NPASS Compound

Structure

CID174117 OpenBabel06191715542D 30 34 0 0 1 0 0 0 0 0999 V2000 6.5169 4.6198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6212 0.5742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4110 0.9586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8759 -0.5057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3404 2.9404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3797 2.9273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5351 3.4149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7673 2.1517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8446 -1.4630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6899 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5351 0.4883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6901 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9742 3.9330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9438 3.8311 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2247 1.4648 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6898 -0.9750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8452 1.4640 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3803 1.9523 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6904 1.9520 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8452 0.4880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8452 0.4880 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7977 2.2536 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8452 1.4639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5351 1.4643 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 4.4012 3.1442 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5559 -1.4750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7112 1.9639 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 8 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 8 24 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 27 1 0 0 0 0 12 26 1 0 0 0 0 13 18 1 0 0 0 0 13 23 1 0 0 0 0 14 25 1 0 0 0 0 15 16 1 0 0 0 0 15 28 1 0 0 0 0 16 1 1 1 0 0 0 17 2 1 1 0 0 0 17 20 1 0 0 0 0 18 29 1 6 0 0 0 19 14 1 1 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 20 26 1 6 0 0 0 21 26 1 6 0 0 0 22 27 1 6 0 0 0 23 25 1 0 0 0 0 23 27 1 6 0 0 0 24 17 1 6 0 0 0 24 28 1 0 0 0 0 25 30 2 0 0 0 0 26 3 1 6 0 0 0 27 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	415.35
Volume:	458.707
LogP:	4.616
LogD:	4.708
LogS:	-4.274
# Rotatable Bonds:	2
TPSA:	49.33
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.651
Synthetic Accessibility Score:	4.825
Fsp3:	0.963
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:	-4.855
MDCK Permeability:	9.041295015776996e-06
Pgp-inhibitor:	0.878
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.809
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.508
Plasma Protein Binding (PPB):	54.7105712890625%
Volume Distribution (VD):	1.046
Pgp-substrate:	14.137641906738281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.089
CYP1A2-substrate:	0.317
CYP2C19-inhibitor:	0.115
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.083
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.698
CYP3A4-inhibitor:	0.872
CYP3A4-substrate:	0.451

ADMET: Excretion

Clearance (CL):	18.902
Half-life (T1/2):	0.103

ADMET: Toxicity

hERG Blockers:	0.93
Human Hepatotoxicity (H-HT):	0.348
Drug-inuced Liver Injury (DILI):	0.341
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.699
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.946
Carcinogencity:	0.32
Eye Corrosion:	0.334
Eye Irritation:	0.013
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC174117

Natural Product ID:	NPC174117
*Common Name:**	(22R,25S)-22,26-Epiminocholest-3Beta-Ol-6-One
IUPAC Name:	(3S,5S,8S,9S,10R,13S,14S,17R)-3-hydroxy-10,13-dimethyl-17-[(1S)-1-[(2R,5S)-5-methylpiperidin-2-yl]ethyl]-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
Synonyms:	N-demethylpuqietinone
Standard InCHIKey:	UUCQCKZTFQEWEI-IVJVQQFWSA-N
Standard InCHI:	InChI=1S/C27H45NO2/c1-16-5-8-24(28-15-16)17(2)20-6-7-21-19-14-25(30)23-13-18(29)9-11-27(23,4)22(19)10-12-26(20,21)3/h16-24,28-29H,5-15H2,1-4H3/t16-,17-,18-,19-,20+,21-,22-,23+,24+,26+,27+/m0/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)NC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498462
PubChem CID:	11304576
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]
NPO20194	Fritillaria puqiensis	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]
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]
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]
NPO5648	Fritillaria ussuriensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22292	Fritillaria przewalskii	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]
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[TCMID]
NPO5648	Fritillaria ussuriensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22292	Fritillaria przewalskii	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]
NPO5648	Fritillaria ussuriensis	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]
NPO1279	Fritillaria cirrhosa	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[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]
NPO14849	Fritillaria unibracteata	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]
NPO5648	Fritillaria ussuriensis	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]
NPO5648	Fritillaria ussuriensis	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]
NPO11228	Fritillaria pallidiflora	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	3

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	51.0	%	PMID[460788]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	18.0	n.a.	PMID[460788]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	23.0	n.a.	PMID[460788]

☑ 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 NPC174117 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	130
0.1-0.2	1975
0.2-0.3	17507
0.3-0.4	11539
0.4-0.5	6326
0.5-0.6	4327
0.6-0.7	789
0.7-0.8	99
0.8-0.85	1
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9326	High Similarity	NPC312637
0.8646	High Similarity	NPC220111
0.8077	Intermediate Similarity	NPC473994
0.8039	Intermediate Similarity	NPC475239
0.7959	Intermediate Similarity	NPC155985
0.785	Intermediate Similarity	NPC124358
0.7812	Intermediate Similarity	NPC135005
0.7714	Intermediate Similarity	NPC476756
0.7714	Intermediate Similarity	NPC244982
0.7615	Intermediate Similarity	NPC28224
0.7568	Intermediate Similarity	NPC39485
0.7568	Intermediate Similarity	NPC221196
0.7527	Intermediate Similarity	NPC109533
0.75	Intermediate Similarity	NPC151018
0.75	Intermediate Similarity	NPC320549
0.75	Intermediate Similarity	NPC156277
0.75	Intermediate Similarity	NPC58057
0.7473	Intermediate Similarity	NPC23884
0.7451	Intermediate Similarity	NPC473537
0.7451	Intermediate Similarity	NPC474164
0.7444	Intermediate Similarity	NPC174964
0.7444	Intermediate Similarity	NPC195155
0.7444	Intermediate Similarity	NPC97534
0.7434	Intermediate Similarity	NPC475340
0.7423	Intermediate Similarity	NPC21035
0.7416	Intermediate Similarity	NPC232112
0.7379	Intermediate Similarity	NPC475249
0.7379	Intermediate Similarity	NPC252564
0.7363	Intermediate Similarity	NPC475742
0.7363	Intermediate Similarity	NPC472486
0.7363	Intermediate Similarity	NPC5767
0.7363	Intermediate Similarity	NPC472487
0.7333	Intermediate Similarity	NPC254340
0.7333	Intermediate Similarity	NPC470592
0.7333	Intermediate Similarity	NPC176012
0.7308	Intermediate Similarity	NPC201712
0.7303	Intermediate Similarity	NPC89310
0.7283	Intermediate Similarity	NPC221420
0.7273	Intermediate Similarity	NPC34977
0.7273	Intermediate Similarity	NPC131892
0.7273	Intermediate Similarity	NPC213178
0.7273	Intermediate Similarity	NPC327728
0.7273	Intermediate Similarity	NPC6120
0.7273	Intermediate Similarity	NPC246399
0.7264	Intermediate Similarity	NPC98765
0.7253	Intermediate Similarity	NPC273366
0.7253	Intermediate Similarity	NPC125767
0.7253	Intermediate Similarity	NPC21220
0.725	Intermediate Similarity	NPC478139
0.7238	Intermediate Similarity	NPC475518
0.717	Intermediate Similarity	NPC476755
0.7143	Intermediate Similarity	NPC280026
0.7143	Intermediate Similarity	NPC167702
0.7115	Intermediate Similarity	NPC292819
0.7111	Intermediate Similarity	NPC110615
0.7097	Intermediate Similarity	NPC143133
0.7097	Intermediate Similarity	NPC475031
0.7097	Intermediate Similarity	NPC298168
0.7065	Intermediate Similarity	NPC212733
0.7053	Intermediate Similarity	NPC470609
0.7033	Intermediate Similarity	NPC310766
0.7021	Intermediate Similarity	NPC185465
0.7019	Intermediate Similarity	NPC289140
0.7018	Intermediate Similarity	NPC476955
0.7	Intermediate Similarity	NPC317654
0.7	Intermediate Similarity	NPC96010
0.6989	Remote Similarity	NPC4209
0.6979	Remote Similarity	NPC192456
0.6972	Remote Similarity	NPC195841
0.6972	Remote Similarity	NPC233256
0.6957	Remote Similarity	NPC168511
0.6957	Remote Similarity	NPC159325
0.6957	Remote Similarity	NPC133922
0.6947	Remote Similarity	NPC320144
0.6939	Remote Similarity	NPC474482
0.6939	Remote Similarity	NPC475745
0.6915	Remote Similarity	NPC207010
0.6915	Remote Similarity	NPC317913
0.6907	Remote Similarity	NPC61107
0.6907	Remote Similarity	NPC289486
0.6907	Remote Similarity	NPC317066
0.6907	Remote Similarity	NPC30583
0.6907	Remote Similarity	NPC328007
0.6889	Remote Similarity	NPC324607
0.6889	Remote Similarity	NPC321732
0.6882	Remote Similarity	NPC477002
0.6882	Remote Similarity	NPC159789
0.6848	Remote Similarity	NPC477229
0.6848	Remote Similarity	NPC282905
0.6848	Remote Similarity	NPC68426
0.6842	Remote Similarity	NPC34046
0.6842	Remote Similarity	NPC171426
0.6842	Remote Similarity	NPC224802
0.6842	Remote Similarity	NPC80089
0.6842	Remote Similarity	NPC324700
0.6838	Remote Similarity	NPC35037
0.6837	Remote Similarity	NPC472743
0.6837	Remote Similarity	NPC475726
0.6813	Remote Similarity	NPC306973
0.6809	Remote Similarity	NPC108840
0.6804	Remote Similarity	NPC58631
0.6804	Remote Similarity	NPC469745
0.68	Remote Similarity	NPC472738
0.6786	Remote Similarity	NPC85001
0.6786	Remote Similarity	NPC95920
0.6786	Remote Similarity	NPC253645
0.6786	Remote Similarity	NPC147835
0.6778	Remote Similarity	NPC473225
0.6774	Remote Similarity	NPC130011
0.6774	Remote Similarity	NPC472854
0.6771	Remote Similarity	NPC80891
0.6771	Remote Similarity	NPC201276
0.6768	Remote Similarity	NPC474996
0.6768	Remote Similarity	NPC474233
0.6739	Remote Similarity	NPC473267
0.6737	Remote Similarity	NPC264602
0.6735	Remote Similarity	NPC268040
0.6723	Remote Similarity	NPC238323
0.6703	Remote Similarity	NPC469941
0.6703	Remote Similarity	NPC319671
0.6703	Remote Similarity	NPC476734
0.6703	Remote Similarity	NPC252032
0.6702	Remote Similarity	NPC267753
0.6701	Remote Similarity	NPC261616
0.67	Remote Similarity	NPC292553
0.6667	Remote Similarity	NPC472744
0.6667	Remote Similarity	NPC329117
0.6667	Remote Similarity	NPC323180
0.6667	Remote Similarity	NPC472739
0.6667	Remote Similarity	NPC81759
0.6667	Remote Similarity	NPC474719
0.6667	Remote Similarity	NPC327451
0.6638	Remote Similarity	NPC135431
0.6633	Remote Similarity	NPC12933
0.6633	Remote Similarity	NPC50658
0.663	Remote Similarity	NPC477929
0.663	Remote Similarity	NPC476731
0.663	Remote Similarity	NPC108131
0.6607	Remote Similarity	NPC83047
0.6607	Remote Similarity	NPC267217
0.6607	Remote Similarity	NPC8009
0.6607	Remote Similarity	NPC48127
0.66	Remote Similarity	NPC473336
0.66	Remote Similarity	NPC264665
0.66	Remote Similarity	NPC50438
0.66	Remote Similarity	NPC74595
0.66	Remote Similarity	NPC471044
0.66	Remote Similarity	NPC175419
0.6598	Remote Similarity	NPC201459
0.6593	Remote Similarity	NPC2568
0.6593	Remote Similarity	NPC260319
0.6593	Remote Similarity	NPC474954
0.6593	Remote Similarity	NPC103647
0.6593	Remote Similarity	NPC180777
0.6591	Remote Similarity	NPC114891
0.6581	Remote Similarity	NPC209252
0.6577	Remote Similarity	NPC470596
0.6574	Remote Similarity	NPC91604
0.6571	Remote Similarity	NPC161035
0.6569	Remote Similarity	NPC4643
0.6569	Remote Similarity	NPC57469
0.6566	Remote Similarity	NPC121121
0.6559	Remote Similarity	NPC126642
0.6556	Remote Similarity	NPC142712
0.6535	Remote Similarity	NPC294438
0.6535	Remote Similarity	NPC264317
0.6535	Remote Similarity	NPC76518
0.6531	Remote Similarity	NPC164999
0.6531	Remote Similarity	NPC477851
0.6526	Remote Similarity	NPC24014
0.6526	Remote Similarity	NPC27349
0.6526	Remote Similarity	NPC472311
0.6522	Remote Similarity	NPC66862
0.6514	Remote Similarity	NPC135799
0.6514	Remote Similarity	NPC239768
0.6514	Remote Similarity	NPC128698
0.6505	Remote Similarity	NPC90676
0.6495	Remote Similarity	NPC472608
0.6495	Remote Similarity	NPC26029
0.6484	Remote Similarity	NPC48079
0.6484	Remote Similarity	NPC472984
0.6477	Remote Similarity	NPC148174
0.6477	Remote Similarity	NPC71460
0.6477	Remote Similarity	NPC218585
0.6471	Remote Similarity	NPC476726
0.6471	Remote Similarity	NPC269396
0.6471	Remote Similarity	NPC119633
0.6471	Remote Similarity	NPC321340
0.6471	Remote Similarity	NPC270957
0.6471	Remote Similarity	NPC171698
0.6471	Remote Similarity	NPC80700
0.6471	Remote Similarity	NPC2783
0.6471	Remote Similarity	NPC12774
0.6471	Remote Similarity	NPC476727
0.6471	Remote Similarity	NPC98236
0.6465	Remote Similarity	NPC474484
0.6465	Remote Similarity	NPC280781
0.6465	Remote Similarity	NPC103754
0.6465	Remote Similarity	NPC48756
0.646	Remote Similarity	NPC46981

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 NPC174117 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	84
0.1-0.2	1263
0.2-0.3	4753
0.3-0.4	2200
0.4-0.5	562
0.5-0.6	212
0.6-0.7	55
0.7-0.8	20
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7961	Intermediate Similarity	NPD6920	Discontinued
0.781	Intermediate Similarity	NPD6415	Discontinued
0.75	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7919	Phase 3
0.7451	Intermediate Similarity	NPD7920	Phase 3
0.7379	Intermediate Similarity	NPD8088	Phase 1
0.7273	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8308	Discontinued
0.7143	Intermediate Similarity	NPD8418	Phase 2
0.7143	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4245	Approved
0.7	Intermediate Similarity	NPD4244	Approved
0.7	Intermediate Similarity	NPD4789	Approved
0.6989	Remote Similarity	NPD6117	Approved
0.6966	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5360	Phase 3
0.6915	Remote Similarity	NPD6116	Phase 1
0.6889	Remote Similarity	NPD3698	Phase 2
0.6882	Remote Similarity	NPD3703	Phase 2
0.6842	Remote Similarity	NPD6114	Approved
0.6842	Remote Similarity	NPD6697	Approved
0.6842	Remote Similarity	NPD6115	Approved
0.6842	Remote Similarity	NPD6118	Approved
0.6842	Remote Similarity	NPD8298	Phase 2
0.6818	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3671	Phase 1
0.6559	Remote Similarity	NPD4758	Discontinued
0.6535	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD8040	Discontinued
0.6495	Remote Similarity	NPD4777	Suspended
0.6495	Remote Similarity	NPD4776	Phase 2
0.6441	Remote Similarity	NPD6940	Discontinued
0.6429	Remote Similarity	NPD7155	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD621	Discontinued
0.6389	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6081	Approved
0.6374	Remote Similarity	NPD4224	Phase 2
0.6339	Remote Similarity	NPD7912	Approved
0.6339	Remote Similarity	NPD7986	Approved
0.6339	Remote Similarity	NPD7911	Approved
0.6339	Remote Similarity	NPD7987	Approved
0.6327	Remote Similarity	NPD5364	Discontinued
0.6303	Remote Similarity	NPD7754	Approved
0.6303	Remote Similarity	NPD7755	Approved
0.6299	Remote Similarity	NPD7751	Phase 1
0.6296	Remote Similarity	NPD7991	Discontinued
0.6281	Remote Similarity	NPD7518	Approved
0.6281	Remote Similarity	NPD7517	Approved
0.6281	Remote Similarity	NPD7519	Approved
0.6275	Remote Similarity	NPD4786	Approved
0.6228	Remote Similarity	NPD7333	Discontinued
0.6226	Remote Similarity	NPD6934	Discontinued
0.6211	Remote Similarity	NPD5777	Approved
0.6186	Remote Similarity	NPD3702	Approved
0.6176	Remote Similarity	NPD4788	Approved
0.6174	Remote Similarity	NPD7989	Approved
0.6174	Remote Similarity	NPD7990	Approved
0.617	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD8034	Phase 2
0.6168	Remote Similarity	NPD8035	Phase 2
0.6162	Remote Similarity	NPD617	Approved
0.6154	Remote Similarity	NPD3618	Phase 1
0.6132	Remote Similarity	NPD5328	Approved
0.6126	Remote Similarity	NPD3101	Approved
0.6126	Remote Similarity	NPD3104	Approved
0.6126	Remote Similarity	NPD3103	Approved
0.6126	Remote Similarity	NPD3102	Approved
0.6105	Remote Similarity	NPD4787	Phase 1
0.6098	Remote Similarity	NPD7147	Phase 3
0.6098	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD3667	Approved
0.605	Remote Similarity	NPD8078	Approved
0.605	Remote Similarity	NPD8077	Approved
0.6022	Remote Similarity	NPD375	Phase 2
0.6019	Remote Similarity	NPD6079	Approved
0.5926	Remote Similarity	NPD6700	Approved
0.5926	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7336	Phase 2
0.5917	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7335	Phase 2
0.5895	Remote Similarity	NPD6705	Phase 1
0.5882	Remote Similarity	NPD6928	Phase 2
0.5872	Remote Similarity	NPD6702	Approved
0.5872	Remote Similarity	NPD6703	Approved
0.5872	Remote Similarity	NPD6699	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD6399	Phase 3
0.5818	Remote Similarity	NPD4202	Approved
0.581	Remote Similarity	NPD3665	Phase 1
0.581	Remote Similarity	NPD3666	Approved
0.581	Remote Similarity	NPD3133	Approved
0.5804	Remote Similarity	NPD4697	Phase 3
0.5794	Remote Similarity	NPD6908	Approved
0.5794	Remote Similarity	NPD6909	Approved
0.5763	Remote Similarity	NPD8175	Discontinued
0.5727	Remote Similarity	NPD7515	Phase 2
0.5714	Remote Similarity	NPD8449	Approved
0.5672	Remote Similarity	NPD8450	Suspended
0.567	Remote Similarity	NPD2694	Approved
0.567	Remote Similarity	NPD2697	Approved
0.567	Remote Similarity	NPD2696	Approved
0.567	Remote Similarity	NPD2695	Approved
0.567	Remote Similarity	NPD3725	Approved
0.567	Remote Similarity	NPD3726	Approved
0.5664	Remote Similarity	NPD5222	Approved
0.5664	Remote Similarity	NPD5221	Approved
0.5664	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.563	Remote Similarity	NPD1126	Phase 2
0.5625	Remote Similarity	NPD2636	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD2637	Approved
0.5614	Remote Similarity	NPD5173	Approved
0.5614	Remote Similarity	NPD4755	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