	NPD3095	Discontinued
0.8729	High Similarity	NPD3094	Phase 2
0.8583	High Similarity	NPD5736	Approved
0.8571	High Similarity	NPD3020	Approved
0.8544	High Similarity	NPD1432	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD3026	Approved
0.8462	Intermediate Similarity	NPD3023	Approved
0.8448	Intermediate Similarity	NPD3025	Approved
0.8448	Intermediate Similarity	NPD3024	Approved
0.8364	Intermediate Similarity	NPD2342	Discontinued
0.8347	Intermediate Similarity	NPD4624	Approved
0.8306	Intermediate Similarity	NPD6663	Approved
0.8291	Intermediate Similarity	NPD4093	Discontinued
0.8286	Intermediate Similarity	NPD2860	Approved
0.8286	Intermediate Similarity	NPD2859	Approved
0.822	Intermediate Similarity	NPD1751	Approved
0.8214	Intermediate Similarity	NPD3022	Approved
0.8214	Intermediate Similarity	NPD3021	Approved
0.8208	Intermediate Similarity	NPD288	Approved
0.819	Intermediate Similarity	NPD2934	Approved
0.819	Intermediate Similarity	NPD2933	Approved
0.8158	Intermediate Similarity	NPD7635	Approved
0.8113	Intermediate Similarity	NPD844	Approved
0.8113	Intermediate Similarity	NPD1809	Phase 2
0.8099	Intermediate Similarity	NPD5327	Phase 3
0.8095	Intermediate Similarity	NPD3620	Phase 2
0.8095	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD2605	Approved
0.8065	Intermediate Similarity	NPD2606	Approved
0.8	Intermediate Similarity	NPD5156	Approved
0.8	Intermediate Similarity	NPD5155	Approved
0.7984	Intermediate Similarity	NPD3637	Approved
0.7984	Intermediate Similarity	NPD7742	Approved
0.7984	Intermediate Similarity	NPD3635	Approved
0.7984	Intermediate Similarity	NPD3636	Approved
0.7984	Intermediate Similarity	NPD7743	Approved
0.7982	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD4140	Approved
0.7925	Intermediate Similarity	NPD845	Approved
0.792	Intermediate Similarity	NPD3594	Approved
0.792	Intermediate Similarity	NPD3595	Approved
0.7917	Intermediate Similarity	NPD2286	Discontinued
0.7903	Intermediate Similarity	NPD2195	Approved
0.7903	Intermediate Similarity	NPD2194	Approved
0.7895	Intermediate Similarity	NPD1792	Phase 2
0.7891	Intermediate Similarity	NPD5735	Approved
0.7829	Intermediate Similarity	NPD6353	Approved
0.7744	Intermediate Similarity	NPD3638	Discontinued
0.7739	Intermediate Similarity	NPD4750	Phase 3
0.7692	Intermediate Similarity	NPD4097	Suspended
0.768	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD111	Approved
0.7661	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1445	Approved
0.7632	Intermediate Similarity	NPD1444	Approved
0.763	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD2229	Approved
0.7627	Intermediate Similarity	NPD2234	Approved
0.7627	Intermediate Similarity	NPD2228	Approved
0.7597	Intermediate Similarity	NPD8032	Phase 2
0.75	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1242	Phase 1
0.748	Intermediate Similarity	NPD4589	Approved
0.7434	Intermediate Similarity	NPD940	Approved
0.7434	Intermediate Similarity	NPD846	Approved
0.7422	Intermediate Similarity	NPD2861	Phase 2
0.7368	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD1201	Approved
0.7348	Intermediate Similarity	NPD3657	Discovery
0.7339	Intermediate Similarity	NPD4626	Approved
0.7338	Intermediate Similarity	NPD3645	Discontinued
0.7333	Intermediate Similarity	NPD4725	Approved
0.7333	Intermediate Similarity	NPD4726	Approved
0.7333	Intermediate Similarity	NPD4721	Approved
0.7317	Intermediate Similarity	NPD5304	Approved
0.7317	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5303	Approved
0.7311	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1791	Approved
0.7273	Intermediate Similarity	NPD1793	Approved
0.7246	Intermediate Similarity	NPD8131	Suspended
0.7193	Intermediate Similarity	NPD3028	Approved
0.719	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5283	Phase 1
0.7188	Intermediate Similarity	NPD6696	Suspended
0.7188	Intermediate Similarity	NPD1283	Approved
0.7177	Intermediate Similarity	NPD7741	Discontinued
0.7176	Intermediate Similarity	NPD4625	Phase 3
0.7174	Intermediate Similarity	NPD8166	Discontinued
0.7163	Intermediate Similarity	NPD6273	Approved
0.7153	Intermediate Similarity	NPD7037	Approved
0.7143	Intermediate Similarity	NPD3109	Approved
0.7143	Intermediate Similarity	NPD3110	Approved
0.7143	Intermediate Similarity	NPD4060	Phase 1
0.7132	Intermediate Similarity	NPD1470	Approved
0.7131	Intermediate Similarity	NPD497	Approved
0.712	Intermediate Similarity	NPD1651	Approved
0.7113	Intermediate Similarity	NPD5699	Approved
0.7077	Intermediate Similarity	NPD6584	Phase 3
0.7077	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6671	Approved
0.7069	Intermediate Similarity	NPD9500	Approved
0.7063	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD498	Approved
0.7049	Intermediate Similarity	NPD496	Approved
0.7049	Intermediate Similarity	NPD495	Approved
0.7045	Intermediate Similarity	NPD7095	Approved
0.7037	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD2230	Approved
0.7031	Intermediate Similarity	NPD2233	Approved
0.7031	Intermediate Similarity	NPD2232	Approved
0.7025	Intermediate Similarity	NPD228	Approved
0.7009	Intermediate Similarity	NPD9608	Approved
0.7009	Intermediate Similarity	NPD9610	Approved
0.7	Intermediate Similarity	NPD5451	Approved
0.6992	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5951	Approved
0.6992	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5691	Approved
0.6984	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4749	Approved
0.6977	Remote Similarity	NPD1669	Approved
0.697	Remote Similarity	NPD4908	Phase 1
0.6953	Remote Similarity	NPD1281	Approved
0.6935	Remote Similarity	NPD7157	Approved
0.6929	Remote Similarity	NPD2667	Approved
0.6929	Remote Similarity	NPD7003	Approved
0.6929	Remote Similarity	NPD2668	Approved
0.6913	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD7833	Phase 2
0.6913	Remote Similarity	NPD7831	Phase 2
0.6912	Remote Similarity	NPD2157	Approved
0.6905	Remote Similarity	NPD7330	Discontinued
0.6889	Remote Similarity	NPD6346	Approved
0.6884	Remote Similarity	NPD5405	Approved
0.6884	Remote Similarity	NPD5408	Approved
0.6884	Remote Similarity	NPD5404	Approved
0.6884	Remote Similarity	NPD5406	Approved
0.688	Remote Similarity	NPD7340	Approved
0.6875	Remote Similarity	NPD3143	Discontinued
0.6866	Remote Similarity	NPD3764	Approved
0.6861	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.685	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6582	Phase 2
0.6846	Remote Similarity	NPD4659	Approved
0.6846	Remote Similarity	NPD6583	Phase 3
0.6846	Remote Similarity	NPD1755	Approved
0.6835	Remote Similarity	NPD5763	Approved
0.6835	Remote Similarity	NPD5762	Approved
0.6829	Remote Similarity	NPD9379	Approved
0.6829	Remote Similarity	NPD5535	Approved
0.6829	Remote Similarity	NPD9377	Approved
0.6822	Remote Similarity	NPD1610	Phase 2
0.6812	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.68	Remote Similarity	NPD709	Approved
0.6794	Remote Similarity	NPD1876	Approved
0.6786	Remote Similarity	NPD4256	Phase 2
0.6786	Remote Similarity	NPD4257	Approved
0.6783	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD2420	Approved
0.6783	Remote Similarity	NPD2421	Approved
0.6783	Remote Similarity	NPD7041	Phase 2
0.6777	Remote Similarity	NPD2684	Approved
0.6774	Remote Similarity	NPD1398	Phase 1
0.6769	Remote Similarity	NPD3070	Discontinued
0.6763	Remote Similarity	NPD6099	Approved
0.6763	Remote Similarity	NPD6100	Approved
0.6746	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4103	Phase 2
0.6742	Remote Similarity	NPD3055	Approved
0.6742	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3053	Approved
0.6735	Remote Similarity	NPD7028	Phase 2
0.672	Remote Similarity	NPD475	Phase 2
0.672	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1357	Approved
0.6713	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4818	Approved
0.6695	Remote Similarity	NPD4817	Approved
0.6693	Remote Similarity	NPD7610	Discontinued
0.6691	Remote Similarity	NPD4108	Discontinued
0.669	Remote Similarity	NPD3364	Phase 3
0.669	Remote Similarity	NPD4110	Phase 3
0.669	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3027	Phase 3
0.6667	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4198	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