NPASS Compound

Structure

CID312637 OpenBabel06191716122D 31 35 0 0 1 0 0 0 0 0999 V2000 6.5218 4.6233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6247 0.5746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4136 0.9593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8766 -0.5061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1686 1.2620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9780 3.9360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3823 2.9295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5370 3.4175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4045 3.1466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8453 -1.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6912 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5370 0.4887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6914 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3452 2.9427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9484 3.8340 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2279 1.4659 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6911 -0.9757 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8459 1.4651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3829 1.9538 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6917 1.9535 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8459 0.4884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8458 0.4883 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8014 2.2553 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8458 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5370 1.4654 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7717 2.1533 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5571 -1.4757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7118 1.9651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 29 1 0 0 0 0 6 9 1 0 0 0 0 6 17 1 0 0 0 0 7 8 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 25 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 28 1 0 0 0 0 13 27 1 0 0 0 0 14 19 1 0 0 0 0 14 24 1 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 16 29 1 0 0 0 0 17 1 1 1 0 0 0 18 2 1 1 0 0 0 18 21 1 0 0 0 0 19 30 1 6 0 0 0 20 15 1 1 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 27 1 1 0 0 0 22 27 1 6 0 0 0 23 28 1 6 0 0 0 24 26 1 0 0 0 0 24 28 1 6 0 0 0 25 18 1 6 0 0 0 25 29 1 0 0 0 0 26 31 2 0 0 0 0 27 3 1 6 0 0 0 28 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	429.36
Volume:	476.003
LogP:	5.235
LogD:	4.762
LogS:	-4.405
# Rotatable Bonds:	2
TPSA:	40.54
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.625
Synthetic Accessibility Score:	4.791
Fsp3:	0.964
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:	-4.726
MDCK Permeability:	1.1368587365723215e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.806
30% Bioavailability (F30%):	0.67

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.703
Plasma Protein Binding (PPB):	72.24365234375%
Volume Distribution (VD):	2.277
Pgp-substrate:	8.963756561279297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.231
CYP2C19-inhibitor:	0.058
CYP2C19-substrate:	0.956
CYP2C9-inhibitor:	0.107
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.822
CYP2D6-substrate:	0.865
CYP3A4-inhibitor:	0.788
CYP3A4-substrate:	0.775

ADMET: Excretion

Clearance (CL):	20.761
Half-life (T1/2):	0.077

ADMET: Toxicity

hERG Blockers:	0.975
Human Hepatotoxicity (H-HT):	0.374
Drug-inuced Liver Injury (DILI):	0.85
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.847
Maximum Recommended Daily Dose:	0.868
Skin Sensitization:	0.954
Carcinogencity:	0.472
Eye Corrosion:	0.962
Eye Irritation:	0.058
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC312637

Natural Product ID:	NPC312637
*Common Name:**	Puqietinone
IUPAC Name:	(3S,5S,8S,9S,10R,13S,14S,17S)-17-[(1S)-1-[(2S,5R)-1,5-dimethylpiperidin-2-yl]ethyl]-3-hydroxy-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
Synonyms:	Puqietinone
Standard InCHIKey:	HEOBUSMYCWXIQQ-OXZWOSNHSA-N
Standard InCHI:	InChI=1S/C28H47NO2/c1-17-6-9-25(29(5)16-17)18(2)21-7-8-22-20-15-26(31)24-14-19(30)10-12-28(24,4)23(20)11-13-27(21,22)3/h17-25,30H,6-16H2,1-5H3/t17-,18+,19+,20+,21+,22+,23+,24-,25+,27-,28-/m1/s1
SMILES:	C[C@@H]1CC[C@@H]([C@@H](C)[C@@H]2CC[C@H]3[C@@H]4CC(=O)[C@H]5C[C@H](CC[C@]5(C)[C@H]4CC[C@]23C)O)N(C)C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498633
PubChem CID:	44583920
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002724] Steroidal alkaloids [CHEMONTID:0002732] 22,26-epiminocholestanes

*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
NPO20194	Fritillaria puqiensis	Species	Liliaceae	Eukaryota	bulbs	n.a.	n.a.	PMID[15730259]
NPO22292	Fritillaria przewalskii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20194	Fritillaria puqiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18644	Fritillaria walujewii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1279	Fritillaria cirrhosa	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7844	Fritillaria hupehensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14849	Fritillaria unibracteata	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12273	Fritillaria delavayi	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1279	Fritillaria cirrhosa	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20194	Fritillaria puqiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18644	Fritillaria walujewii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14849	Fritillaria unibracteata	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22292	Fritillaria przewalskii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7844	Fritillaria hupehensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12273	Fritillaria delavayi	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22292	Fritillaria przewalskii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14849	Fritillaria unibracteata	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12556	Fritillaria verticillata	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18644	Fritillaria walujewii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12273	Fritillaria delavayi	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1279	Fritillaria cirrhosa	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7844	Fritillaria hupehensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25808	Fritillaria taipaiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18644	Fritillaria walujewii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12273	Fritillaria delavayi	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14135	Fritillaria prezewalskii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12556	Fritillaria verticillata	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14849	Fritillaria unibracteata	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22292	Fritillaria przewalskii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7844	Fritillaria hupehensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22292	Fritillaria przewalskii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1279	Fritillaria cirrhosa	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12556	Fritillaria verticillata	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20194	Fritillaria puqiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25808	Fritillaria taipaiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14849	Fritillaria unibracteata	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18644	Fritillaria walujewii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12273	Fritillaria delavayi	Species	Liliaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	11.0	n.a.	PMID[475582]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	17.0	n.a.	PMID[475582]

☑ 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 NPC312637 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	139
0.1-0.2	1961
0.2-0.3	16876
0.3-0.4	11364
0.4-0.5	6217
0.5-0.6	4744
0.6-0.7	1206
0.7-0.8	173
0.8-0.85	13
0.85-0.9	0
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9326	High Similarity	NPC174117
0.9231	High Similarity	NPC220111
0.8557	High Similarity	NPC475239
0.8077	Intermediate Similarity	NPC28224
0.8068	Intermediate Similarity	NPC109533
0.7857	Intermediate Similarity	NPC156277
0.7857	Intermediate Similarity	NPC58057
0.7857	Intermediate Similarity	NPC151018
0.7857	Intermediate Similarity	NPC320549
0.7816	Intermediate Similarity	NPC23884
0.78	Intermediate Similarity	NPC470592
0.7791	Intermediate Similarity	NPC97534
0.7791	Intermediate Similarity	NPC174964
0.7791	Intermediate Similarity	NPC195155
0.7765	Intermediate Similarity	NPC232112
0.7701	Intermediate Similarity	NPC5767
0.7701	Intermediate Similarity	NPC472487
0.7701	Intermediate Similarity	NPC472486
0.7701	Intermediate Similarity	NPC475742
0.7674	Intermediate Similarity	NPC254340
0.7647	Intermediate Similarity	NPC89310
0.7624	Intermediate Similarity	NPC476755
0.7619	Intermediate Similarity	NPC213178
0.7619	Intermediate Similarity	NPC6120
0.7619	Intermediate Similarity	NPC327728
0.7619	Intermediate Similarity	NPC131892
0.7614	Intermediate Similarity	NPC221420
0.7586	Intermediate Similarity	NPC21220
0.7586	Intermediate Similarity	NPC125767
0.7586	Intermediate Similarity	NPC273366
0.7576	Intermediate Similarity	NPC292819
0.7524	Intermediate Similarity	NPC473994
0.7475	Intermediate Similarity	NPC289140
0.7471	Intermediate Similarity	NPC167702
0.7471	Intermediate Similarity	NPC280026
0.7416	Intermediate Similarity	NPC298168
0.7416	Intermediate Similarity	NPC475031
0.7416	Intermediate Similarity	NPC143133
0.7396	Intermediate Similarity	NPC135005
0.7386	Intermediate Similarity	NPC212733
0.7374	Intermediate Similarity	NPC155985
0.7363	Intermediate Similarity	NPC470609
0.7356	Intermediate Similarity	NPC310766
0.7333	Intermediate Similarity	NPC185465
0.7315	Intermediate Similarity	NPC124358
0.7303	Intermediate Similarity	NPC4209
0.7283	Intermediate Similarity	NPC192456
0.7273	Intermediate Similarity	NPC159325
0.7273	Intermediate Similarity	NPC168511
0.7273	Intermediate Similarity	NPC133922
0.7253	Intermediate Similarity	NPC320144
0.7234	Intermediate Similarity	NPC475745
0.7234	Intermediate Similarity	NPC474482
0.7222	Intermediate Similarity	NPC207010
0.7222	Intermediate Similarity	NPC317913
0.7209	Intermediate Similarity	NPC324607
0.7209	Intermediate Similarity	NPC321732
0.7204	Intermediate Similarity	NPC328007
0.7204	Intermediate Similarity	NPC289486
0.7204	Intermediate Similarity	NPC317066
0.7204	Intermediate Similarity	NPC30583
0.7204	Intermediate Similarity	NPC61107
0.7191	Intermediate Similarity	NPC159789
0.717	Intermediate Similarity	NPC476756
0.717	Intermediate Similarity	NPC244982
0.7159	Intermediate Similarity	NPC282905
0.7159	Intermediate Similarity	NPC477229
0.7159	Intermediate Similarity	NPC68426
0.7143	Intermediate Similarity	NPC224802
0.7143	Intermediate Similarity	NPC34046
0.7143	Intermediate Similarity	NPC324700
0.7143	Intermediate Similarity	NPC80089
0.7143	Intermediate Similarity	NPC171426
0.7128	Intermediate Similarity	NPC472743
0.7128	Intermediate Similarity	NPC475726
0.7111	Intermediate Similarity	NPC108840
0.7105	Intermediate Similarity	NPC238323
0.7097	Intermediate Similarity	NPC58631
0.7097	Intermediate Similarity	NPC469745
0.7093	Intermediate Similarity	NPC473225
0.7083	Intermediate Similarity	NPC472738
0.7079	Intermediate Similarity	NPC472854
0.7079	Intermediate Similarity	NPC130011
0.7065	Intermediate Similarity	NPC201276
0.7065	Intermediate Similarity	NPC80891
0.7054	Intermediate Similarity	NPC39485
0.7054	Intermediate Similarity	NPC221196
0.7053	Intermediate Similarity	NPC474996
0.7053	Intermediate Similarity	NPC474233
0.7045	Intermediate Similarity	NPC473267
0.7033	Intermediate Similarity	NPC264602
0.7027	Intermediate Similarity	NPC135431
0.7021	Intermediate Similarity	NPC268040
0.7011	Intermediate Similarity	NPC319671
0.7011	Intermediate Similarity	NPC476734
0.7011	Intermediate Similarity	NPC469941
0.7011	Intermediate Similarity	NPC252032
0.7009	Intermediate Similarity	NPC83047
0.7009	Intermediate Similarity	NPC267217
0.7009	Intermediate Similarity	NPC48127
0.7009	Intermediate Similarity	NPC8009
0.7	Intermediate Similarity	NPC267753
0.699	Remote Similarity	NPC91604
0.6989	Remote Similarity	NPC261616
0.6981	Remote Similarity	NPC470596
0.6979	Remote Similarity	NPC292553
0.6966	Remote Similarity	NPC81759
0.6964	Remote Similarity	NPC209252
0.6957	Remote Similarity	NPC329117
0.6947	Remote Similarity	NPC323180
0.6947	Remote Similarity	NPC327451
0.6947	Remote Similarity	NPC472744
0.6939	Remote Similarity	NPC472739
0.6939	Remote Similarity	NPC474719
0.6932	Remote Similarity	NPC476731
0.6932	Remote Similarity	NPC477929
0.6932	Remote Similarity	NPC108131
0.693	Remote Similarity	NPC475340
0.6915	Remote Similarity	NPC12933
0.6915	Remote Similarity	NPC50658
0.6909	Remote Similarity	NPC34977
0.6909	Remote Similarity	NPC246399
0.6905	Remote Similarity	NPC114891
0.6897	Remote Similarity	NPC474954
0.6897	Remote Similarity	NPC180777
0.6897	Remote Similarity	NPC103647
0.6897	Remote Similarity	NPC2568
0.6897	Remote Similarity	NPC260319
0.6893	Remote Similarity	NPC473537
0.6893	Remote Similarity	NPC474164
0.6887	Remote Similarity	NPC98765
0.6882	Remote Similarity	NPC201459
0.6875	Remote Similarity	NPC473336
0.6875	Remote Similarity	NPC471044
0.6875	Remote Similarity	NPC50438
0.6875	Remote Similarity	NPC74595
0.6875	Remote Similarity	NPC264665
0.6875	Remote Similarity	NPC175419
0.686	Remote Similarity	NPC142712
0.6854	Remote Similarity	NPC126642
0.6852	Remote Similarity	NPC46981
0.6842	Remote Similarity	NPC121121
0.6837	Remote Similarity	NPC57469
0.6837	Remote Similarity	NPC4643
0.6837	Remote Similarity	NPC21035
0.6832	Remote Similarity	NPC161035
0.6827	Remote Similarity	NPC475249
0.6827	Remote Similarity	NPC252564
0.6818	Remote Similarity	NPC139778
0.6814	Remote Similarity	NPC476502
0.6813	Remote Similarity	NPC472311
0.6813	Remote Similarity	NPC27349
0.6813	Remote Similarity	NPC24014
0.6809	Remote Similarity	NPC164999
0.6809	Remote Similarity	NPC477851
0.6804	Remote Similarity	NPC264317
0.6804	Remote Similarity	NPC76518
0.6804	Remote Similarity	NPC294438
0.6804	Remote Similarity	NPC34811
0.6792	Remote Similarity	NPC176012
0.6789	Remote Similarity	NPC470595
0.6786	Remote Similarity	NPC71460
0.6786	Remote Similarity	NPC218585
0.6786	Remote Similarity	NPC148174
0.6782	Remote Similarity	NPC472984
0.6782	Remote Similarity	NPC48079
0.6777	Remote Similarity	NPC478139
0.6774	Remote Similarity	NPC472608
0.6774	Remote Similarity	NPC26029
0.6768	Remote Similarity	NPC90676
0.6762	Remote Similarity	NPC201712
0.675	Remote Similarity	NPC212106
0.6742	Remote Similarity	NPC477850
0.6742	Remote Similarity	NPC282454
0.6737	Remote Similarity	NPC48756
0.6737	Remote Similarity	NPC474484
0.6737	Remote Similarity	NPC280781
0.6737	Remote Similarity	NPC103754
0.6735	Remote Similarity	NPC80700
0.6735	Remote Similarity	NPC98236
0.6735	Remote Similarity	NPC12774
0.6735	Remote Similarity	NPC171698
0.6735	Remote Similarity	NPC476726
0.6735	Remote Similarity	NPC269396
0.6735	Remote Similarity	NPC119633
0.6735	Remote Similarity	NPC321340
0.6735	Remote Similarity	NPC476727
0.6735	Remote Similarity	NPC2783
0.6735	Remote Similarity	NPC270957
0.6705	Remote Similarity	NPC472741
0.6703	Remote Similarity	NPC477930
0.6702	Remote Similarity	NPC472310
0.6702	Remote Similarity	NPC245029
0.6702	Remote Similarity	NPC31302
0.6702	Remote Similarity	NPC52951
0.6701	Remote Similarity	NPC25037
0.6701	Remote Similarity	NPC146683
0.6701	Remote Similarity	NPC319909
0.6701	Remote Similarity	NPC34984
0.67	Remote Similarity	NPC122116

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 NPC312637 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	97
0.1-0.2	1408
0.2-0.3	4743
0.3-0.4	2046
0.4-0.5	523
0.5-0.6	244
0.6-0.7	62
0.7-0.8	25
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8469	Intermediate Similarity	NPD6920	Discontinued
0.83	Intermediate Similarity	NPD6415	Discontinued
0.7857	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD8418	Phase 2
0.7326	Intermediate Similarity	NPD4244	Approved
0.7326	Intermediate Similarity	NPD4789	Approved
0.7326	Intermediate Similarity	NPD4245	Approved
0.7303	Intermediate Similarity	NPD6117	Approved
0.7294	Intermediate Similarity	NPD5360	Phase 3
0.7294	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD8298	Phase 2
0.7222	Intermediate Similarity	NPD6116	Phase 1
0.7209	Intermediate Similarity	NPD3698	Phase 2
0.7191	Intermediate Similarity	NPD3703	Phase 2
0.717	Intermediate Similarity	NPD7646	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6115	Approved
0.7143	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6118	Approved
0.7143	Intermediate Similarity	NPD6114	Approved
0.7143	Intermediate Similarity	NPD6697	Approved
0.6957	Remote Similarity	NPD3671	Phase 1
0.6916	Remote Similarity	NPD8040	Discontinued
0.6893	Remote Similarity	NPD7920	Phase 3
0.6893	Remote Similarity	NPD7919	Phase 3
0.6882	Remote Similarity	NPD7155	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4758	Discontinued
0.6827	Remote Similarity	NPD8088	Phase 1
0.6804	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7911	Approved
0.6729	Remote Similarity	NPD7912	Approved
0.6729	Remote Similarity	NPD7986	Approved
0.6729	Remote Similarity	NPD7987	Approved
0.6699	Remote Similarity	NPD7991	Discontinued
0.6667	Remote Similarity	NPD6081	Approved
0.6667	Remote Similarity	NPD4224	Phase 2
0.6667	Remote Similarity	NPD7754	Approved
0.6667	Remote Similarity	NPD7755	Approved
0.6638	Remote Similarity	NPD7519	Approved
0.6638	Remote Similarity	NPD7517	Approved
0.6638	Remote Similarity	NPD7518	Approved
0.6634	Remote Similarity	NPD6934	Discontinued
0.6606	Remote Similarity	NPD7333	Discontinued
0.6596	Remote Similarity	NPD5364	Discontinued
0.6566	Remote Similarity	NPD8308	Discontinued
0.6545	Remote Similarity	NPD7989	Approved
0.6545	Remote Similarity	NPD7990	Approved
0.6531	Remote Similarity	NPD4786	Approved
0.6484	Remote Similarity	NPD5777	Approved
0.6452	Remote Similarity	NPD3702	Approved
0.6444	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4788	Approved
0.6408	Remote Similarity	NPD8034	Phase 2
0.6408	Remote Similarity	NPD8035	Phase 2
0.6404	Remote Similarity	NPD8077	Approved
0.6404	Remote Similarity	NPD8078	Approved
0.64	Remote Similarity	NPD3618	Phase 1
0.6374	Remote Similarity	NPD4787	Phase 1
0.6373	Remote Similarity	NPD5328	Approved
0.6327	Remote Similarity	NPD3667	Approved
0.625	Remote Similarity	NPD6079	Approved
0.6239	Remote Similarity	NPD6940	Discontinued
0.6154	Remote Similarity	NPD6705	Phase 1
0.6154	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6700	Approved
0.6122	Remote Similarity	NPD6928	Phase 2
0.6116	Remote Similarity	NPD6909	Approved
0.6116	Remote Similarity	NPD6908	Approved
0.6111	Remote Similarity	NPD7751	Phase 1
0.6095	Remote Similarity	NPD6702	Approved
0.6095	Remote Similarity	NPD6703	Approved
0.6087	Remote Similarity	NPD3725	Approved
0.6087	Remote Similarity	NPD3726	Approved
0.6087	Remote Similarity	NPD2695	Approved
0.6087	Remote Similarity	NPD2697	Approved
0.6087	Remote Similarity	NPD2694	Approved
0.6087	Remote Similarity	NPD2696	Approved
0.6082	Remote Similarity	NPD4777	Suspended
0.6082	Remote Similarity	NPD4776	Phase 2
0.6071	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD3103	Approved
0.6055	Remote Similarity	NPD3101	Approved
0.6055	Remote Similarity	NPD3104	Approved
0.6055	Remote Similarity	NPD3102	Approved
0.604	Remote Similarity	NPD3666	Approved
0.604	Remote Similarity	NPD3665	Phase 1
0.604	Remote Similarity	NPD3133	Approved
0.6038	Remote Similarity	NPD4202	Approved
0.6038	Remote Similarity	NPD6399	Phase 3
0.6019	Remote Similarity	NPD4697	Phase 3
0.5943	Remote Similarity	NPD7515	Phase 2
0.5872	Remote Similarity	NPD5221	Approved
0.5872	Remote Similarity	NPD5222	Approved
0.5872	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD621	Discontinued
0.5854	Remote Similarity	NPD6921	Approved
0.5833	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD5173	Approved
0.5818	Remote Similarity	NPD4755	Approved
0.5816	Remote Similarity	NPD8143	Approved
0.5816	Remote Similarity	NPD8144	Approved
0.58	Remote Similarity	NPD7525	Registered
0.5776	Remote Similarity	NPD8174	Phase 2
0.5772	Remote Similarity	NPD7147	Phase 3
0.5772	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5279	Phase 3
0.5761	Remote Similarity	NPD375	Phase 2
0.576	Remote Similarity	NPD7122	Discontinued
0.5758	Remote Similarity	NPD3617	Approved
0.5755	Remote Similarity	NPD4753	Phase 2
0.5728	Remote Similarity	NPD3668	Phase 3
0.5714	Remote Similarity	NPD4700	Approved
0.5714	Remote Similarity	NPD5286	Approved
0.5714	Remote Similarity	NPD4696	Approved
0.5714	Remote Similarity	NPD5285	Approved
0.5688	Remote Similarity	NPD7748	Approved
0.5686	Remote Similarity	NPD4223	Phase 3
0.5686	Remote Similarity	NPD4221	Approved
0.5676	Remote Similarity	NPD7902	Approved
0.5673	Remote Similarity	NPD5329	Approved
0.5664	Remote Similarity	NPD5223	Approved
0.566	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD4629	Approved
0.5636	Remote Similarity	NPD5210	Approved
0.5619	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD3198	Approved
0.5614	Remote Similarity	NPD8138	Approved
0.5614	Remote Similarity	NPD5226	Approved
0.5614	Remote Similarity	NPD5211	Phase 2
0.5614	Remote Similarity	NPD8084	Approved
0.5614	Remote Similarity	NPD8083	Approved
0.5614	Remote Similarity	NPD8085	Approved
0.5614	Remote Similarity	NPD4633	Approved
0.5614	Remote Similarity	NPD8139	Approved
0.5614	Remote Similarity	NPD8082	Approved
0.5614	Remote Similarity	NPD5224	Approved
0.5614	Remote Similarity	NPD5225	Approved
0.5614	Remote Similarity	NPD8086	Approved
0.5612	Remote Similarity	NPD6942	Approved
0.5612	Remote Similarity	NPD7339	Approved
0.5603	Remote Similarity	NPD5739	Approved
0.5603	Remote Similarity	NPD6402	Approved
0.5603	Remote Similarity	NPD7128	Approved
0.5603	Remote Similarity	NPD6675	Approved
0.56	Remote Similarity	NPD617	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