NPASS Compound

Structure

CID86893 OpenBabel06191715422D 40 42 0 0 1 0 0 0 0 0999 V2000 -3.7826 0.0865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -4.3953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2294 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0450 3.1779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8786 -0.2092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8091 -0.3264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5502 -0.8070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4219 -2.0434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -2.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1076 -0.6195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -3.9070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3835 -0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2623 2.2256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -1.4651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2820 -1.5805 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6918 -0.9767 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 -2.1397 -0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9767 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7159 0.3916 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7636 -1.5857 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7636 0.6090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7415 -1.3008 0.0000 C 0 0 0 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 -1.7159 -1.3684 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8459 -4.3953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3835 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 2.9302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1957 1.9377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1620 -2.0043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3249 1.1553 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5463 -2.5380 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1957 -2.1108 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -2.9302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -1.4651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 1.4651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5463 1.5612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 26 1 0 0 0 0 7 26 1 0 0 0 0 9 19 1 0 0 0 0 9 20 1 0 0 0 0 10 18 1 0 0 0 0 10 28 1 0 0 0 0 11 37 1 0 0 0 0 12 18 1 0 0 0 0 12 21 2 0 0 0 0 13 29 2 0 0 0 0 13 37 1 0 0 0 0 14 30 2 0 0 0 0 14 38 1 0 0 0 0 15 31 2 0 0 0 0 15 39 1 0 0 0 0 16 32 2 0 0 0 0 16 40 1 0 0 0 0 17 11 1 1 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 18 33 1 6 0 0 0 19 38 1 6 0 0 0 20 27 1 1 0 0 0 20 39 1 0 0 0 0 21 23 1 0 0 0 0 21 28 1 0 0 0 0 22 24 1 0 0 0 0 22 27 1 1 0 0 0 23 25 1 0 0 0 0 23 34 1 1 0 0 0 24 28 1 6 0 0 0 24 35 1 0 0 0 0 25 27 1 6 0 0 0 25 40 1 0 0 0 0 26 36 1 0 0 0 0 27 8 1 1 0 0 0 28 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	570.27
Volume:	559.475
LogP:	0.451
LogD:	0.784
LogS:	-3.206
# Rotatable Bonds:	10
TPSA:	186.12
# H-Bond Aceptor:	12
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.198
Synthetic Accessibility Score:	5.292
Fsp3:	0.786
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.64
MDCK Permeability:	0.00018438095867168158
Pgp-inhibitor:	0.979
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.982
20% Bioavailability (F20%):	0.082
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	28.887996673583984%
Volume Distribution (VD):	0.808
Pgp-substrate:	38.88456344604492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.126
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.141
CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.077
CYP3A4-substrate:	0.248

ADMET: Excretion

Clearance (CL):	2.164
Half-life (T1/2):	0.886

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.308
Drug-inuced Liver Injury (DILI):	0.784
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.3
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.1
Carcinogencity:	0.119
Eye Corrosion:	0.004
Eye Irritation:	0.019
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC86893

Natural Product ID:	NPC86893
*Common Name:**	Taxumairol V
IUPAC Name:	[(2S,4R,5R,5aS,6S,8S,9R,9aR,10S,10aS)-5,6,8-triacetyloxy-2,4,10-trihydroxy-10a-(2-hydroxypropan-2-yl)-3,5a-dimethyl-1,2,4,5,6,7,8,9,9a,10-decahydrobenzo[f]azulen-9-yl]methyl acetate
Synonyms:	taxumairol V
Standard InCHIKey:	TXBJKSOTSLHNLL-ZOAIKBMOSA-N
Standard InCHI:	InChI=1S/C28H42O12/c1-12-18(33)10-28(26(6,7)36)21(12)23(34)25(40-16(5)32)27(8)20(39-15(4)31)9-19(38-14(3)30)17(11-37-13(2)29)22(27)24(28)35/h17-20,22-25,33-36H,9-11H2,1-8H3/t17-,18+,19+,20+,22+,23-,24+,25+,27-,28+/m1/s1
SMILES:	CC1=C2[C@H]([C@@H]([C@]3(C)[C@H](C[C@@H]([C@@H](COC(=O)C)[C@H]3[C@@H]([C@@]2(C[C@@H]1O)C(C)(C)O)O)OC(=O)C)OC(=O)C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481270
PubChem CID:	10875480
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes 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
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/j.tet.2004.10.110]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1016/j.tet.2004.10.110]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[11473432]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[12502326]
NPO25366	Sapium indicum	Species	Euphorbiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[12713411]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	twig	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679325]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124776]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[17907781]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18220355]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18804027]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[19646881]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20233596]
NPO25054	Phaleria macrocarpa	Species	Thymelaeaceae	Eukaryota	nut shell	n.a.	n.a.	PMID[23044367]
NPO25252	Nannocystis exedens	Species	Nannocystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24460410]
NPO25311	Guettarda platypoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2553871]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32058711]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8557595]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[8991951]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644081]
NPO24373	Lobelia inflata	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24278	Pistacia chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24373	Lobelia inflata	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24278	Pistacia chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22283	Alhagi maurorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24852	Helicia nilagirica	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24278	Pistacia chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25492	Botryllus leachi	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22152	Tecoma undulata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22283	Alhagi maurorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18706	Anemone thalictroides	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23994	Ormosia macrophylla	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23894	Pulicaria insignis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25466	Lecanora sulphurella	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14189	Osmundaria spiralis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22618	Psolus eximius	Species	Psolidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25366	Sapium indicum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24373	Lobelia inflata	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24461	Clusia sandiensis	Species	Clusiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24852	Helicia nilagirica	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25054	Phaleria macrocarpa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24607	Goniothalamus dolichocarpus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3721	Achyranthes obtusifolia	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24278	Pistacia chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25311	Guettarda platypoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24882	Erythrophleum chlorostachys	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27390	Vernonia brevifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24802	Diploprion bifasciatum	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25252	Nannocystis exedens	Species	Nannocystaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24730	Lactarius deliciosus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25277	Seiridium cupressi	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20264	Moonia heterophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28460	Achyrocline tomentosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25441	Desmodium pulchellu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15482	Vanderbylia fraxinea	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25389	Allium angulosum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24566	Marasmiellus ramealis	Species	Omphalotaceae	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
Cell Line	1
NON-MOLECULAR	1

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[501352]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.6	ug.mL-1	PMID[501352]

☑ 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 NPC86893 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	226
0.1-0.2	1707
0.2-0.3	4998
0.3-0.4	11703
0.4-0.5	11270
0.5-0.6	7685
0.6-0.7	4502
0.7-0.8	576
0.8-0.85	19
0.85-0.9	5
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC292178
0.9778	High Similarity	NPC254121
0.9565	High Similarity	NPC475877
0.9451	High Similarity	NPC475304
0.9362	High Similarity	NPC165578
0.8947	High Similarity	NPC274643
0.8804	High Similarity	NPC249034
0.8696	High Similarity	NPC209816
0.8485	Intermediate Similarity	NPC475623
0.8485	Intermediate Similarity	NPC473694
0.8485	Intermediate Similarity	NPC475334
0.8444	Intermediate Similarity	NPC222634
0.8438	Intermediate Similarity	NPC129569
0.84	Intermediate Similarity	NPC181104
0.84	Intermediate Similarity	NPC475331
0.84	Intermediate Similarity	NPC475335
0.84	Intermediate Similarity	NPC80809
0.84	Intermediate Similarity	NPC201144
0.84	Intermediate Similarity	NPC103298
0.84	Intermediate Similarity	NPC121518
0.84	Intermediate Similarity	NPC288502
0.8367	Intermediate Similarity	NPC188968
0.8351	Intermediate Similarity	NPC473244
0.8317	Intermediate Similarity	NPC60315
0.8265	Intermediate Similarity	NPC470067
0.8265	Intermediate Similarity	NPC470066
0.8252	Intermediate Similarity	NPC273433
0.8247	Intermediate Similarity	NPC284194
0.8247	Intermediate Similarity	NPC211810
0.8247	Intermediate Similarity	NPC471765
0.8247	Intermediate Similarity	NPC221801
0.8229	Intermediate Similarity	NPC105375
0.8229	Intermediate Similarity	NPC182826
0.8218	Intermediate Similarity	NPC475585
0.8218	Intermediate Similarity	NPC474550
0.8218	Intermediate Similarity	NPC473577
0.8182	Intermediate Similarity	NPC79303
0.8182	Intermediate Similarity	NPC38855
0.8137	Intermediate Similarity	NPC475290
0.81	Intermediate Similarity	NPC472554
0.8081	Intermediate Similarity	NPC470068
0.8058	Intermediate Similarity	NPC473173
0.8058	Intermediate Similarity	NPC469318
0.8041	Intermediate Similarity	NPC472360
0.8041	Intermediate Similarity	NPC472416
0.8039	Intermediate Similarity	NPC473543
0.8021	Intermediate Similarity	NPC114389
0.802	Intermediate Similarity	NPC472552
0.802	Intermediate Similarity	NPC470972
0.802	Intermediate Similarity	NPC470053
0.8	Intermediate Similarity	NPC272223
0.8	Intermediate Similarity	NPC271295
0.798	Intermediate Similarity	NPC120446
0.7979	Intermediate Similarity	NPC44538
0.7959	Intermediate Similarity	NPC476720
0.7957	Intermediate Similarity	NPC471379
0.7957	Intermediate Similarity	NPC196911
0.7941	Intermediate Similarity	NPC474124
0.7941	Intermediate Similarity	NPC473523
0.7938	Intermediate Similarity	NPC137461
0.7938	Intermediate Similarity	NPC110022
0.7921	Intermediate Similarity	NPC470054
0.7921	Intermediate Similarity	NPC475617
0.7917	Intermediate Similarity	NPC471378
0.7917	Intermediate Similarity	NPC312471
0.7895	Intermediate Similarity	NPC470260
0.7895	Intermediate Similarity	NPC476723
0.7895	Intermediate Similarity	NPC75443
0.7895	Intermediate Similarity	NPC476724
0.7879	Intermediate Similarity	NPC306797
0.7879	Intermediate Similarity	NPC111834
0.7879	Intermediate Similarity	NPC169270
0.7879	Intermediate Similarity	NPC292718
0.7872	Intermediate Similarity	NPC475684
0.787	Intermediate Similarity	NPC216665
0.7857	Intermediate Similarity	NPC39453
0.7857	Intermediate Similarity	NPC473258
0.7849	Intermediate Similarity	NPC102048
0.7843	Intermediate Similarity	NPC474709
0.7843	Intermediate Similarity	NPC476471
0.7843	Intermediate Similarity	NPC475344
0.7835	Intermediate Similarity	NPC91251
0.7812	Intermediate Similarity	NPC115607
0.7812	Intermediate Similarity	NPC246028
0.7812	Intermediate Similarity	NPC291875
0.781	Intermediate Similarity	NPC472219
0.781	Intermediate Similarity	NPC472217
0.781	Intermediate Similarity	NPC38948
0.781	Intermediate Similarity	NPC472218
0.781	Intermediate Similarity	NPC50124
0.78	Intermediate Similarity	NPC475033
0.78	Intermediate Similarity	NPC475032
0.7789	Intermediate Similarity	NPC471779
0.7789	Intermediate Similarity	NPC245004
0.7788	Intermediate Similarity	NPC470980
0.7778	Intermediate Similarity	NPC241047
0.7778	Intermediate Similarity	NPC276110
0.7767	Intermediate Similarity	NPC474822
0.7757	Intermediate Similarity	NPC475668
0.7757	Intermediate Similarity	NPC475480
0.7757	Intermediate Similarity	NPC473921
0.7755	Intermediate Similarity	NPC472640
0.7755	Intermediate Similarity	NPC53555
0.7755	Intermediate Similarity	NPC27918
0.7755	Intermediate Similarity	NPC472641
0.7745	Intermediate Similarity	NPC96784
0.7745	Intermediate Similarity	NPC11974
0.7745	Intermediate Similarity	NPC235920
0.7742	Intermediate Similarity	NPC5958
0.7736	Intermediate Similarity	NPC42662
0.7736	Intermediate Similarity	NPC206618
0.7732	Intermediate Similarity	NPC220216
0.7732	Intermediate Similarity	NPC48732
0.7714	Intermediate Similarity	NPC187435
0.7714	Intermediate Similarity	NPC122816
0.7714	Intermediate Similarity	NPC471205
0.7714	Intermediate Similarity	NPC475781
0.7714	Intermediate Similarity	NPC472390
0.7714	Intermediate Similarity	NPC67321
0.7708	Intermediate Similarity	NPC92370
0.7706	Intermediate Similarity	NPC43213
0.7706	Intermediate Similarity	NPC472400
0.77	Intermediate Similarity	NPC103165
0.77	Intermediate Similarity	NPC471903
0.77	Intermediate Similarity	NPC472995
0.77	Intermediate Similarity	NPC210717
0.7692	Intermediate Similarity	NPC470064
0.7692	Intermediate Similarity	NPC470057
0.7692	Intermediate Similarity	NPC470059
0.7692	Intermediate Similarity	NPC470043
0.7692	Intermediate Similarity	NPC470060
0.7692	Intermediate Similarity	NPC470061
0.7692	Intermediate Similarity	NPC470058
0.7692	Intermediate Similarity	NPC470768
0.7692	Intermediate Similarity	NPC152966
0.7692	Intermediate Similarity	NPC470062
0.7684	Intermediate Similarity	NPC476217
0.7677	Intermediate Similarity	NPC474922
0.767	Intermediate Similarity	NPC295791
0.767	Intermediate Similarity	NPC469316
0.767	Intermediate Similarity	NPC11956
0.7667	Intermediate Similarity	NPC31037
0.7664	Intermediate Similarity	NPC475134
0.7664	Intermediate Similarity	NPC475563
0.7664	Intermediate Similarity	NPC250956
0.7664	Intermediate Similarity	NPC177047
0.7664	Intermediate Similarity	NPC475463
0.7653	Intermediate Similarity	NPC122057
0.7653	Intermediate Similarity	NPC219516
0.7653	Intermediate Similarity	NPC124374
0.7647	Intermediate Similarity	NPC474718
0.7647	Intermediate Similarity	NPC230546
0.7647	Intermediate Similarity	NPC473510
0.7642	Intermediate Similarity	NPC181994
0.7636	Intermediate Similarity	NPC470075
0.7629	Intermediate Similarity	NPC97103
0.7629	Intermediate Similarity	NPC261320
0.7629	Intermediate Similarity	NPC20946
0.7629	Intermediate Similarity	NPC161560
0.7624	Intermediate Similarity	NPC274793
0.7624	Intermediate Similarity	NPC261807
0.7624	Intermediate Similarity	NPC199099
0.7624	Intermediate Similarity	NPC210337
0.7619	Intermediate Similarity	NPC111952
0.7619	Intermediate Similarity	NPC470763
0.7619	Intermediate Similarity	NPC470055
0.7619	Intermediate Similarity	NPC470056
0.7619	Intermediate Similarity	NPC470767
0.7615	Intermediate Similarity	NPC472757
0.7604	Intermediate Similarity	NPC233744
0.76	Intermediate Similarity	NPC180557
0.76	Intermediate Similarity	NPC30677
0.76	Intermediate Similarity	NPC471915
0.76	Intermediate Similarity	NPC473415
0.76	Intermediate Similarity	NPC469329
0.76	Intermediate Similarity	NPC329435
0.76	Intermediate Similarity	NPC37787
0.76	Intermediate Similarity	NPC111273
0.7596	Intermediate Similarity	NPC159533
0.7596	Intermediate Similarity	NPC55954
0.7596	Intermediate Similarity	NPC324001
0.7596	Intermediate Similarity	NPC23584
0.7596	Intermediate Similarity	NPC218513
0.7593	Intermediate Similarity	NPC470076
0.7579	Intermediate Similarity	NPC290731
0.7576	Intermediate Similarity	NPC26046
0.7576	Intermediate Similarity	NPC99653
0.7573	Intermediate Similarity	NPC49532
0.7573	Intermediate Similarity	NPC155974
0.757	Intermediate Similarity	NPC173905
0.757	Intermediate Similarity	NPC284828
0.757	Intermediate Similarity	NPC218853
0.757	Intermediate Similarity	NPC475586
0.757	Intermediate Similarity	NPC472216
0.757	Intermediate Similarity	NPC5475
0.7551	Intermediate Similarity	NPC53890
0.7551	Intermediate Similarity	NPC472642
0.7551	Intermediate Similarity	NPC470832
0.7551	Intermediate Similarity	NPC123252
0.7551	Intermediate Similarity	NPC219937

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 NPC86893 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	2251
0.2-0.3	3740
0.3-0.4	2004
0.4-0.5	620
0.5-0.6	289
0.6-0.7	53
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7573	Intermediate Similarity	NPD5344	Discontinued
0.7345	Intermediate Similarity	NPD7328	Approved
0.7345	Intermediate Similarity	NPD7327	Approved
0.7281	Intermediate Similarity	NPD7516	Approved
0.7248	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7524	Approved
0.7212	Intermediate Similarity	NPD4225	Approved
0.7155	Intermediate Similarity	NPD8296	Approved
0.7155	Intermediate Similarity	NPD8380	Approved
0.7155	Intermediate Similarity	NPD8335	Approved
0.7155	Intermediate Similarity	NPD8379	Approved
0.7155	Intermediate Similarity	NPD8378	Approved
0.7155	Intermediate Similarity	NPD8033	Approved
0.7143	Intermediate Similarity	NPD7640	Approved
0.7143	Intermediate Similarity	NPD6648	Approved
0.7143	Intermediate Similarity	NPD7639	Approved
0.7113	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD8294	Approved
0.7069	Intermediate Similarity	NPD8377	Approved
0.7048	Intermediate Similarity	NPD7638	Approved
0.7027	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6371	Approved
0.701	Intermediate Similarity	NPD6695	Phase 3
0.7009	Intermediate Similarity	NPD7632	Discontinued
0.6961	Remote Similarity	NPD7637	Suspended
0.6909	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7503	Approved
0.6847	Remote Similarity	NPD6686	Approved
0.6786	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7507	Approved
0.6757	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7319	Approved
0.6733	Remote Similarity	NPD7750	Discontinued
0.6701	Remote Similarity	NPD6931	Approved
0.6701	Remote Similarity	NPD7332	Phase 2
0.6701	Remote Similarity	NPD6930	Phase 2
0.6699	Remote Similarity	NPD6698	Approved
0.6699	Remote Similarity	NPD46	Approved
0.6699	Remote Similarity	NPD7838	Discovery
0.6667	Remote Similarity	NPD7115	Discovery
0.6639	Remote Similarity	NPD6319	Approved
0.6635	Remote Similarity	NPD7983	Approved
0.6609	Remote Similarity	NPD8297	Approved
0.6606	Remote Similarity	NPD4159	Approved
0.6598	Remote Similarity	NPD6929	Approved
0.6569	Remote Similarity	NPD4251	Approved
0.6569	Remote Similarity	NPD4250	Approved
0.6552	Remote Similarity	NPD4632	Approved
0.6549	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4822	Approved
0.6531	Remote Similarity	NPD7514	Phase 3
0.6531	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4821	Approved
0.6531	Remote Similarity	NPD4819	Approved
0.6531	Remote Similarity	NPD7525	Registered
0.6531	Remote Similarity	NPD4820	Approved
0.6525	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6675	Approved
0.6518	Remote Similarity	NPD6402	Approved
0.6518	Remote Similarity	NPD7128	Approved
0.6518	Remote Similarity	NPD5739	Approved
0.6491	Remote Similarity	NPD6373	Approved
0.6491	Remote Similarity	NPD6372	Approved
0.6476	Remote Similarity	NPD7087	Discontinued
0.6471	Remote Similarity	NPD4249	Approved
0.6465	Remote Similarity	NPD6898	Phase 1
0.646	Remote Similarity	NPD6412	Phase 2
0.6452	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6399	Phase 3
0.6415	Remote Similarity	NPD5779	Approved
0.6415	Remote Similarity	NPD5778	Approved
0.641	Remote Similarity	NPD8133	Approved
0.6408	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6881	Approved
0.6404	Remote Similarity	NPD6899	Approved
0.6404	Remote Similarity	NPD7320	Approved
0.6392	Remote Similarity	NPD5776	Phase 2
0.6392	Remote Similarity	NPD6925	Approved
0.6381	Remote Similarity	NPD3168	Discontinued
0.6379	Remote Similarity	NPD6650	Approved
0.6379	Remote Similarity	NPD6649	Approved
0.6373	Remote Similarity	NPD6893	Approved
0.6337	Remote Similarity	NPD5362	Discontinued
0.6337	Remote Similarity	NPD7154	Phase 3
0.6327	Remote Similarity	NPD4271	Approved
0.6327	Remote Similarity	NPD4268	Approved
0.6327	Remote Similarity	NPD7145	Approved
0.6325	Remote Similarity	NPD6882	Approved
0.6325	Remote Similarity	NPD6053	Discontinued
0.6316	Remote Similarity	NPD5701	Approved
0.6316	Remote Similarity	NPD5697	Approved
0.63	Remote Similarity	NPD6902	Approved
0.6293	Remote Similarity	NPD7290	Approved
0.6293	Remote Similarity	NPD6883	Approved
0.6293	Remote Similarity	NPD7102	Approved
0.629	Remote Similarity	NPD7492	Approved
0.6289	Remote Similarity	NPD6933	Approved
0.6286	Remote Similarity	NPD6051	Approved
0.6273	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6009	Approved
0.624	Remote Similarity	NPD6616	Approved
0.6239	Remote Similarity	NPD6617	Approved
0.6239	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD8130	Phase 1
0.6239	Remote Similarity	NPD6847	Approved
0.6239	Remote Similarity	NPD6869	Approved
0.623	Remote Similarity	NPD6054	Approved
0.623	Remote Similarity	NPD6059	Approved
0.6228	Remote Similarity	NPD6640	Phase 3
0.6228	Remote Similarity	NPD6008	Approved
0.6224	Remote Similarity	NPD6932	Approved
0.621	Remote Similarity	NPD7604	Phase 2
0.6207	Remote Similarity	NPD6013	Approved
0.6207	Remote Similarity	NPD6012	Approved
0.6207	Remote Similarity	NPD6014	Approved
0.62	Remote Similarity	NPD7509	Discontinued
0.62	Remote Similarity	NPD4748	Discontinued
0.619	Remote Similarity	NPD8293	Discontinued
0.619	Remote Similarity	NPD7078	Approved
0.6182	Remote Similarity	NPD6083	Phase 2
0.6182	Remote Similarity	NPD6084	Phase 2
0.6179	Remote Similarity	NPD8516	Approved
0.6179	Remote Similarity	NPD5983	Phase 2
0.6179	Remote Similarity	NPD8517	Approved
0.6179	Remote Similarity	NPD8515	Approved
0.6179	Remote Similarity	NPD8513	Phase 3
0.6168	Remote Similarity	NPD8034	Phase 2
0.6168	Remote Similarity	NPD8035	Phase 2
0.6162	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD7736	Approved
0.6129	Remote Similarity	NPD6370	Approved
0.6122	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6011	Approved
0.6117	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6336	Discontinued
0.6106	Remote Similarity	NPD5211	Phase 2
0.6106	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7645	Phase 2
0.61	Remote Similarity	NPD6683	Phase 2
0.6082	Remote Similarity	NPD6926	Approved
0.6082	Remote Similarity	NPD6924	Approved
0.608	Remote Similarity	NPD8328	Phase 3
0.6058	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD7748	Approved
0.6048	Remote Similarity	NPD6921	Approved
0.6048	Remote Similarity	NPD6016	Approved
0.6048	Remote Similarity	NPD6015	Approved
0.6036	Remote Similarity	NPD7902	Approved
0.6036	Remote Similarity	NPD4755	Approved
0.602	Remote Similarity	NPD8264	Approved
0.602	Remote Similarity	NPD6942	Approved
0.602	Remote Similarity	NPD7339	Approved
0.6019	Remote Similarity	NPD5332	Approved
0.6019	Remote Similarity	NPD5331	Approved
0.6019	Remote Similarity	NPD6411	Approved
0.6019	Remote Similarity	NPD7515	Phase 2
0.6017	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD6697	Approved
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD6115	Approved
0.6	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6114	Approved
0.6	Remote Similarity	NPD6118	Approved
0.6	Remote Similarity	NPD5988	Approved
0.6	Remote Similarity	NPD5141	Approved
0.6	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD1695	Approved
0.598	Remote Similarity	NPD4790	Discontinued
0.5978	Remote Similarity	NPD371	Approved
0.5963	Remote Similarity	NPD8171	Discontinued
0.5963	Remote Similarity	NPD4202	Approved
0.5962	Remote Similarity	NPD4786	Approved
0.5948	Remote Similarity	NPD5357	Phase 1
0.5938	Remote Similarity	NPD8074	Phase 3
0.5929	Remote Similarity	NPD4700	Approved
0.5929	Remote Similarity	NPD5286	Approved
0.5929	Remote Similarity	NPD5285	Approved
0.5929	Remote Similarity	NPD4696	Approved
0.5926	Remote Similarity	NPD7136	Phase 2
0.5926	Remote Similarity	NPD5785	Approved
0.5922	Remote Similarity	NPD4269	Approved
0.5922	Remote Similarity	NPD6435	Approved
0.5922	Remote Similarity	NPD4270	Approved
0.5922	Remote Similarity	NPD3667	Approved
0.5909	Remote Similarity	NPD5282	Discontinued
0.5902	Remote Similarity	NPD6274	Approved
0.59	Remote Similarity	NPD6116	Phase 1
0.5887	Remote Similarity	NPD7101	Approved
0.5887	Remote Similarity	NPD7100	Approved
0.5882	Remote Similarity	NPD6421	Discontinued
0.5877	Remote Similarity	NPD1700	Approved
0.5865	Remote Similarity	NPD3669	Approved
0.5865	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD7334	Approved
0.5849	Remote Similarity	NPD7521	Approved
0.5849	Remote Similarity	NPD6684	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