NPASS Compound

Structure

NPC151488 OpenBabel07101719152D 31 35 0 0 1 0 0 0 0 0999 V2000 -4.6046 -5.7641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9574 -6.2993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9866 -3.8620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3830 -3.9814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6146 -2.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3393 -4.3972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0303 -3.4461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5380 -0.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -1.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 1.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 0.5219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3309 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6265 -5.5562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3175 -4.6051 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0522 -3.2382 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5380 0.5219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -0.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7431 -2.2872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0739 -0.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 0.5219 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9400 1.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8060 -0.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2079 -1.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2079 -0.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4041 1.0219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 2.0219 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 16 1 0 0 0 0 2 16 1 0 0 0 0 6 27 1 0 0 0 0 7 8 2 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 13 19 1 0 0 0 0 13 23 1 0 0 0 0 14 22 2 0 0 0 0 14 24 1 0 0 0 0 15 21 1 0 0 0 0 15 25 1 0 0 0 0 16 17 1 0 0 0 0 17 3 1 1 0 0 0 18 4 1 6 0 0 0 18 21 1 0 0 0 0 19 29 2 0 0 0 0 20 22 1 0 0 0 0 20 26 1 1 0 0 0 21 27 1 1 0 0 0 23 24 1 0 0 0 0 23 26 1 6 0 0 0 24 30 2 0 0 0 0 25 28 1 6 0 0 0 25 31 1 0 0 0 0 26 5 1 1 0 0 0 27 28 1 1 0 0 0 28 22 1 6 0 0 0 28 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.3
Volume:	465.887
LogP:	4.647
LogD:	4.723
LogS:	-4.89
# Rotatable Bonds:	4
TPSA:	46.67
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.406
Synthetic Accessibility Score:	5.701
Fsp3:	0.786
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:	-4.935
MDCK Permeability:	3.472031312412582e-05
Pgp-inhibitor:	0.921
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.429
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.192
Plasma Protein Binding (PPB):	79.47130584716797%
Volume Distribution (VD):	1.251
Pgp-substrate:	2.317084312438965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.682
CYP2C19-inhibitor:	0.086
CYP2C19-substrate:	0.953
CYP2C9-inhibitor:	0.431
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.105
CYP3A4-inhibitor:	0.849
CYP3A4-substrate:	0.929

ADMET: Excretion

Clearance (CL):	7.508
Half-life (T1/2):	0.527

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.431
Drug-inuced Liver Injury (DILI):	0.299
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.973
Maximum Recommended Daily Dose:	0.574
Skin Sensitization:	0.4
Carcinogencity:	0.032
Eye Corrosion:	0.021
Eye Irritation:	0.056
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC151488

Natural Product ID:	NPC151488
*Common Name:**	Gymnasterone B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NMGBSMCZPMYTKL-DBRZCXIFSA-N
Standard InCHI:	InChI=1S/C28H40O3/c1-16(2)17(3)7-8-18(4)21-15-25-28(31-25)22-14-24(30)23-13-19(29)9-11-26(23,5)20(22)10-12-27(21,28)6/h7-8,14,16-18,20-21,23,25H,9-13,15H2,1-6H3/b8-7+/t17-,18+,20-,21+,23-,25+,26+,27+,28+/m0/s1
SMILES:	O=C1CC[C@]2([C@@H](C1)C(=O)C=C1[C@@H]2CC[C@]2([C@]31O[C@@H]3C[C@@H]2[C@@H](/C=C/[C@@H](C(C)C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251666
PubChem CID:	24179237
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids

*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
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067147]
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17988094]
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18284207]
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25600409]

☑ 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
ED50	1
GI50	39

Activity Type	# Activity
Cell Line	35
NON-MOLECULAR	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.6	ug ml-1	PMID[537680]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	33884.42	nM	PMID[537680]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	33113.11	nM	PMID[537680]
NPT380	Cell Line	U-251	Homo sapiens	GI50	<	100000.0	nM	PMID[537680]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	<	100000.0	nM	PMID[537680]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	=	36307.81	nM	PMID[537680]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	<	100000.0	nM	PMID[537680]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	=	56234.13	nM	PMID[537680]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	<	100000.0	nM	PMID[537680]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	=	51286.14	nM	PMID[537680]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	30199.52	nM	PMID[537680]
NPT386	Cell Line	KM12	Homo sapiens	GI50	=	67608.3	nM	PMID[537680]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	=	69183.1	nM	PMID[537680]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	=	95499.26	nM	PMID[537680]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	=	70794.58	nM	PMID[537680]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	=	41686.94	nM	PMID[537680]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	=	26915.35	nM	PMID[537680]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	<	100000.0	nM	PMID[537680]
NPT81	Cell Line	A549	Homo sapiens	GI50	<	100000.0	nM	PMID[537680]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	=	41686.94	nM	PMID[537680]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	=	12882.5	nM	PMID[537680]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	=	87096.36	nM	PMID[537680]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	=	66069.34	nM	PMID[537680]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	=	48977.88	nM	PMID[537680]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	=	67608.3	nM	PMID[537680]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	<	100000.0	nM	PMID[537680]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	<	100000.0	nM	PMID[537680]
NPT2722	Cell Line	St-4	Homo sapiens	GI50	<	100000.0	nM	PMID[537680]
NPT2398	Cell Line	MKN-7	Homo sapiens	GI50	=	47863.01	nM	PMID[537680]
NPT1179	Cell Line	MKN-28	Homo sapiens	GI50	=	60255.96	nM	PMID[537680]
NPT1097	Cell Line	MKN-45	Homo sapiens	GI50	=	72443.6	nM	PMID[537680]
NPT2723	Cell Line	MKN-74	Homo sapiens	GI50	=	83176.38	nM	PMID[537680]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	28840.32	nM	PMID[537680]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	=	44668.36	nM	PMID[537680]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	89125.09	nM	PMID[537680]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	<	100000.0	nM	PMID[537680]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	15135.61	nM	PMID[537680]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	26915.35	nM	PMID[537680]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	45708.82	nM	PMID[537680]

☑ 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 NPC151488 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	254
0.1-0.2	1397
0.2-0.3	5030
0.3-0.4	13352
0.4-0.5	9098
0.5-0.6	7206
0.6-0.7	5030
0.7-0.8	1284
0.8-0.85	41
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8556	High Similarity	NPC470046
0.8556	High Similarity	NPC470047
0.8515	High Similarity	NPC60681
0.8478	Intermediate Similarity	NPC470050
0.8478	Intermediate Similarity	NPC470051
0.8469	Intermediate Similarity	NPC176845
0.8421	Intermediate Similarity	NPC190442
0.8351	Intermediate Similarity	NPC33473
0.8333	Intermediate Similarity	NPC229976
0.828	Intermediate Similarity	NPC195640
0.8247	Intermediate Similarity	NPC38830
0.8235	Intermediate Similarity	NPC189616
0.8229	Intermediate Similarity	NPC49420
0.8229	Intermediate Similarity	NPC475806
0.8218	Intermediate Similarity	NPC185530
0.8211	Intermediate Similarity	NPC2983
0.8211	Intermediate Similarity	NPC177141
0.8182	Intermediate Similarity	NPC110937
0.8173	Intermediate Similarity	NPC177064
0.8172	Intermediate Similarity	NPC323765
0.8172	Intermediate Similarity	NPC470048
0.8172	Intermediate Similarity	NPC137493
0.8172	Intermediate Similarity	NPC476678
0.8137	Intermediate Similarity	NPC26478
0.8131	Intermediate Similarity	NPC122056
0.8125	Intermediate Similarity	NPC273199
0.8125	Intermediate Similarity	NPC48010
0.8125	Intermediate Similarity	NPC320026
0.8119	Intermediate Similarity	NPC310981
0.8113	Intermediate Similarity	NPC470960
0.81	Intermediate Similarity	NPC252295
0.81	Intermediate Similarity	NPC98868
0.8091	Intermediate Similarity	NPC264954
0.8081	Intermediate Similarity	NPC322063
0.8081	Intermediate Similarity	NPC160056
0.8077	Intermediate Similarity	NPC475294
0.8077	Intermediate Similarity	NPC471601
0.8061	Intermediate Similarity	NPC8993
0.8037	Intermediate Similarity	NPC475524
0.8037	Intermediate Similarity	NPC100267
0.8021	Intermediate Similarity	NPC473999
0.8021	Intermediate Similarity	NPC309603
0.802	Intermediate Similarity	NPC112167
0.802	Intermediate Similarity	NPC154072
0.8019	Intermediate Similarity	NPC76084
0.8018	Intermediate Similarity	NPC474370
0.8	Intermediate Similarity	NPC58063
0.8	Intermediate Similarity	NPC291634
0.8	Intermediate Similarity	NPC470052
0.8	Intermediate Similarity	NPC84335
0.8	Intermediate Similarity	NPC475740
0.8	Intermediate Similarity	NPC38530
0.8	Intermediate Similarity	NPC126815
0.7981	Intermediate Similarity	NPC257353
0.798	Intermediate Similarity	NPC259286
0.798	Intermediate Similarity	NPC271195
0.7961	Intermediate Similarity	NPC311612
0.7959	Intermediate Similarity	NPC474736
0.7946	Intermediate Similarity	NPC473256
0.7946	Intermediate Similarity	NPC470878
0.7941	Intermediate Similarity	NPC476897
0.7941	Intermediate Similarity	NPC168319
0.7941	Intermediate Similarity	NPC194028
0.7938	Intermediate Similarity	NPC8062
0.7917	Intermediate Similarity	NPC28227
0.7917	Intermediate Similarity	NPC471722
0.7917	Intermediate Similarity	NPC215831
0.7912	Intermediate Similarity	NPC476177
0.7909	Intermediate Similarity	NPC243065
0.7909	Intermediate Similarity	NPC470492
0.7909	Intermediate Similarity	NPC140055
0.7909	Intermediate Similarity	NPC167606
0.7909	Intermediate Similarity	NPC286528
0.7909	Intermediate Similarity	NPC20302
0.7905	Intermediate Similarity	NPC144459
0.79	Intermediate Similarity	NPC78473
0.79	Intermediate Similarity	NPC249954
0.79	Intermediate Similarity	NPC307164
0.7895	Intermediate Similarity	NPC31564
0.7895	Intermediate Similarity	NPC474733
0.7895	Intermediate Similarity	NPC264127
0.7895	Intermediate Similarity	NPC469994
0.7895	Intermediate Similarity	NPC286153
0.7895	Intermediate Similarity	NPC145879
0.7895	Intermediate Similarity	NPC474778
0.7895	Intermediate Similarity	NPC474732
0.7879	Intermediate Similarity	NPC294266
0.7879	Intermediate Similarity	NPC111015
0.7876	Intermediate Similarity	NPC88326
0.7876	Intermediate Similarity	NPC153700
0.7872	Intermediate Similarity	NPC82902
0.7872	Intermediate Similarity	NPC58841
0.7872	Intermediate Similarity	NPC161423
0.7872	Intermediate Similarity	NPC329043
0.7872	Intermediate Similarity	NPC227064
0.7872	Intermediate Similarity	NPC214043
0.7872	Intermediate Similarity	NPC321187
0.7872	Intermediate Similarity	NPC85774
0.7864	Intermediate Similarity	NPC308351
0.7864	Intermediate Similarity	NPC271266
0.7864	Intermediate Similarity	NPC22388
0.7864	Intermediate Similarity	NPC477915
0.7864	Intermediate Similarity	NPC155332
0.7864	Intermediate Similarity	NPC32577
0.7864	Intermediate Similarity	NPC114540
0.7864	Intermediate Similarity	NPC473424
0.7864	Intermediate Similarity	NPC87351
0.7857	Intermediate Similarity	NPC472975
0.7857	Intermediate Similarity	NPC262870
0.7857	Intermediate Similarity	NPC272746
0.7857	Intermediate Similarity	NPC473998
0.7857	Intermediate Similarity	NPC218301
0.785	Intermediate Similarity	NPC16270
0.7849	Intermediate Similarity	NPC193347
0.7843	Intermediate Similarity	NPC470906
0.7843	Intermediate Similarity	NPC201406
0.7838	Intermediate Similarity	NPC50774
0.7838	Intermediate Similarity	NPC470420
0.7838	Intermediate Similarity	NPC709
0.7838	Intermediate Similarity	NPC257457
0.7838	Intermediate Similarity	NPC311554
0.7835	Intermediate Similarity	NPC73995
0.7835	Intermediate Similarity	NPC285982
0.7835	Intermediate Similarity	NPC477943
0.7835	Intermediate Similarity	NPC31985
0.7835	Intermediate Similarity	NPC305039
0.7835	Intermediate Similarity	NPC76879
0.7835	Intermediate Similarity	NPC469323
0.7835	Intermediate Similarity	NPC1015
0.783	Intermediate Similarity	NPC472825
0.7822	Intermediate Similarity	NPC57416
0.7822	Intermediate Similarity	NPC2049
0.7822	Intermediate Similarity	NPC253826
0.7822	Intermediate Similarity	NPC23680
0.7822	Intermediate Similarity	NPC107243
0.7818	Intermediate Similarity	NPC148458
0.7818	Intermediate Similarity	NPC190286
0.7812	Intermediate Similarity	NPC317590
0.781	Intermediate Similarity	NPC470267
0.781	Intermediate Similarity	NPC149047
0.7807	Intermediate Similarity	NPC204812
0.78	Intermediate Similarity	NPC472932
0.78	Intermediate Similarity	NPC281134
0.78	Intermediate Similarity	NPC84383
0.7798	Intermediate Similarity	NPC317210
0.7789	Intermediate Similarity	NPC474218
0.7789	Intermediate Similarity	NPC470574
0.7789	Intermediate Similarity	NPC471224
0.7789	Intermediate Similarity	NPC469948
0.7788	Intermediate Similarity	NPC112009
0.7788	Intermediate Similarity	NPC473283
0.7788	Intermediate Similarity	NPC247957
0.7788	Intermediate Similarity	NPC236390
0.7788	Intermediate Similarity	NPC475526
0.7788	Intermediate Similarity	NPC36321
0.7788	Intermediate Similarity	NPC180204
0.7788	Intermediate Similarity	NPC249187
0.7788	Intermediate Similarity	NPC329345
0.7788	Intermediate Similarity	NPC36688
0.7778	Intermediate Similarity	NPC79117
0.7778	Intermediate Similarity	NPC69454
0.7778	Intermediate Similarity	NPC12722
0.7768	Intermediate Similarity	NPC473274
0.7768	Intermediate Similarity	NPC473270
0.7768	Intermediate Similarity	NPC470495
0.7768	Intermediate Similarity	NPC475520
0.7767	Intermediate Similarity	NPC99411
0.7766	Intermediate Similarity	NPC193198
0.7757	Intermediate Similarity	NPC214644
0.7755	Intermediate Similarity	NPC161638
0.7755	Intermediate Similarity	NPC69622
0.7755	Intermediate Similarity	NPC478258
0.7755	Intermediate Similarity	NPC474842
0.7755	Intermediate Similarity	NPC475965
0.7755	Intermediate Similarity	NPC478257
0.7748	Intermediate Similarity	NPC470493
0.7748	Intermediate Similarity	NPC312824
0.7748	Intermediate Similarity	NPC239273
0.7748	Intermediate Similarity	NPC183580
0.7745	Intermediate Similarity	NPC57079
0.7745	Intermediate Similarity	NPC103051
0.7745	Intermediate Similarity	NPC108368
0.7739	Intermediate Similarity	NPC32868
0.7739	Intermediate Similarity	NPC8374
0.7739	Intermediate Similarity	NPC241456
0.7736	Intermediate Similarity	NPC475060
0.7736	Intermediate Similarity	NPC220229
0.7736	Intermediate Similarity	NPC185
0.7732	Intermediate Similarity	NPC328539
0.7732	Intermediate Similarity	NPC97884
0.7732	Intermediate Similarity	NPC477128
0.7732	Intermediate Similarity	NPC472220
0.7732	Intermediate Similarity	NPC328313
0.7727	Intermediate Similarity	NPC238667
0.7727	Intermediate Similarity	NPC67259
0.7727	Intermediate Similarity	NPC147912
0.7714	Intermediate Similarity	NPC472868
0.7714	Intermediate Similarity	NPC119493
0.7714	Intermediate Similarity	NPC204833
0.7714	Intermediate Similarity	NPC209502

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 NPC151488 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	1527
0.2-0.3	4023
0.3-0.4	2324
0.4-0.5	621
0.5-0.6	169
0.6-0.7	139
0.7-0.8	128
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.828	Intermediate Similarity	NPD5330	Approved
0.828	Intermediate Similarity	NPD7334	Approved
0.828	Intermediate Similarity	NPD6409	Approved
0.828	Intermediate Similarity	NPD7146	Approved
0.828	Intermediate Similarity	NPD6684	Approved
0.828	Intermediate Similarity	NPD7521	Approved
0.8163	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD6903	Approved
0.8105	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD5693	Phase 1
0.7981	Intermediate Similarity	NPD6008	Approved
0.7959	Intermediate Similarity	NPD4202	Approved
0.7909	Intermediate Similarity	NPD7115	Discovery
0.7879	Intermediate Similarity	NPD6001	Approved
0.7872	Intermediate Similarity	NPD3666	Approved
0.7872	Intermediate Similarity	NPD3133	Approved
0.7872	Intermediate Similarity	NPD3665	Phase 1
0.7857	Intermediate Similarity	NPD6079	Approved
0.7849	Intermediate Similarity	NPD4223	Phase 3
0.7849	Intermediate Similarity	NPD4221	Approved
0.7835	Intermediate Similarity	NPD6673	Approved
0.7835	Intermediate Similarity	NPD5328	Approved
0.7835	Intermediate Similarity	NPD6080	Approved
0.7835	Intermediate Similarity	NPD6904	Approved
0.7789	Intermediate Similarity	NPD5329	Approved
0.7732	Intermediate Similarity	NPD5208	Approved
0.7732	Intermediate Similarity	NPD6672	Approved
0.7732	Intermediate Similarity	NPD5737	Approved
0.7708	Intermediate Similarity	NPD3618	Phase 1
0.7708	Intermediate Similarity	NPD6098	Approved
0.7692	Intermediate Similarity	NPD5211	Phase 2
0.7684	Intermediate Similarity	NPD4786	Approved
0.7684	Intermediate Similarity	NPD4197	Approved
0.767	Intermediate Similarity	NPD4696	Approved
0.767	Intermediate Similarity	NPD5285	Approved
0.767	Intermediate Similarity	NPD5286	Approved
0.7664	Intermediate Similarity	NPD6881	Approved
0.7664	Intermediate Similarity	NPD6899	Approved
0.7653	Intermediate Similarity	NPD6051	Approved
0.7653	Intermediate Similarity	NPD4753	Phase 2
0.7647	Intermediate Similarity	NPD6083	Phase 2
0.7647	Intermediate Similarity	NPD4755	Approved
0.7647	Intermediate Similarity	NPD6084	Phase 2
0.7642	Intermediate Similarity	NPD6675	Approved
0.7642	Intermediate Similarity	NPD5739	Approved
0.7642	Intermediate Similarity	NPD7128	Approved
0.7642	Intermediate Similarity	NPD6402	Approved
0.7615	Intermediate Similarity	NPD6649	Approved
0.7615	Intermediate Similarity	NPD6650	Approved
0.7604	Intermediate Similarity	NPD1694	Approved
0.76	Intermediate Similarity	NPD6399	Phase 3
0.7596	Intermediate Similarity	NPD5223	Approved
0.7593	Intermediate Similarity	NPD6372	Approved
0.7593	Intermediate Similarity	NPD6373	Approved
0.7576	Intermediate Similarity	NPD5207	Approved
0.7573	Intermediate Similarity	NPD7638	Approved
0.757	Intermediate Similarity	NPD5697	Approved
0.7547	Intermediate Similarity	NPD5141	Approved
0.7526	Intermediate Similarity	NPD5690	Phase 2
0.7526	Intermediate Similarity	NPD5205	Approved
0.7526	Intermediate Similarity	NPD4689	Approved
0.7526	Intermediate Similarity	NPD4138	Approved
0.7526	Intermediate Similarity	NPD4690	Approved
0.7526	Intermediate Similarity	NPD4688	Approved
0.7526	Intermediate Similarity	NPD4693	Phase 3
0.7524	Intermediate Similarity	NPD5224	Approved
0.7524	Intermediate Similarity	NPD5225	Approved
0.7524	Intermediate Similarity	NPD5226	Approved
0.7524	Intermediate Similarity	NPD4633	Approved
0.7523	Intermediate Similarity	NPD7102	Approved
0.7523	Intermediate Similarity	NPD7290	Approved
0.7523	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD6011	Approved
0.75	Intermediate Similarity	NPD4700	Approved
0.75	Intermediate Similarity	NPD6050	Approved
0.75	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.75	Intermediate Similarity	NPD5694	Approved
0.75	Intermediate Similarity	NPD7640	Approved
0.7474	Intermediate Similarity	NPD3667	Approved
0.7455	Intermediate Similarity	NPD8130	Phase 1
0.7455	Intermediate Similarity	NPD6617	Approved
0.7455	Intermediate Similarity	NPD6869	Approved
0.7455	Intermediate Similarity	NPD6847	Approved
0.7453	Intermediate Similarity	NPD5175	Approved
0.7453	Intermediate Similarity	NPD5174	Approved
0.7451	Intermediate Similarity	NPD4629	Approved
0.7451	Intermediate Similarity	NPD5210	Approved
0.7451	Intermediate Similarity	NPD5695	Phase 3
0.7431	Intermediate Similarity	NPD6013	Approved
0.7431	Intermediate Similarity	NPD6012	Approved
0.7431	Intermediate Similarity	NPD6014	Approved
0.7407	Intermediate Similarity	NPD5701	Approved
0.7404	Intermediate Similarity	NPD5696	Approved
0.74	Intermediate Similarity	NPD5692	Phase 3
0.7387	Intermediate Similarity	NPD6882	Approved
0.7387	Intermediate Similarity	NPD8297	Approved
0.7379	Intermediate Similarity	NPD5221	Approved
0.7379	Intermediate Similarity	NPD5222	Approved
0.7379	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4697	Phase 3
0.7353	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7900	Approved
0.7347	Intermediate Similarity	NPD4694	Approved
0.7347	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5280	Approved
0.734	Intermediate Similarity	NPD4195	Approved
0.732	Intermediate Similarity	NPD3668	Phase 3
0.7308	Intermediate Similarity	NPD5173	Approved
0.7297	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4754	Approved
0.7273	Intermediate Similarity	NPD3573	Approved
0.7222	Intermediate Similarity	NPD4747	Approved
0.7216	Intermediate Similarity	NPD4788	Approved
0.7184	Intermediate Similarity	NPD7748	Approved
0.7182	Intermediate Similarity	NPD4729	Approved
0.7182	Intermediate Similarity	NPD4730	Approved
0.7172	Intermediate Similarity	NPD5279	Phase 3
0.7172	Intermediate Similarity	NPD4623	Approved
0.7172	Intermediate Similarity	NPD4519	Discontinued
0.7157	Intermediate Similarity	NPD5281	Approved
0.7157	Intermediate Similarity	NPD5284	Approved
0.7156	Intermediate Similarity	NPD4768	Approved
0.7156	Intermediate Similarity	NPD4767	Approved
0.7143	Intermediate Similarity	NPD7902	Approved
0.7111	Intermediate Similarity	NPD4137	Phase 3
0.7091	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6335	Approved
0.7054	Intermediate Similarity	NPD5249	Phase 3
0.7054	Intermediate Similarity	NPD5248	Approved
0.7054	Intermediate Similarity	NPD5250	Approved
0.7054	Intermediate Similarity	NPD5169	Approved
0.7054	Intermediate Similarity	NPD5251	Approved
0.7054	Intermediate Similarity	NPD5247	Approved
0.7054	Intermediate Similarity	NPD4634	Approved
0.7054	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5135	Approved
0.7033	Intermediate Similarity	NPD4691	Approved
0.703	Intermediate Similarity	NPD4518	Approved
0.7027	Intermediate Similarity	NPD5128	Approved
0.7018	Intermediate Similarity	NPD4632	Approved
0.7009	Intermediate Similarity	NPD7101	Approved
0.7009	Intermediate Similarity	NPD7100	Approved
0.6991	Remote Similarity	NPD5127	Approved
0.6991	Remote Similarity	NPD5215	Approved
0.6991	Remote Similarity	NPD5216	Approved
0.6991	Remote Similarity	NPD5217	Approved
0.699	Remote Similarity	NPD7515	Phase 2
0.6989	Remote Similarity	NPD4687	Approved
0.6989	Remote Similarity	NPD5733	Approved
0.6989	Remote Similarity	NPD4785	Approved
0.6989	Remote Similarity	NPD4784	Approved
0.6989	Remote Similarity	NPD4058	Approved
0.6983	Remote Similarity	NPD6317	Approved
0.6981	Remote Similarity	NPD5959	Approved
0.6972	Remote Similarity	NPD6052	Approved
0.6952	Remote Similarity	NPD5654	Approved
0.6949	Remote Similarity	NPD6054	Approved
0.6937	Remote Similarity	NPD6614	Approved
0.6937	Remote Similarity	NPD6412	Phase 2
0.693	Remote Similarity	NPD6053	Discontinued
0.6923	Remote Similarity	NPD6314	Approved
0.6923	Remote Similarity	NPD5133	Approved
0.6923	Remote Similarity	NPD6313	Approved
0.6917	Remote Similarity	NPD7604	Phase 2
0.6917	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6274	Approved
0.6893	Remote Similarity	NPD4096	Approved
0.6893	Remote Similarity	NPD5785	Approved
0.6881	Remote Similarity	NPD7632	Discontinued
0.6875	Remote Similarity	NPD3617	Approved
0.6842	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6009	Approved
0.6837	Remote Similarity	NPD4692	Approved
0.6837	Remote Similarity	NPD4139	Approved
0.6833	Remote Similarity	NPD6370	Approved
0.6827	Remote Similarity	NPD8034	Phase 2
0.6827	Remote Similarity	NPD8035	Phase 2
0.6814	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5167	Approved
0.6807	Remote Similarity	NPD6059	Approved
0.6807	Remote Similarity	NPD6319	Approved
0.6803	Remote Similarity	NPD7507	Approved
0.6774	Remote Similarity	NPD4243	Approved
0.6774	Remote Similarity	NPD5276	Approved
0.6765	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6868	Approved
0.675	Remote Similarity	NPD6015	Approved
0.675	Remote Similarity	NPD6909	Approved
0.675	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5983	Phase 2
0.675	Remote Similarity	NPD6016	Approved
0.675	Remote Similarity	NPD6908	Approved
0.6737	Remote Similarity	NPD6942	Approved
0.6737	Remote Similarity	NPD7339	Approved
0.6735	Remote Similarity	NPD4695	Discontinued
0.6735	Remote Similarity	NPD7525	Registered
0.6733	Remote Similarity	NPD7520	Clinical (unspecified phase)

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