NPASS Compound

Structure

CID257296 OpenBabel06191716062D 30 35 0 0 1 0 0 0 0 0999 V2000 3.5827 -0.7834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3104 -2.5222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4137 -3.7052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8950 -2.2523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1181 -1.7501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2783 -1.2659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0760 -1.6533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1192 -4.6572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6010 -3.2053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2798 -4.1735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7613 -2.7211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0714 -1.6533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9581 -3.2032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7596 0.1856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0760 0.0865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5782 -0.7834 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.5668 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1186 -2.7195 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9584 -4.1720 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4391 -1.7511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4397 -2.7204 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5994 -1.2669 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9209 -0.2992 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9209 -1.2676 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2795 -3.2046 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7607 -1.7518 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5692 -0.7834 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8246 -4.6716 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0714 0.0865 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 2 17 1 0 0 0 0 5 6 1 0 0 0 0 5 18 1 0 0 0 0 7 12 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 21 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 29 1 0 0 0 0 16 1 1 1 0 0 0 17 24 1 0 0 0 0 17 27 1 1 0 0 0 18 25 1 6 0 0 0 19 28 1 6 0 0 0 20 6 1 1 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 25 1 6 0 0 0 22 26 1 6 0 0 0 23 14 1 6 0 0 0 23 24 1 0 0 0 0 23 30 1 0 0 0 0 24 26 1 6 0 0 0 25 3 1 6 0 0 0 26 4 1 6 0 0 0 27 12 1 6 0 0 0 27 29 1 0 0 0 0 27 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.33
Volume:	450.58
LogP:	6.281
LogD:	5.094
LogS:	-5.391
# Rotatable Bonds:	0
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.543
Synthetic Accessibility Score:	5.22
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.74
MDCK Permeability:	1.663502916926518e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.702
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.904
30% Bioavailability (F30%):	0.447

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.284
Plasma Protein Binding (PPB):	84.85637664794922%
Volume Distribution (VD):	1.604
Pgp-substrate:	3.585200309753418%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.485
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.746
CYP2C9-inhibitor:	0.201
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.732
CYP3A4-substrate:	0.249

ADMET: Excretion

Clearance (CL):	18.296
Half-life (T1/2):	0.114

ADMET: Toxicity

hERG Blockers:	0.995
Human Hepatotoxicity (H-HT):	0.236
Drug-inuced Liver Injury (DILI):	0.797
AMES Toxicity:	0.152
Rat Oral Acute Toxicity:	0.111
Maximum Recommended Daily Dose:	0.746
Skin Sensitization:	0.98
Carcinogencity:	0.528
Eye Corrosion:	0.971
Eye Irritation:	0.586
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC257296

Natural Product ID:	NPC257296
*Common Name:**	GMBQZIIUCVWOCD-PUHUBZITSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GMBQZIIUCVWOCD-PUHUBZITSA-N
Standard InCHI:	InChI=1S/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26-,27+/m0/s1
SMILES:	C[C@H]1CC[C@@]2(OC1)O[C@@H]1[C@H]([C@@H]2C)[C@@]2([C@@H](C1)[C@@H]1CC[C@@H]3[C@]([C@H]1CC2)(C)CC[C@@H](C3)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3808706
PubChem CID:	12304433
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374966]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11599360]
NPO22917	Flustra foliacea	Species	Flustridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444689]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO22917	Flustra foliacea	Species	Flustridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19785389]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381697]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29185738]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30351923]
NPO22917	Flustra foliacea	Species	Flustridae	Eukaryota	n.a.	n.a.	n.a.	PMID[33016699]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO22917	Flustra foliacea	Species	Flustridae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964794]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO14899	Agave sisalana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23541	Smilax sieboldii	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1530	Agave cantala	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8976.1	Agave americana var. marginata	Varieties	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22917	Flustra foliacea	Species	Flustridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8976.1	Agave americana var. marginata	Varieties	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22917	Flustra foliacea	Species	Flustridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14899	Agave sisalana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1530	Agave cantala	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23541	Smilax sieboldii	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15634	Radix smilacis	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14899	Agave sisalana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23541	Smilax sieboldii	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22917	Flustra foliacea	Species	Flustridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14899	Agave sisalana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1530	Agave cantala	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24936	Mentha asiatica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23658	Paeonia hybr	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23541	Smilax sieboldii	Species	Smilacaceae	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	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[450689]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[450689]
NPT1872	Cell Line	Bcap37	Homo sapiens	IC50	>	50000.0	nM	PMID[450689]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[450689]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[450689]

☑ 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 NPC257296 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	453
0.1-0.2	4780
0.2-0.3	15847
0.3-0.4	9284
0.4-0.5	4972
0.5-0.6	4428
0.6-0.7	2092
0.7-0.8	637
0.8-0.85	118
0.85-0.9	77
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC248944
1.0	High Similarity	NPC7479
0.9737	High Similarity	NPC296734
0.9487	High Similarity	NPC227260
0.9367	High Similarity	NPC232044
0.9367	High Similarity	NPC273290
0.9231	High Similarity	NPC470611
0.881	High Similarity	NPC473542
0.8706	High Similarity	NPC149966
0.8706	High Similarity	NPC59006
0.8706	High Similarity	NPC5632
0.869	High Similarity	NPC228059
0.8675	High Similarity	NPC161928
0.8675	High Similarity	NPC210658
0.8605	High Similarity	NPC144790
0.8605	High Similarity	NPC234352
0.8605	High Similarity	NPC161035
0.8605	High Similarity	NPC177834
0.8605	High Similarity	NPC48339
0.8605	High Similarity	NPC477547
0.8605	High Similarity	NPC141769
0.8605	High Similarity	NPC88962
0.8605	High Similarity	NPC167644
0.8605	High Similarity	NPC250393
0.8605	High Similarity	NPC477451
0.8605	High Similarity	NPC149400
0.8605	High Similarity	NPC311246
0.8605	High Similarity	NPC249204
0.8605	High Similarity	NPC325828
0.8605	High Similarity	NPC297348
0.8571	High Similarity	NPC281004
0.8571	High Similarity	NPC128475
0.8554	High Similarity	NPC471240
0.8506	High Similarity	NPC477224
0.8506	High Similarity	NPC24960
0.8506	High Similarity	NPC30687
0.8506	High Similarity	NPC222731
0.8506	High Similarity	NPC174024
0.8506	High Similarity	NPC475436
0.8506	High Similarity	NPC3538
0.8506	High Similarity	NPC253268
0.8506	High Similarity	NPC179859
0.8506	High Similarity	NPC312678
0.8506	High Similarity	NPC45959
0.8506	High Similarity	NPC113500
0.8506	High Similarity	NPC473851
0.8506	High Similarity	NPC217205
0.8506	High Similarity	NPC291547
0.8506	High Similarity	NPC291203
0.8506	High Similarity	NPC252253
0.8506	High Similarity	NPC131693
0.8506	High Similarity	NPC294686
0.8506	High Similarity	NPC471464
0.8506	High Similarity	NPC473774
0.8506	High Similarity	NPC264101
0.8506	High Similarity	NPC175
0.8471	Intermediate Similarity	NPC82955
0.8471	Intermediate Similarity	NPC473472
0.8471	Intermediate Similarity	NPC102725
0.8471	Intermediate Similarity	NPC20822
0.8434	Intermediate Similarity	NPC290612
0.8415	Intermediate Similarity	NPC470070
0.8409	Intermediate Similarity	NPC6295
0.8409	Intermediate Similarity	NPC19400
0.8409	Intermediate Similarity	NPC107188
0.8409	Intermediate Similarity	NPC473610
0.8409	Intermediate Similarity	NPC473065
0.8409	Intermediate Similarity	NPC107962
0.8409	Intermediate Similarity	NPC473067
0.8409	Intermediate Similarity	NPC473064
0.8409	Intermediate Similarity	NPC473727
0.8409	Intermediate Similarity	NPC305808
0.8409	Intermediate Similarity	NPC206003
0.8409	Intermediate Similarity	NPC211354
0.8409	Intermediate Similarity	NPC474399
0.8409	Intermediate Similarity	NPC475351
0.84	Intermediate Similarity	NPC477820
0.8372	Intermediate Similarity	NPC223143
0.8372	Intermediate Similarity	NPC65550
0.8372	Intermediate Similarity	NPC279329
0.8354	Intermediate Similarity	NPC476233
0.8315	Intermediate Similarity	NPC470864
0.8315	Intermediate Similarity	NPC195297
0.8315	Intermediate Similarity	NPC84111
0.8315	Intermediate Similarity	NPC132080
0.8315	Intermediate Similarity	NPC98018
0.8315	Intermediate Similarity	NPC470863
0.8315	Intermediate Similarity	NPC103616
0.8315	Intermediate Similarity	NPC287483
0.8315	Intermediate Similarity	NPC284104
0.8315	Intermediate Similarity	NPC304011
0.8315	Intermediate Similarity	NPC470866
0.8315	Intermediate Similarity	NPC184617
0.8315	Intermediate Similarity	NPC475643
0.8315	Intermediate Similarity	NPC97700
0.8315	Intermediate Similarity	NPC30856
0.8315	Intermediate Similarity	NPC476510
0.8315	Intermediate Similarity	NPC470865
0.8315	Intermediate Similarity	NPC139271
0.8315	Intermediate Similarity	NPC121453
0.8315	Intermediate Similarity	NPC473601
0.8315	Intermediate Similarity	NPC142264
0.8315	Intermediate Similarity	NPC232037
0.8315	Intermediate Similarity	NPC160426
0.8315	Intermediate Similarity	NPC156377
0.8315	Intermediate Similarity	NPC475625
0.8315	Intermediate Similarity	NPC116756
0.8315	Intermediate Similarity	NPC128572
0.8293	Intermediate Similarity	NPC24556
0.8289	Intermediate Similarity	NPC282454
0.8289	Intermediate Similarity	NPC251201
0.8289	Intermediate Similarity	NPC232925
0.8289	Intermediate Similarity	NPC63588
0.8276	Intermediate Similarity	NPC307167
0.8276	Intermediate Similarity	NPC204881
0.8276	Intermediate Similarity	NPC210759
0.8276	Intermediate Similarity	NPC473830
0.8276	Intermediate Similarity	NPC36372
0.8276	Intermediate Similarity	NPC473637
0.8276	Intermediate Similarity	NPC229801
0.8276	Intermediate Similarity	NPC293609
0.8276	Intermediate Similarity	NPC476668
0.8235	Intermediate Similarity	NPC140446
0.8235	Intermediate Similarity	NPC43912
0.8222	Intermediate Similarity	NPC83137
0.8222	Intermediate Similarity	NPC274200
0.8222	Intermediate Similarity	NPC233649
0.8222	Intermediate Similarity	NPC477222
0.8222	Intermediate Similarity	NPC476112
0.8222	Intermediate Similarity	NPC115165
0.8222	Intermediate Similarity	NPC51520
0.8222	Intermediate Similarity	NPC475207
0.8222	Intermediate Similarity	NPC303069
0.8222	Intermediate Similarity	NPC470862
0.8222	Intermediate Similarity	NPC477223
0.8222	Intermediate Similarity	NPC232611
0.8222	Intermediate Similarity	NPC470028
0.8222	Intermediate Similarity	NPC470861
0.8222	Intermediate Similarity	NPC307534
0.8205	Intermediate Similarity	NPC477508
0.8182	Intermediate Similarity	NPC277774
0.8182	Intermediate Similarity	NPC1340
0.8182	Intermediate Similarity	NPC242419
0.8182	Intermediate Similarity	NPC122083
0.8182	Intermediate Similarity	NPC476669
0.8182	Intermediate Similarity	NPC252182
0.8182	Intermediate Similarity	NPC157422
0.8182	Intermediate Similarity	NPC470071
0.8182	Intermediate Similarity	NPC473726
0.8182	Intermediate Similarity	NPC100586
0.8182	Intermediate Similarity	NPC109457
0.8182	Intermediate Similarity	NPC182740
0.8182	Intermediate Similarity	NPC172838
0.8182	Intermediate Similarity	NPC187471
0.8182	Intermediate Similarity	NPC235126
0.8182	Intermediate Similarity	NPC137004
0.8182	Intermediate Similarity	NPC211845
0.8182	Intermediate Similarity	NPC256104
0.8148	Intermediate Similarity	NPC476176
0.8132	Intermediate Similarity	NPC291548
0.8132	Intermediate Similarity	NPC473518
0.8132	Intermediate Similarity	NPC473638
0.8132	Intermediate Similarity	NPC473616
0.8125	Intermediate Similarity	NPC474574
0.8125	Intermediate Similarity	NPC64081
0.8101	Intermediate Similarity	NPC270306
0.8101	Intermediate Similarity	NPC231680
0.8101	Intermediate Similarity	NPC91387
0.8095	Intermediate Similarity	NPC474156
0.809	Intermediate Similarity	NPC473503
0.809	Intermediate Similarity	NPC475325
0.809	Intermediate Similarity	NPC309866
0.809	Intermediate Similarity	NPC305418
0.8077	Intermediate Similarity	NPC470610
0.8072	Intermediate Similarity	NPC475388
0.8046	Intermediate Similarity	NPC131466
0.8043	Intermediate Similarity	NPC470030
0.8025	Intermediate Similarity	NPC477577
0.8025	Intermediate Similarity	NPC471045
0.8023	Intermediate Similarity	NPC472396
0.8	Intermediate Similarity	NPC469710
0.8	Intermediate Similarity	NPC92196
0.8	Intermediate Similarity	NPC44122
0.8	Intermediate Similarity	NPC21897
0.7976	Intermediate Similarity	NPC474284
0.7976	Intermediate Similarity	NPC475820
0.7976	Intermediate Similarity	NPC213737
0.7976	Intermediate Similarity	NPC474346
0.7976	Intermediate Similarity	NPC474253
0.7975	Intermediate Similarity	NPC48795
0.7975	Intermediate Similarity	NPC304499
0.7973	Intermediate Similarity	NPC167995
0.7973	Intermediate Similarity	NPC281540
0.7973	Intermediate Similarity	NPC118937
0.7973	Intermediate Similarity	NPC159654
0.7957	Intermediate Similarity	NPC475574
0.7957	Intermediate Similarity	NPC476512
0.7957	Intermediate Similarity	NPC472081
0.7957	Intermediate Similarity	NPC108227
0.7957	Intermediate Similarity	NPC477225

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 NPC257296 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	450
0.1-0.2	4509
0.2-0.3	3020
0.3-0.4	631
0.4-0.5	252
0.5-0.6	212
0.6-0.7	70
0.7-0.8	3
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD6928	Phase 2
0.8605	High Similarity	NPD8171	Discontinued
0.8202	Intermediate Similarity	NPD7991	Discontinued
0.7708	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4787	Phase 1
0.725	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6118	Approved
0.7176	Intermediate Similarity	NPD6115	Approved
0.7176	Intermediate Similarity	NPD6114	Approved
0.7176	Intermediate Similarity	NPD6697	Approved
0.7108	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6116	Phase 1
0.6951	Remote Similarity	NPD4244	Approved
0.6951	Remote Similarity	NPD4245	Approved
0.6941	Remote Similarity	NPD6117	Approved
0.6829	Remote Similarity	NPD3698	Phase 2
0.6829	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3703	Phase 2
0.6824	Remote Similarity	NPD3702	Approved
0.6706	Remote Similarity	NPD1810	Approved
0.6706	Remote Similarity	NPD1811	Approved
0.6697	Remote Similarity	NPD7328	Approved
0.6697	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD5777	Approved
0.6636	Remote Similarity	NPD7516	Approved
0.6629	Remote Similarity	NPD7525	Registered
0.6577	Remote Similarity	NPD8294	Approved
0.6577	Remote Similarity	NPD8377	Approved
0.6548	Remote Similarity	NPD4789	Approved
0.6538	Remote Similarity	NPD6412	Phase 2
0.6518	Remote Similarity	NPD8033	Approved
0.6518	Remote Similarity	NPD8380	Approved
0.6518	Remote Similarity	NPD8379	Approved
0.6518	Remote Similarity	NPD8296	Approved
0.6518	Remote Similarity	NPD8335	Approved
0.6518	Remote Similarity	NPD8378	Approved
0.6506	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD5360	Phase 3
0.6481	Remote Similarity	NPD8133	Approved
0.6452	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD8034	Phase 2
0.6392	Remote Similarity	NPD8035	Phase 2
0.6364	Remote Similarity	NPD6940	Discontinued
0.6364	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD2254	Approved
0.6353	Remote Similarity	NPD2686	Approved
0.6353	Remote Similarity	NPD2687	Approved
0.6341	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7638	Approved
0.6321	Remote Similarity	NPD8174	Phase 2
0.6293	Remote Similarity	NPD7507	Approved
0.6283	Remote Similarity	NPD6054	Approved
0.6283	Remote Similarity	NPD6059	Approved
0.6275	Remote Similarity	NPD7639	Approved
0.6275	Remote Similarity	NPD7640	Approved
0.6264	Remote Similarity	NPD4748	Discontinued
0.625	Remote Similarity	NPD7339	Approved
0.625	Remote Similarity	NPD6942	Approved
0.6222	Remote Similarity	NPD3671	Phase 1
0.622	Remote Similarity	NPD371	Approved
0.6211	Remote Similarity	NPD8308	Discontinued
0.6186	Remote Similarity	NPD7736	Approved
0.6174	Remote Similarity	NPD6370	Approved
0.6163	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7645	Phase 2
0.6154	Remote Similarity	NPD7632	Discontinued
0.6146	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD7319	Approved
0.6122	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6700	Approved
0.6118	Remote Similarity	NPD6705	Phase 1
0.6092	Remote Similarity	NPD4758	Discontinued
0.6092	Remote Similarity	NPD6081	Approved
0.6087	Remote Similarity	NPD6015	Approved
0.6087	Remote Similarity	NPD6016	Approved
0.6087	Remote Similarity	NPD7503	Approved
0.6071	Remote Similarity	NPD4224	Phase 2
0.6068	Remote Similarity	NPD7492	Approved
0.6064	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4788	Approved
0.6064	Remote Similarity	NPD3669	Approved
0.6061	Remote Similarity	NPD6703	Approved
0.6061	Remote Similarity	NPD6702	Approved
0.6034	Remote Similarity	NPD5988	Approved
0.6017	Remote Similarity	NPD6616	Approved
0.6	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD6067	Discontinued
0.5966	Remote Similarity	NPD8293	Discontinued
0.5966	Remote Similarity	NPD7078	Approved
0.5963	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6882	Approved
0.5926	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD6033	Approved
0.5909	Remote Similarity	NPD4243	Approved
0.5905	Remote Similarity	NPD1700	Approved
0.5895	Remote Similarity	NPD6695	Phase 3
0.5877	Remote Similarity	NPD6009	Approved
0.5872	Remote Similarity	NPD7320	Approved
0.587	Remote Similarity	NPD4238	Approved
0.587	Remote Similarity	NPD4802	Phase 2
0.587	Remote Similarity	NPD5364	Discontinued
0.5854	Remote Similarity	NPD8449	Approved
0.5842	Remote Similarity	NPD4202	Approved
0.5842	Remote Similarity	NPD6399	Phase 3
0.5833	Remote Similarity	NPD6675	Approved
0.5833	Remote Similarity	NPD6008	Approved
0.5833	Remote Similarity	NPD5739	Approved
0.5833	Remote Similarity	NPD7128	Approved
0.5833	Remote Similarity	NPD4786	Approved
0.5833	Remote Similarity	NPD6402	Approved
0.581	Remote Similarity	NPD8418	Phase 2
0.5806	Remote Similarity	NPD8450	Suspended
0.5806	Remote Similarity	NPD6929	Approved
0.5789	Remote Similarity	NPD7754	Approved
0.5789	Remote Similarity	NPD7755	Approved
0.5778	Remote Similarity	NPD6926	Approved
0.5778	Remote Similarity	NPD6924	Approved
0.5778	Remote Similarity	NPD4785	Approved
0.5778	Remote Similarity	NPD4784	Approved
0.5758	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD6931	Approved
0.5745	Remote Similarity	NPD6930	Phase 2
0.5739	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6899	Approved
0.5727	Remote Similarity	NPD6881	Approved
0.57	Remote Similarity	NPD5328	Approved
0.5688	Remote Similarity	NPD6920	Discontinued
0.5676	Remote Similarity	NPD6373	Approved
0.5676	Remote Similarity	NPD6372	Approved
0.567	Remote Similarity	NPD3133	Approved
0.567	Remote Similarity	NPD3665	Phase 1
0.567	Remote Similarity	NPD3666	Approved
0.5657	Remote Similarity	NPD7750	Discontinued
0.5657	Remote Similarity	NPD7524	Approved
0.5652	Remote Similarity	NPD6933	Approved
0.5636	Remote Similarity	NPD5697	Approved
0.5636	Remote Similarity	NPD5701	Approved
0.5625	Remote Similarity	NPD6883	Approved
0.5625	Remote Similarity	NPD7290	Approved
0.5625	Remote Similarity	NPD7102	Approved
0.5625	Remote Similarity	NPD3667	Approved
0.5619	Remote Similarity	NPD4755	Approved
0.5619	Remote Similarity	NPD6084	Phase 2
0.5619	Remote Similarity	NPD6083	Phase 2
0.5614	Remote Similarity	NPD4632	Approved
0.56	Remote Similarity	NPD385	Approved
0.56	Remote Similarity	NPD384	Approved
0.56	Remote Similarity	NPD6903	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