NPASS Compound

Structure

CID278681 OpenBabel06191716082D 30 35 0 0 1 0 0 0 0 0999 V2000 -2.5091 2.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7053 2.6791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6213 1.8695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8111 1.4020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6398 2.6791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6217 4.6748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8080 3.2730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6183 2.8056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8117 4.2078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4316 3.2719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7053 1.0606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0021 3.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2381 1.8699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6216 2.8049 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4316 4.2069 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0014 2.8054 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0011 1.8699 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1070 1.8699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4288 1.4026 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4286 0.4682 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6191 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6186 1.8701 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8117 3.2729 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8091 1.4024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2865 4.6299 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2977 4.7067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0415 1.8699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2947 -0.0317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6398 1.0606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 5 2 0 0 0 0 2 13 1 0 0 0 0 3 4 1 0 0 0 0 3 14 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 9 1 0 0 0 0 6 15 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 13 2 0 0 0 0 11 29 1 0 0 0 0 12 25 1 0 0 0 0 13 19 1 0 0 0 0 14 23 1 1 0 0 0 15 26 1 6 0 0 0 16 17 1 0 0 0 0 16 23 1 6 0 0 0 17 24 1 1 0 0 0 18 27 2 0 0 0 0 18 29 1 0 0 0 0 19 20 1 0 0 0 0 19 22 1 6 0 0 0 20 21 1 0 0 0 0 20 28 1 6 0 0 0 21 24 1 1 0 0 0 21 30 1 0 0 0 0 22 24 1 6 0 0 0 23 12 1 6 0 0 0 24 30 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.22
Volume:	417.153
LogP:	2.008
LogD:	2.245
LogS:	-3.596
# Rotatable Bonds:	2
TPSA:	103.43
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.639
Synthetic Accessibility Score:	5.401
Fsp3:	0.792
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.346
MDCK Permeability:	2.546954056015238e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.117
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.296
Plasma Protein Binding (PPB):	91.03826141357422%
Volume Distribution (VD):	1.268
Pgp-substrate:	7.121382713317871%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.579
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.505
CYP2C9-inhibitor:	0.067
CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.275
CYP3A4-inhibitor:	0.597
CYP3A4-substrate:	0.179

ADMET: Excretion

Clearance (CL):	9.625
Half-life (T1/2):	0.514

ADMET: Toxicity

hERG Blockers:	0.404
Human Hepatotoxicity (H-HT):	0.844
Drug-inuced Liver Injury (DILI):	0.232
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.879
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.352
Carcinogencity:	0.385
Eye Corrosion:	0.011
Eye Irritation:	0.093
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC278681

Natural Product ID:	NPC278681
*Common Name:**	XDCJWJYMHNAEQH-DFJCLZAPSA-N
IUPAC Name:	n.a.
Synonyms:	19-Hydroxydesacetylcinobufagin
Standard InCHIKey:	XDCJWJYMHNAEQH-DFJCLZAPSA-N
Standard InCHI:	InChI=1S/C24H32O6/c1-22-8-7-16-17(4-3-14-10-15(26)6-9-23(14,16)12-25)24(22)21(30-24)20(28)19(22)13-2-5-18(27)29-11-13/h2,5,11,14-17,19-21,25-26,28H,3-4,6-10,12H2,1H3/t14-,15+,16+,17-,19+,20-,21-,22-,23-,24-/m1/s1
SMILES:	C[C@@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@H](CC[C@]34CO)O)[C@]32[C@@H]([C@@H]([C@@H]1c1ccc(=O)oc1)O)O3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518554
PubChem CID:	15513543
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]
NPO33241	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575946]
NPO33241	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141860]
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]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	venom	n.a.	n.a.	PMID[24050254]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26722868]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28256122]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223924]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8733	Duttaphrynus melanostictus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9576	Bufo bufo	Species	Bufonidae	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]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
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]
NPO10043	Phebalium ozothamnoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	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]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12735	Halimeda macroloba	Species	Halimedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8733	Duttaphrynus melanostictus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2498	Kochia trichophylla	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9398	Cortinarius rubellus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11981	Bufo gargarizans	Species	Bufonidae	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]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7884	Centaurea amara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO664	Potentilla multifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11515	Streptomyces plumbeus	Species	Streptomycetaceae	Bacteria	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	3.9	ug.mL-1	PMID[512516]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	0.49	ug.mL-1	PMID[512516]
NPT1366	Cell Line	MH60	Mus musculus	IC50	>	25.0	ug.mL-1	PMID[512516]

☑ 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 NPC278681 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	391
0.1-0.2	1419
0.2-0.3	2930
0.3-0.4	5428
0.4-0.5	10162
0.5-0.6	10121
0.6-0.7	9764
0.7-0.8	2117
0.8-0.85	282
0.85-0.9	37
0.9-0.95	30
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9909	High Similarity	NPC112936
0.9908	High Similarity	NPC16701
0.9818	High Similarity	NPC35171
0.9818	High Similarity	NPC213761
0.9817	High Similarity	NPC157380
0.9817	High Similarity	NPC185287
0.9364	High Similarity	NPC171126
0.9298	High Similarity	NPC312481
0.9273	High Similarity	NPC44537
0.9266	High Similarity	NPC103491
0.9174	High Similarity	NPC75389
0.9138	High Similarity	NPC6193
0.9083	High Similarity	NPC275060
0.8991	High Similarity	NPC79298
0.8991	High Similarity	NPC43063
0.8983	High Similarity	NPC159499
0.8919	High Similarity	NPC12795
0.8909	High Similarity	NPC304276
0.8909	High Similarity	NPC137462
0.8727	High Similarity	NPC295843
0.8716	High Similarity	NPC171014
0.8684	High Similarity	NPC241977
0.8673	High Similarity	NPC470076
0.8559	High Similarity	NPC41123
0.8559	High Similarity	NPC220217
0.8559	High Similarity	NPC119855
0.8559	High Similarity	NPC145074
0.8559	High Similarity	NPC257610
0.8559	High Similarity	NPC114939
0.8534	High Similarity	NPC113425
0.8534	High Similarity	NPC232564
0.8522	High Similarity	NPC154815
0.8509	High Similarity	NPC183603
0.8487	Intermediate Similarity	NPC233500
0.8475	Intermediate Similarity	NPC219656
0.8475	Intermediate Similarity	NPC153085
0.8475	Intermediate Similarity	NPC268326
0.8468	Intermediate Similarity	NPC165969
0.8462	Intermediate Similarity	NPC290693
0.8448	Intermediate Similarity	NPC216665
0.8435	Intermediate Similarity	NPC247760
0.8417	Intermediate Similarity	NPC196130
0.8417	Intermediate Similarity	NPC115349
0.8403	Intermediate Similarity	NPC79579
0.8393	Intermediate Similarity	NPC265502
0.8393	Intermediate Similarity	NPC469960
0.8393	Intermediate Similarity	NPC186668
0.8393	Intermediate Similarity	NPC93026
0.8393	Intermediate Similarity	NPC29389
0.8378	Intermediate Similarity	NPC472821
0.8376	Intermediate Similarity	NPC470075
0.8361	Intermediate Similarity	NPC179261
0.8348	Intermediate Similarity	NPC71680
0.8347	Intermediate Similarity	NPC219804
0.8333	Intermediate Similarity	NPC67569
0.8319	Intermediate Similarity	NPC29639
0.8319	Intermediate Similarity	NPC305260
0.8319	Intermediate Similarity	NPC304260
0.8319	Intermediate Similarity	NPC469959
0.8319	Intermediate Similarity	NPC44899
0.8319	Intermediate Similarity	NPC472263
0.8319	Intermediate Similarity	NPC5883
0.8319	Intermediate Similarity	NPC108682
0.8319	Intermediate Similarity	NPC270850
0.8319	Intermediate Similarity	NPC469957
0.8306	Intermediate Similarity	NPC221414
0.8304	Intermediate Similarity	NPC472822
0.8291	Intermediate Similarity	NPC471633
0.8291	Intermediate Similarity	NPC43213
0.8291	Intermediate Similarity	NPC84949
0.8291	Intermediate Similarity	NPC69576
0.8291	Intermediate Similarity	NPC31354
0.8288	Intermediate Similarity	NPC470972
0.8279	Intermediate Similarity	NPC8374
0.8264	Intermediate Similarity	NPC23786
0.8264	Intermediate Similarity	NPC471082
0.8264	Intermediate Similarity	NPC470265
0.8261	Intermediate Similarity	NPC16270
0.8261	Intermediate Similarity	NPC15551
0.825	Intermediate Similarity	NPC474370
0.8235	Intermediate Similarity	NPC146786
0.8235	Intermediate Similarity	NPC153440
0.823	Intermediate Similarity	NPC470980
0.822	Intermediate Similarity	NPC5311
0.822	Intermediate Similarity	NPC99620
0.822	Intermediate Similarity	NPC310341
0.822	Intermediate Similarity	NPC193382
0.822	Intermediate Similarity	NPC199428
0.8217	Intermediate Similarity	NPC75616
0.8214	Intermediate Similarity	NPC10232
0.8214	Intermediate Similarity	NPC196471
0.8214	Intermediate Similarity	NPC160583
0.8214	Intermediate Similarity	NPC187302
0.8214	Intermediate Similarity	NPC189588
0.8214	Intermediate Similarity	NPC97487
0.8198	Intermediate Similarity	NPC295110
0.8198	Intermediate Similarity	NPC268829
0.8198	Intermediate Similarity	NPC475617
0.8198	Intermediate Similarity	NPC222875
0.8198	Intermediate Similarity	NPC247701
0.8198	Intermediate Similarity	NPC25177
0.8197	Intermediate Similarity	NPC469789
0.8197	Intermediate Similarity	NPC55602
0.8182	Intermediate Similarity	NPC231518
0.8182	Intermediate Similarity	NPC475219
0.8167	Intermediate Similarity	NPC264954
0.8167	Intermediate Similarity	NPC5292
0.8165	Intermediate Similarity	NPC299654
0.8158	Intermediate Similarity	NPC472820
0.8151	Intermediate Similarity	NPC471351
0.8151	Intermediate Similarity	NPC203862
0.8151	Intermediate Similarity	NPC471355
0.8151	Intermediate Similarity	NPC243196
0.8151	Intermediate Similarity	NPC77319
0.8151	Intermediate Similarity	NPC152615
0.8151	Intermediate Similarity	NPC27507
0.8151	Intermediate Similarity	NPC84987
0.8151	Intermediate Similarity	NPC34390
0.8151	Intermediate Similarity	NPC158344
0.8151	Intermediate Similarity	NPC244402
0.8151	Intermediate Similarity	NPC309034
0.8151	Intermediate Similarity	NPC99728
0.8151	Intermediate Similarity	NPC50305
0.8151	Intermediate Similarity	NPC87250
0.8151	Intermediate Similarity	NPC196429
0.8151	Intermediate Similarity	NPC93883
0.8151	Intermediate Similarity	NPC471354
0.8151	Intermediate Similarity	NPC471353
0.8151	Intermediate Similarity	NPC142066
0.8151	Intermediate Similarity	NPC157376
0.8151	Intermediate Similarity	NPC474418
0.8151	Intermediate Similarity	NPC473852
0.8142	Intermediate Similarity	NPC200861
0.8136	Intermediate Similarity	NPC305044
0.8136	Intermediate Similarity	NPC265290
0.8125	Intermediate Similarity	NPC158350
0.812	Intermediate Similarity	NPC150228
0.812	Intermediate Similarity	NPC214005
0.812	Intermediate Similarity	NPC241477
0.8115	Intermediate Similarity	NPC193893
0.8115	Intermediate Similarity	NPC88326
0.8115	Intermediate Similarity	NPC153700
0.8115	Intermediate Similarity	NPC107493
0.8108	Intermediate Similarity	NPC79631
0.8103	Intermediate Similarity	NPC177047
0.8099	Intermediate Similarity	NPC474585
0.8099	Intermediate Similarity	NPC184555
0.8087	Intermediate Similarity	NPC50124
0.8083	Intermediate Similarity	NPC83287
0.8083	Intermediate Similarity	NPC472080
0.8083	Intermediate Similarity	NPC709
0.8083	Intermediate Similarity	NPC50774
0.807	Intermediate Similarity	NPC472818
0.807	Intermediate Similarity	NPC471206
0.8067	Intermediate Similarity	NPC298278
0.8067	Intermediate Similarity	NPC190286
0.8065	Intermediate Similarity	NPC293112
0.8062	Intermediate Similarity	NPC62172
0.8062	Intermediate Similarity	NPC289700
0.8053	Intermediate Similarity	NPC474124
0.8053	Intermediate Similarity	NPC297617
0.8051	Intermediate Similarity	NPC73050
0.8051	Intermediate Similarity	NPC101965
0.8051	Intermediate Similarity	NPC101400
0.8049	Intermediate Similarity	NPC11895
0.8036	Intermediate Similarity	NPC155974
0.8034	Intermediate Similarity	NPC262083
0.8034	Intermediate Similarity	NPC255401
0.8034	Intermediate Similarity	NPC471484
0.8034	Intermediate Similarity	NPC284162
0.8033	Intermediate Similarity	NPC40749
0.8033	Intermediate Similarity	NPC46570
0.8031	Intermediate Similarity	NPC155529
0.8018	Intermediate Similarity	NPC278673
0.8018	Intermediate Similarity	NPC65700
0.8017	Intermediate Similarity	NPC30483
0.8017	Intermediate Similarity	NPC475041
0.8017	Intermediate Similarity	NPC81222
0.8017	Intermediate Similarity	NPC292467
0.8017	Intermediate Similarity	NPC470897
0.8017	Intermediate Similarity	NPC329905
0.8017	Intermediate Similarity	NPC291820
0.8017	Intermediate Similarity	NPC475030
0.8017	Intermediate Similarity	NPC55532
0.8017	Intermediate Similarity	NPC236973
0.8017	Intermediate Similarity	NPC32177
0.8017	Intermediate Similarity	NPC469756
0.8	Intermediate Similarity	NPC140055
0.8	Intermediate Similarity	NPC470492
0.8	Intermediate Similarity	NPC286528
0.8	Intermediate Similarity	NPC20302
0.8	Intermediate Similarity	NPC167606
0.7984	Intermediate Similarity	NPC81736
0.7984	Intermediate Similarity	NPC172154
0.7984	Intermediate Similarity	NPC8369
0.7982	Intermediate Similarity	NPC473543
0.7982	Intermediate Similarity	NPC472819
0.7967	Intermediate Similarity	NPC170538
0.7966	Intermediate Similarity	NPC470063
0.7966	Intermediate Similarity	NPC98038

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 NPC278681 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	855
0.2-0.3	1770
0.3-0.4	2662
0.4-0.5	2137
0.5-0.6	1018
0.6-0.7	346
0.7-0.8	26
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8644	High Similarity	NPD7503	Approved
0.8182	Intermediate Similarity	NPD8033	Approved
0.8083	Intermediate Similarity	NPD7327	Approved
0.8083	Intermediate Similarity	NPD7328	Approved
0.8017	Intermediate Similarity	NPD7516	Approved
0.8	Intermediate Similarity	NPD7115	Discovery
0.7951	Intermediate Similarity	NPD8377	Approved
0.7951	Intermediate Similarity	NPD8294	Approved
0.7886	Intermediate Similarity	NPD8378	Approved
0.7886	Intermediate Similarity	NPD8296	Approved
0.7886	Intermediate Similarity	NPD8380	Approved
0.7886	Intermediate Similarity	NPD8379	Approved
0.7886	Intermediate Similarity	NPD8335	Approved
0.7857	Intermediate Similarity	NPD7638	Approved
0.7788	Intermediate Similarity	NPD7640	Approved
0.7788	Intermediate Similarity	NPD7639	Approved
0.7638	Intermediate Similarity	NPD7507	Approved
0.7565	Intermediate Similarity	NPD5344	Discontinued
0.7478	Intermediate Similarity	NPD6648	Approved
0.7462	Intermediate Similarity	NPD7319	Approved
0.7381	Intermediate Similarity	NPD6319	Approved
0.7377	Intermediate Similarity	NPD6053	Discontinued
0.7317	Intermediate Similarity	NPD4632	Approved
0.7273	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD7736	Approved
0.7241	Intermediate Similarity	NPD4225	Approved
0.7236	Intermediate Similarity	NPD8297	Approved
0.7232	Intermediate Similarity	NPD7838	Discovery
0.7203	Intermediate Similarity	NPD7632	Discontinued
0.719	Intermediate Similarity	NPD6899	Approved
0.719	Intermediate Similarity	NPD6881	Approved
0.7154	Intermediate Similarity	NPD7492	Approved
0.7109	Intermediate Similarity	NPD6054	Approved
0.7107	Intermediate Similarity	NPD5697	Approved
0.7099	Intermediate Similarity	NPD6616	Approved
0.7077	Intermediate Similarity	NPD7604	Phase 2
0.7073	Intermediate Similarity	NPD6883	Approved
0.7073	Intermediate Similarity	NPD7102	Approved
0.7073	Intermediate Similarity	NPD7290	Approved
0.7049	Intermediate Similarity	NPD6686	Approved
0.7045	Intermediate Similarity	NPD7078	Approved
0.7025	Intermediate Similarity	NPD6402	Approved
0.7025	Intermediate Similarity	NPD7128	Approved
0.7025	Intermediate Similarity	NPD6008	Approved
0.7025	Intermediate Similarity	NPD5739	Approved
0.7025	Intermediate Similarity	NPD6675	Approved
0.7016	Intermediate Similarity	NPD8130	Phase 1
0.7016	Intermediate Similarity	NPD6847	Approved
0.7016	Intermediate Similarity	NPD6649	Approved
0.7016	Intermediate Similarity	NPD6617	Approved
0.7016	Intermediate Similarity	NPD6650	Approved
0.7016	Intermediate Similarity	NPD6869	Approved
0.7008	Intermediate Similarity	NPD6009	Approved
0.7	Intermediate Similarity	NPD6370	Approved
0.6992	Remote Similarity	NPD6014	Approved
0.6992	Remote Similarity	NPD6013	Approved
0.6992	Remote Similarity	NPD6012	Approved
0.6967	Remote Similarity	NPD6412	Phase 2
0.6964	Remote Similarity	NPD7524	Approved
0.696	Remote Similarity	NPD6882	Approved
0.6935	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4634	Approved
0.6923	Remote Similarity	NPD5983	Phase 2
0.6923	Remote Similarity	NPD6016	Approved
0.6923	Remote Similarity	NPD6015	Approved
0.6911	Remote Similarity	NPD6011	Approved
0.6911	Remote Similarity	NPD7320	Approved
0.6905	Remote Similarity	NPD8133	Approved
0.687	Remote Similarity	NPD5988	Approved
0.687	Remote Similarity	NPD7637	Suspended
0.6855	Remote Similarity	NPD6372	Approved
0.6855	Remote Similarity	NPD6373	Approved
0.6847	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6059	Approved
0.6842	Remote Similarity	NPD6051	Approved
0.6842	Remote Similarity	NPD6336	Discontinued
0.6833	Remote Similarity	NPD4159	Approved
0.6829	Remote Similarity	NPD5701	Approved
0.68	Remote Similarity	NPD6371	Approved
0.6791	Remote Similarity	NPD8293	Discontinued
0.6789	Remote Similarity	NPD7525	Registered
0.6777	Remote Similarity	NPD5211	Phase 2
0.6757	Remote Similarity	NPD6695	Phase 3
0.675	Remote Similarity	NPD5285	Approved
0.675	Remote Similarity	NPD5286	Approved
0.675	Remote Similarity	NPD4696	Approved
0.6723	Remote Similarity	NPD6084	Phase 2
0.6723	Remote Similarity	NPD6083	Phase 2
0.6694	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5141	Approved
0.6641	Remote Similarity	NPD7101	Approved
0.6641	Remote Similarity	NPD7100	Approved
0.6639	Remote Similarity	NPD4633	Approved
0.6639	Remote Similarity	NPD5226	Approved
0.6639	Remote Similarity	NPD5224	Approved
0.6639	Remote Similarity	NPD5225	Approved
0.6638	Remote Similarity	NPD6698	Approved
0.6638	Remote Similarity	NPD46	Approved
0.6614	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5174	Approved
0.6585	Remote Similarity	NPD5175	Approved
0.6583	Remote Similarity	NPD4755	Approved
0.6565	Remote Similarity	NPD6335	Approved
0.6557	Remote Similarity	NPD5223	Approved
0.6541	Remote Similarity	NPD8513	Phase 3
0.6538	Remote Similarity	NPD6274	Approved
0.6531	Remote Similarity	NPD7625	Phase 1
0.6529	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6399	Phase 3
0.6525	Remote Similarity	NPD4202	Approved
0.6522	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4250	Approved
0.6522	Remote Similarity	NPD4251	Approved
0.6522	Remote Similarity	NPD7750	Discontinued
0.6508	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6317	Approved
0.6486	Remote Similarity	NPD6931	Approved
0.6486	Remote Similarity	NPD6930	Phase 2
0.6486	Remote Similarity	NPD7514	Phase 3
0.6475	Remote Similarity	NPD7260	Phase 2
0.6475	Remote Similarity	NPD4700	Approved
0.6471	Remote Similarity	NPD7748	Approved
0.6466	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7902	Approved
0.6443	Remote Similarity	NPD7236	Approved
0.6441	Remote Similarity	NPD6079	Approved
0.6441	Remote Similarity	NPD5284	Approved
0.6441	Remote Similarity	NPD7515	Phase 2
0.6441	Remote Similarity	NPD8035	Phase 2
0.6441	Remote Similarity	NPD5281	Approved
0.6441	Remote Similarity	NPD8034	Phase 2
0.6439	Remote Similarity	NPD6314	Approved
0.6439	Remote Similarity	NPD6313	Approved
0.6435	Remote Similarity	NPD4249	Approved
0.6429	Remote Similarity	NPD6902	Approved
0.6429	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6933	Approved
0.6418	Remote Similarity	NPD8517	Approved
0.6418	Remote Similarity	NPD8515	Approved
0.6418	Remote Similarity	NPD8516	Approved
0.6417	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD5695	Phase 3
0.6396	Remote Similarity	NPD4195	Approved
0.6396	Remote Similarity	NPD6929	Approved
0.6393	Remote Similarity	NPD5696	Approved
0.6378	Remote Similarity	NPD4730	Approved
0.6378	Remote Similarity	NPD4729	Approved
0.6377	Remote Similarity	NPD6033	Approved
0.6364	Remote Similarity	NPD6932	Approved
0.6348	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7332	Phase 2
0.6324	Remote Similarity	NPD6067	Discontinued
0.6324	Remote Similarity	NPD8328	Phase 3
0.6306	Remote Similarity	NPD7145	Approved
0.6303	Remote Similarity	NPD5693	Phase 1
0.6303	Remote Similarity	NPD7087	Discontinued
0.6296	Remote Similarity	NPD6908	Approved
0.6296	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6909	Approved
0.6293	Remote Similarity	NPD7146	Approved
0.6293	Remote Similarity	NPD6409	Approved
0.6293	Remote Similarity	NPD7334	Approved
0.6293	Remote Similarity	NPD5330	Approved
0.6293	Remote Similarity	NPD7521	Approved
0.6293	Remote Similarity	NPD6684	Approved
0.6281	Remote Similarity	NPD5210	Approved
0.6281	Remote Similarity	NPD4629	Approved
0.6279	Remote Similarity	NPD5250	Approved
0.6279	Remote Similarity	NPD5247	Approved
0.6279	Remote Similarity	NPD5251	Approved
0.6279	Remote Similarity	NPD5248	Approved
0.6279	Remote Similarity	NPD5249	Phase 3
0.6273	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5328	Approved
0.6271	Remote Similarity	NPD4753	Phase 2
0.625	Remote Similarity	NPD7645	Phase 2
0.625	Remote Similarity	NPD5128	Approved
0.6239	Remote Similarity	NPD6924	Approved
0.6239	Remote Similarity	NPD6926	Approved
0.6234	Remote Similarity	NPD7239	Suspended
0.6231	Remote Similarity	NPD5215	Approved
0.6231	Remote Similarity	NPD5216	Approved
0.6231	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD5217	Approved
0.623	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5222	Approved
0.623	Remote Similarity	NPD5221	Approved
0.622	Remote Similarity	NPD4767	Approved
0.622	Remote Similarity	NPD7799	Discontinued
0.622	Remote Similarity	NPD4768	Approved
0.6218	Remote Similarity	NPD5785	Approved
0.6216	Remote Similarity	NPD5776	Phase 2
0.6216	Remote Similarity	NPD6925	Approved
0.6207	Remote Similarity	NPD6893	Approved
0.6202	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7900	Approved
0.6195	Remote Similarity	NPD4822	Approved
0.6195	Remote Similarity	NPD4821	Approved
0.6195	Remote Similarity	NPD4819	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