NPASS Compound

Structure

CID189863 OpenBabel06191715572D 28 32 0 0 1 0 0 0 0 0999 V2000 -1.6565 -1.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8744 -0.5049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1734 -0.8424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3747 -0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5309 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1467 -0.8424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3741 -2.9224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5306 -2.4357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2182 -1.4614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1734 0.8434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6867 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3747 -0.9747 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2179 -2.4352 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6871 -0.0003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6871 -0.9747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8438 0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6334 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8433 0.4869 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5309 -1.4619 0.0000 C 0 0 2 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 -5.0839 -2.9353 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2589 2.9133 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6067 0.0005 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1467 0.8434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 6 2 0 0 0 0 3 14 1 0 0 0 0 4 5 1 0 0 0 0 4 15 1 0 0 0 0 6 21 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 19 1 0 0 0 0 12 20 1 0 0 0 0 13 14 2 0 0 0 0 13 28 1 0 0 0 0 14 19 1 0 0 0 0 15 23 1 1 0 0 0 16 25 1 6 0 0 0 17 5 1 1 0 0 0 17 18 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 6 0 0 0 19 24 1 6 0 0 0 20 22 1 0 0 0 0 20 26 2 0 0 0 0 21 27 2 0 0 0 0 21 28 1 0 0 0 0 22 24 1 6 0 0 0 23 1 1 6 0 0 0 24 2 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.23
Volume:	405.493
LogP:	3.99
LogD:	4.049
LogS:	-4.51
# Rotatable Bonds:	1
TPSA:	67.51
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.784
Synthetic Accessibility Score:	4.439
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.707
MDCK Permeability:	3.023113458766602e-05
Pgp-inhibitor:	0.885
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.368
Plasma Protein Binding (PPB):	89.73778533935547%
Volume Distribution (VD):	0.801
Pgp-substrate:	6.874425888061523%

ADMET: Metabolism

CYP1A2-inhibitor:	0.152
CYP1A2-substrate:	0.572
CYP2C19-inhibitor:	0.222
CYP2C19-substrate:	0.526
CYP2C9-inhibitor:	0.276
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.235
CYP3A4-inhibitor:	0.831
CYP3A4-substrate:	0.256

ADMET: Excretion

Clearance (CL):	15.995
Half-life (T1/2):	0.331

ADMET: Toxicity

hERG Blockers:	0.421
Human Hepatotoxicity (H-HT):	0.325
Drug-inuced Liver Injury (DILI):	0.196
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.962
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.679
Carcinogencity:	0.715
Eye Corrosion:	0.369
Eye Irritation:	0.076
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC189863

Natural Product ID:	NPC189863
*Common Name:**	5-(3-Hydroxy-10,13-Dimethyl-15-Oxo-Hexadecahydro-Cyclopenta[A]Phenanthren-17-Yl)-Pyran-2-One
IUPAC Name:	5-[(3S,5R,8R,9S,10S,13R,14S,17S)-3-hydroxy-10,13-dimethyl-15-oxo-1,2,3,4,5,6,7,8,9,11,12,14,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
Synonyms:
Standard InCHIKey:	NTLOERPHSXBROY-YUHXZNIQSA-N
Standard InCHI:	InChI=1S/C24H32O4/c1-23-9-7-16(25)11-15(23)4-5-17-18(23)8-10-24(2)19(12-20(26)22(17)24)14-3-6-21(27)28-13-14/h3,6,13,15-19,22,25H,4-5,7-12H2,1-2H3/t15-,16+,17-,18+,19-,22-,23+,24-/m1/s1
SMILES:	O[C@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1C(=O)C[C@@H]2c1ccc(=O)oc1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3138316
PubChem CID:	12308599
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001557] Bufanolides and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)99818-1]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	roots	n.a.	n.a.	PMID[10346940]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421725]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165135]
NPO3983	Piper futokadsura	Species	Piperaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[15635246]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730237]
NPO664	Potentilla multifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17504571]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21185919]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[21954912]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	twigs and leaves	Yunnan Province, China	2008-OCT	PMID[21954912]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21954912]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22708620]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26722868]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223924]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11515	Streptomyces plumbeus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26231	Vicia villosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2917	Artemisia oranensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7543	Haplopappus venetus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12250	Strychnos fendleri	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3983	Piper futokadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4797	Gavia immer	Species	Gaviidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12952	Cabucala madagascariensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10043	Phebalium ozothamnoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5177	Lecanora conizaeoides	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6887	Lytanthus salicinus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12735	Halimeda macroloba	Species	Halimedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9398	Cortinarius rubellus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2498	Kochia trichophylla	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6011	Pleurotus citrinopileatus	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21463	Aruncus dioicus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO664	Potentilla multifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7884	Centaurea amara	Species	Asteraceae	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	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	8.2	ug.mL-1	PMID[557474]
NPT2	Others	Unspecified		IC50	=	12.0	ug.mL-1	PMID[557474]

☑ 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 NPC189863 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	322
0.1-0.2	1410
0.2-0.3	2557
0.3-0.4	5375
0.4-0.5	11252
0.5-0.6	9969
0.6-0.7	9996
0.7-0.8	1574
0.8-0.85	172
0.85-0.9	44
0.9-0.95	25
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.94	High Similarity	NPC266570
0.9223	High Similarity	NPC16270
0.9184	High Similarity	NPC108368
0.9184	High Similarity	NPC57079
0.9143	High Similarity	NPC73050
0.901	High Similarity	NPC171014
0.9	High Similarity	NPC194028
0.9	High Similarity	NPC168319
0.8981	High Similarity	NPC146786
0.8952	High Similarity	NPC474315
0.8835	High Similarity	NPC295843
0.8788	High Similarity	NPC250757
0.8788	High Similarity	NPC301534
0.875	High Similarity	NPC43063
0.875	High Similarity	NPC79298
0.8725	High Similarity	NPC155332
0.8725	High Similarity	NPC114540
0.8725	High Similarity	NPC32577
0.8713	High Similarity	NPC201406
0.87	High Similarity	NPC253826
0.8667	High Similarity	NPC137462
0.8667	High Similarity	NPC275060
0.8667	High Similarity	NPC304276
0.8649	High Similarity	NPC114939
0.8649	High Similarity	NPC41123
0.8649	High Similarity	NPC145074
0.8649	High Similarity	NPC184555
0.8641	High Similarity	NPC112009
0.8614	High Similarity	NPC98868
0.8585	High Similarity	NPC75389
0.8529	High Similarity	NPC266955
0.8505	High Similarity	NPC103491
0.8505	High Similarity	NPC12795
0.85	High Similarity	NPC139459
0.85	High Similarity	NPC476174
0.8491	Intermediate Similarity	NPC220155
0.8462	Intermediate Similarity	NPC180204
0.8447	Intermediate Similarity	NPC115899
0.8447	Intermediate Similarity	NPC282524
0.844	Intermediate Similarity	NPC122056
0.8426	Intermediate Similarity	NPC183603
0.8421	Intermediate Similarity	NPC55602
0.8416	Intermediate Similarity	NPC471153
0.84	Intermediate Similarity	NPC299100
0.8396	Intermediate Similarity	NPC475294
0.8396	Intermediate Similarity	NPC329048
0.8396	Intermediate Similarity	NPC330011
0.8396	Intermediate Similarity	NPC91034
0.8384	Intermediate Similarity	NPC473986
0.8384	Intermediate Similarity	NPC474018
0.8384	Intermediate Similarity	NPC272746
0.8381	Intermediate Similarity	NPC472868
0.8364	Intermediate Similarity	NPC67259
0.8364	Intermediate Similarity	NPC147912
0.8349	Intermediate Similarity	NPC44537
0.8333	Intermediate Similarity	NPC110937
0.8333	Intermediate Similarity	NPC2049
0.8333	Intermediate Similarity	NPC202705
0.8333	Intermediate Similarity	NPC108078
0.8317	Intermediate Similarity	NPC171395
0.8317	Intermediate Similarity	NPC180950
0.8317	Intermediate Similarity	NPC33473
0.8317	Intermediate Similarity	NPC88310
0.8302	Intermediate Similarity	NPC478052
0.8286	Intermediate Similarity	NPC72151
0.8286	Intermediate Similarity	NPC329345
0.8286	Intermediate Similarity	NPC473283
0.8286	Intermediate Similarity	NPC475526
0.8283	Intermediate Similarity	NPC474842
0.8283	Intermediate Similarity	NPC475965
0.8273	Intermediate Similarity	NPC241977
0.8273	Intermediate Similarity	NPC154815
0.8273	Intermediate Similarity	NPC171126
0.8269	Intermediate Similarity	NPC310981
0.8269	Intermediate Similarity	NPC476223
0.8269	Intermediate Similarity	NPC476240
0.8269	Intermediate Similarity	NPC224720
0.8261	Intermediate Similarity	NPC6193
0.8252	Intermediate Similarity	NPC166745
0.8252	Intermediate Similarity	NPC235464
0.8252	Intermediate Similarity	NPC103051
0.8252	Intermediate Similarity	NPC92275
0.8241	Intermediate Similarity	NPC475065
0.8241	Intermediate Similarity	NPC228477
0.8241	Intermediate Similarity	NPC137911
0.8235	Intermediate Similarity	NPC29152
0.8235	Intermediate Similarity	NPC190713
0.8235	Intermediate Similarity	NPC16967
0.822	Intermediate Similarity	NPC221414
0.8218	Intermediate Similarity	NPC474690
0.8218	Intermediate Similarity	NPC91010
0.8218	Intermediate Similarity	NPC469406
0.8218	Intermediate Similarity	NPC191521
0.8218	Intermediate Similarity	NPC8993
0.8214	Intermediate Similarity	NPC286528
0.8214	Intermediate Similarity	NPC20302
0.8214	Intermediate Similarity	NPC167606
0.8214	Intermediate Similarity	NPC140055
0.8208	Intermediate Similarity	NPC165969
0.82	Intermediate Similarity	NPC475806
0.82	Intermediate Similarity	NPC473998
0.819	Intermediate Similarity	NPC233041
0.819	Intermediate Similarity	NPC320447
0.8182	Intermediate Similarity	NPC69291
0.8182	Intermediate Similarity	NPC309603
0.8182	Intermediate Similarity	NPC474844
0.8182	Intermediate Similarity	NPC473999
0.8182	Intermediate Similarity	NPC247760
0.8173	Intermediate Similarity	NPC476274
0.8173	Intermediate Similarity	NPC117685
0.8173	Intermediate Similarity	NPC35751
0.8173	Intermediate Similarity	NPC251680
0.8165	Intermediate Similarity	NPC37116
0.8163	Intermediate Similarity	NPC163016
0.8163	Intermediate Similarity	NPC93778
0.8163	Intermediate Similarity	NPC75315
0.8163	Intermediate Similarity	NPC477228
0.8163	Intermediate Similarity	NPC141292
0.8158	Intermediate Similarity	NPC476962
0.8155	Intermediate Similarity	NPC156546
0.8148	Intermediate Similarity	NPC475418
0.8148	Intermediate Similarity	NPC318363
0.8148	Intermediate Similarity	NPC473482
0.8148	Intermediate Similarity	NPC472825
0.8142	Intermediate Similarity	NPC50774
0.8142	Intermediate Similarity	NPC709
0.8137	Intermediate Similarity	NPC293052
0.8137	Intermediate Similarity	NPC209355
0.8131	Intermediate Similarity	NPC34768
0.812	Intermediate Similarity	NPC159499
0.8119	Intermediate Similarity	NPC472871
0.8119	Intermediate Similarity	NPC295643
0.8119	Intermediate Similarity	NPC214697
0.8119	Intermediate Similarity	NPC272075
0.8119	Intermediate Similarity	NPC139692
0.8119	Intermediate Similarity	NPC476304
0.8119	Intermediate Similarity	NPC214756
0.8113	Intermediate Similarity	NPC297617
0.8113	Intermediate Similarity	NPC476237
0.8113	Intermediate Similarity	NPC476889
0.8113	Intermediate Similarity	NPC475050
0.81	Intermediate Similarity	NPC273199
0.81	Intermediate Similarity	NPC85173
0.81	Intermediate Similarity	NPC198818
0.81	Intermediate Similarity	NPC126993
0.8095	Intermediate Similarity	NPC99411
0.8095	Intermediate Similarity	NPC118174
0.8081	Intermediate Similarity	NPC292491
0.8081	Intermediate Similarity	NPC310752
0.8077	Intermediate Similarity	NPC218107
0.8077	Intermediate Similarity	NPC478056
0.8077	Intermediate Similarity	NPC114274
0.807	Intermediate Similarity	NPC264954
0.8058	Intermediate Similarity	NPC160056
0.8058	Intermediate Similarity	NPC472941
0.8058	Intermediate Similarity	NPC456
0.8058	Intermediate Similarity	NPC78473
0.8056	Intermediate Similarity	NPC473284
0.8056	Intermediate Similarity	NPC179380
0.8053	Intermediate Similarity	NPC185287
0.8053	Intermediate Similarity	NPC157380
0.8053	Intermediate Similarity	NPC470492
0.8053	Intermediate Similarity	NPC470493
0.8053	Intermediate Similarity	NPC183580
0.8053	Intermediate Similarity	NPC312824
0.8053	Intermediate Similarity	NPC243065
0.8039	Intermediate Similarity	NPC476186
0.8039	Intermediate Similarity	NPC49670
0.8039	Intermediate Similarity	NPC201725
0.802	Intermediate Similarity	NPC65120
0.802	Intermediate Similarity	NPC212948
0.802	Intermediate Similarity	NPC158030
0.802	Intermediate Similarity	NPC204341
0.802	Intermediate Similarity	NPC233455
0.802	Intermediate Similarity	NPC4036
0.802	Intermediate Similarity	NPC110923
0.802	Intermediate Similarity	NPC145067
0.802	Intermediate Similarity	NPC74296
0.8019	Intermediate Similarity	NPC31058
0.8019	Intermediate Similarity	NPC476890
0.8019	Intermediate Similarity	NPC469606
0.8019	Intermediate Similarity	NPC136289
0.8019	Intermediate Similarity	NPC40918
0.8019	Intermediate Similarity	NPC293753
0.8019	Intermediate Similarity	NPC273005
0.8018	Intermediate Similarity	NPC191620
0.8018	Intermediate Similarity	NPC475524
0.8018	Intermediate Similarity	NPC100267
0.8018	Intermediate Similarity	NPC236217
0.8	Intermediate Similarity	NPC474704
0.8	Intermediate Similarity	NPC84271
0.8	Intermediate Similarity	NPC102414
0.8	Intermediate Similarity	NPC66344
0.8	Intermediate Similarity	NPC179642
0.8	Intermediate Similarity	NPC473627
0.8	Intermediate Similarity	NPC29133
0.8	Intermediate Similarity	NPC477720
0.8	Intermediate Similarity	NPC177141
0.8	Intermediate Similarity	NPC474370
0.8	Intermediate Similarity	NPC474012

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 NPC189863 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	296
0.1-0.2	872
0.2-0.3	1391
0.3-0.4	2492
0.4-0.5	2375
0.5-0.6	1287
0.6-0.7	390
0.7-0.8	45
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8252	Intermediate Similarity	NPD7638	Approved
0.8214	Intermediate Similarity	NPD7115	Discovery
0.8173	Intermediate Similarity	NPD7640	Approved
0.8173	Intermediate Similarity	NPD7639	Approved
0.802	Intermediate Similarity	NPD6079	Approved
0.802	Intermediate Similarity	NPD7515	Phase 2
0.7864	Intermediate Similarity	NPD7748	Approved
0.7822	Intermediate Similarity	NPD5328	Approved
0.7818	Intermediate Similarity	NPD6899	Approved
0.7818	Intermediate Similarity	NPD6881	Approved
0.7778	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD6399	Phase 3
0.7727	Intermediate Similarity	NPD5697	Approved
0.7723	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD5222	Approved
0.7714	Intermediate Similarity	NPD5221	Approved
0.7714	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD3618	Phase 1
0.7679	Intermediate Similarity	NPD7102	Approved
0.7679	Intermediate Similarity	NPD6883	Approved
0.7679	Intermediate Similarity	NPD7290	Approved
0.7677	Intermediate Similarity	NPD4786	Approved
0.7658	Intermediate Similarity	NPD6011	Approved
0.7642	Intermediate Similarity	NPD7902	Approved
0.7642	Intermediate Similarity	NPD6083	Phase 2
0.7642	Intermediate Similarity	NPD5173	Approved
0.7642	Intermediate Similarity	NPD6084	Phase 2
0.7636	Intermediate Similarity	NPD6402	Approved
0.7636	Intermediate Similarity	NPD5739	Approved
0.7636	Intermediate Similarity	NPD7128	Approved
0.7636	Intermediate Similarity	NPD6675	Approved
0.7611	Intermediate Similarity	NPD6869	Approved
0.7611	Intermediate Similarity	NPD6649	Approved
0.7611	Intermediate Similarity	NPD6847	Approved
0.7611	Intermediate Similarity	NPD8130	Phase 1
0.7611	Intermediate Similarity	NPD6617	Approved
0.7611	Intermediate Similarity	NPD6650	Approved
0.7589	Intermediate Similarity	NPD6012	Approved
0.7589	Intermediate Similarity	NPD6013	Approved
0.7589	Intermediate Similarity	NPD6014	Approved
0.7549	Intermediate Similarity	NPD5737	Approved
0.7549	Intermediate Similarity	NPD6672	Approved
0.7544	Intermediate Similarity	NPD8297	Approved
0.7544	Intermediate Similarity	NPD6882	Approved
0.7525	Intermediate Similarity	NPD6684	Approved
0.7525	Intermediate Similarity	NPD7334	Approved
0.7525	Intermediate Similarity	NPD5330	Approved
0.7525	Intermediate Similarity	NPD7521	Approved
0.7525	Intermediate Similarity	NPD6409	Approved
0.7525	Intermediate Similarity	NPD7146	Approved
0.7525	Intermediate Similarity	NPD5279	Phase 3
0.7523	Intermediate Similarity	NPD5211	Phase 2
0.7523	Intermediate Similarity	NPD7632	Discontinued
0.75	Intermediate Similarity	NPD5286	Approved
0.75	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD5281	Approved
0.75	Intermediate Similarity	NPD8035	Phase 2
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD8034	Phase 2
0.75	Intermediate Similarity	NPD3666	Approved
0.75	Intermediate Similarity	NPD4696	Approved
0.75	Intermediate Similarity	NPD5285	Approved
0.75	Intermediate Similarity	NPD5284	Approved
0.7479	Intermediate Similarity	NPD7503	Approved
0.7476	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD3667	Approved
0.7475	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6373	Approved
0.7434	Intermediate Similarity	NPD6372	Approved
0.7431	Intermediate Similarity	NPD5223	Approved
0.7429	Intermediate Similarity	NPD4202	Approved
0.7411	Intermediate Similarity	NPD5701	Approved
0.7404	Intermediate Similarity	NPD5785	Approved
0.74	Intermediate Similarity	NPD4788	Approved
0.7387	Intermediate Similarity	NPD5141	Approved
0.7383	Intermediate Similarity	NPD4697	Phase 3
0.7379	Intermediate Similarity	NPD6903	Approved
0.7364	Intermediate Similarity	NPD5224	Approved
0.7364	Intermediate Similarity	NPD5225	Approved
0.7364	Intermediate Similarity	NPD4633	Approved
0.7364	Intermediate Similarity	NPD5226	Approved
0.7358	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7900	Approved
0.735	Intermediate Similarity	NPD6868	Approved
0.7333	Intermediate Similarity	NPD5693	Phase 1
0.7328	Intermediate Similarity	NPD4632	Approved
0.7315	Intermediate Similarity	NPD4755	Approved
0.7308	Intermediate Similarity	NPD4753	Phase 2
0.7304	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5175	Approved
0.7297	Intermediate Similarity	NPD5174	Approved
0.729	Intermediate Similarity	NPD4629	Approved
0.729	Intermediate Similarity	NPD5210	Approved
0.729	Intermediate Similarity	NPD5695	Phase 3
0.7255	Intermediate Similarity	NPD1694	Approved
0.7248	Intermediate Similarity	NPD5696	Approved
0.7248	Intermediate Similarity	NPD4225	Approved
0.7245	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6053	Discontinued
0.7236	Intermediate Similarity	NPD7507	Approved
0.7227	Intermediate Similarity	NPD6335	Approved
0.7193	Intermediate Similarity	NPD6686	Approved
0.7182	Intermediate Similarity	NPD4700	Approved
0.717	Intermediate Similarity	NPD6050	Approved
0.717	Intermediate Similarity	NPD5694	Approved
0.717	Intermediate Similarity	NPD7637	Suspended
0.7167	Intermediate Similarity	NPD7100	Approved
0.7167	Intermediate Similarity	NPD7101	Approved
0.7143	Intermediate Similarity	NPD6673	Approved
0.7143	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD6317	Approved
0.7143	Intermediate Similarity	NPD6080	Approved
0.7143	Intermediate Similarity	NPD6904	Approved
0.713	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4223	Phase 3
0.7129	Intermediate Similarity	NPD4221	Approved
0.7115	Intermediate Similarity	NPD3573	Approved
0.71	Intermediate Similarity	NPD7525	Registered
0.7087	Intermediate Similarity	NPD5329	Approved
0.7083	Intermediate Similarity	NPD6313	Approved
0.7083	Intermediate Similarity	NPD6314	Approved
0.7075	Intermediate Similarity	NPD5207	Approved
0.7075	Intermediate Similarity	NPD5692	Phase 3
0.7063	Intermediate Similarity	NPD7319	Approved
0.7059	Intermediate Similarity	NPD6274	Approved
0.7043	Intermediate Similarity	NPD4730	Approved
0.7043	Intermediate Similarity	NPD4729	Approved
0.7043	Intermediate Similarity	NPD5168	Approved
0.7041	Intermediate Similarity	NPD6117	Approved
0.7027	Intermediate Similarity	NPD6404	Discontinued
0.7019	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5280	Approved
0.7019	Intermediate Similarity	NPD5690	Phase 2
0.7019	Intermediate Similarity	NPD4694	Approved
0.701	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6411	Approved
0.6991	Remote Similarity	NPD4754	Approved
0.699	Remote Similarity	NPD3668	Phase 3
0.699	Remote Similarity	NPD4197	Approved
0.6984	Remote Similarity	NPD7736	Approved
0.6981	Remote Similarity	NPD6051	Approved
0.697	Remote Similarity	NPD6116	Phase 1
0.6967	Remote Similarity	NPD6319	Approved
0.6957	Remote Similarity	NPD6412	Phase 2
0.6942	Remote Similarity	NPD7328	Approved
0.6942	Remote Similarity	NPD7327	Approved
0.6935	Remote Similarity	NPD7604	Phase 2
0.6931	Remote Similarity	NPD4695	Discontinued
0.6923	Remote Similarity	NPD4634	Approved
0.6923	Remote Similarity	NPD5248	Approved
0.6923	Remote Similarity	NPD5363	Approved
0.6923	Remote Similarity	NPD5247	Approved
0.6923	Remote Similarity	NPD5135	Approved
0.6923	Remote Similarity	NPD5249	Phase 3
0.6923	Remote Similarity	NPD5169	Approved
0.6923	Remote Similarity	NPD5250	Approved
0.6923	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5251	Approved
0.6911	Remote Similarity	NPD5983	Phase 2
0.6911	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6114	Approved
0.69	Remote Similarity	NPD6115	Approved
0.69	Remote Similarity	NPD6118	Approved
0.69	Remote Similarity	NPD3617	Approved
0.69	Remote Similarity	NPD6697	Approved
0.6897	Remote Similarity	NPD5128	Approved
0.6893	Remote Similarity	NPD5362	Discontinued
0.6887	Remote Similarity	NPD5208	Approved
0.6885	Remote Similarity	NPD7516	Approved
0.688	Remote Similarity	NPD7492	Approved
0.687	Remote Similarity	NPD4767	Approved
0.687	Remote Similarity	NPD6008	Approved
0.687	Remote Similarity	NPD4768	Approved
0.6864	Remote Similarity	NPD5127	Approved
0.6864	Remote Similarity	NPD5215	Approved
0.6864	Remote Similarity	NPD5217	Approved
0.6864	Remote Similarity	NPD5216	Approved
0.6857	Remote Similarity	NPD4519	Discontinued
0.6857	Remote Similarity	NPD4688	Approved
0.6857	Remote Similarity	NPD4693	Phase 3
0.6857	Remote Similarity	NPD4689	Approved
0.6857	Remote Similarity	NPD6098	Approved
0.6857	Remote Similarity	NPD5205	Approved
0.6857	Remote Similarity	NPD4138	Approved
0.6857	Remote Similarity	NPD4623	Approved
0.6857	Remote Similarity	NPD4690	Approved
0.6838	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4058	Approved
0.6832	Remote Similarity	NPD4195	Approved
0.6829	Remote Similarity	NPD8294	Approved
0.6829	Remote Similarity	NPD6054	Approved
0.6829	Remote Similarity	NPD8377	Approved
0.6825	Remote Similarity	NPD6336	Discontinued
0.6825	Remote Similarity	NPD6616	Approved
0.6822	Remote Similarity	NPD6101	Approved
0.6822	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5778	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