NPASS Compound

Structure

CID217091 OpenBabel06191716002D 59 64 0 0 1 0 0 0 0 0999 V2000 -0.7771 3.7220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3864 2.2763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5929 4.8143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9740 0.1611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3647 1.4243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9938 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5306 -0.1175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4530 3.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5498 5.4628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6233 3.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4530 4.4449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5944 5.5344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9655 4.5997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7937 3.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6233 4.9239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0548 4.7429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4258 3.8081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9640 4.9239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1343 4.4449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4247 2.1386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8973 3.2430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8859 0.3961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4357 2.3682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0526 3.2430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5567 2.7553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8906 4.1627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6763 0.8127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1562 1.8624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7937 4.4449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4704 3.8797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5452 2.1110 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4750 3.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0509 1.3973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8973 2.7553 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3046 4.9239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0526 2.7553 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4015 2.5771 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5476 2.0291 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2159 1.6716 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9308 3.0882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1284 1.3355 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8621 0.4456 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4750 2.5114 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0179 1.2286 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5567 3.7133 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0249 4.4451 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5918 0.5303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4312 2.2620 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8972 1.6160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3046 5.8819 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3464 2.2250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8635 1.1497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9754 3.1598 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 1.7270 2.2763 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1038 3.2287 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4631 1.7467 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1888 1.9392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4750 4.4449 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 2 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 41 1 0 0 0 0 7 42 1 0 0 0 0 8 10 2 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 12 16 1 0 0 0 0 13 17 2 0 0 0 0 14 29 2 0 0 0 0 15 29 1 0 0 0 0 16 30 2 0 0 0 0 17 30 1 0 0 0 0 18 19 2 0 0 0 0 18 29 1 0 0 0 0 19 35 1 0 0 0 0 20 31 1 0 0 0 0 20 33 1 0 0 0 0 21 32 1 0 0 0 0 21 34 1 0 0 0 0 22 41 1 0 0 0 0 22 54 1 0 0 0 0 23 53 1 0 0 0 0 24 32 1 0 0 0 0 24 36 1 0 0 0 0 25 45 2 0 0 0 0 25 55 1 0 0 0 0 26 46 2 0 0 0 0 26 56 1 0 0 0 0 27 47 2 0 0 0 0 27 57 1 0 0 0 0 28 48 2 0 0 0 0 28 58 1 0 0 0 0 30 40 1 0 0 0 0 31 37 1 0 0 0 0 31 41 1 6 0 0 0 32 59 1 1 0 0 0 33 42 1 0 0 0 0 33 49 2 0 0 0 0 34 43 1 6 0 0 0 34 55 1 0 0 0 0 35 50 2 0 0 0 0 35 59 1 0 0 0 0 36 37 1 0 0 0 0 36 43 1 6 0 0 0 37 56 1 1 0 0 0 38 39 1 0 0 0 0 38 43 1 1 0 0 0 38 57 1 0 0 0 0 39 44 1 1 0 0 0 39 58 1 0 0 0 0 40 51 2 0 0 0 0 40 53 1 0 0 0 0 41 44 1 6 0 0 0 42 44 1 6 0 0 0 42 54 1 0 0 0 0 43 23 1 6 0 0 0 44 52 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	816.3
Volume:	810.548
LogP:	3.188
LogD:	2.001
LogS:	-4.742
# Rotatable Bonds:	16
TPSA:	204.33
# H-Bond Aceptor:	15
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.156
Synthetic Accessibility Score:	6.548
Fsp3:	0.477
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:	-5.278
MDCK Permeability:	7.580282544950023e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.877
Human Intestinal Absorption (HIA):	0.332
20% Bioavailability (F20%):	0.922
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.297
Plasma Protein Binding (PPB):	70.45209503173828%
Volume Distribution (VD):	1.694
Pgp-substrate:	14.925332069396973%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.015
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.816
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.745
CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.794
CYP3A4-substrate:	0.379

ADMET: Excretion

Clearance (CL):	3.106
Half-life (T1/2):	0.279

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.976
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.367
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.26
Carcinogencity:	0.076
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC217091

Natural Product ID:	NPC217091
*Common Name:**	QSCIDKJZGZYKSP-KCCIQLONSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QSCIDKJZGZYKSP-KCCIQLONSA-N
Standard InCHI:	InChI=1S/C44H48O15/c1-24-32(59-35(50)19-18-29-14-10-8-11-15-29)21-34(55-25(2)45)43(23-53-40(51)30-16-12-9-13-17-30)36(24)37(56-26(3)46)31-20-33(49)42(7)44(52,41(31,6)22-54-42)39(58-28(5)48)38(43)57-27(4)47/h8-19,31-32,34,36-39,52H,1,20-23H2,2-7H3/b19-18+/t31-,32-,34-,36-,37+,38-,39-,41-,42+,43+,44-/m0/s1
SMILES:	O=C(O[C@H]1C[C@H](OC(=O)C)[C@@]2([C@@H](C1=C)[C@H](OC(=O)C)[C@@H]1CC(=O)[C@@]3([C@]([C@H]([C@@H]2OC(=O)C)OC(=O)C)([C@@]1(C)CO3)O)C)COC(=O)c1ccccc1)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL419801
PubChem CID:	15226199
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002967] Hexacarboxylic acids 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
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[11473432]
NPO25366	Sapium indicum	Species	Euphorbiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[12713411]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[14987066]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844936]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974623]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[15974623]
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]
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]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24278	Pistacia chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24373	Lobelia inflata	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24373	Lobelia inflata	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24820	Taxus cuspidata	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]
NPO24852	Helicia nilagirica	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22283	Alhagi maurorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15125.1	Taxus wallichiana var. chinensis	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24278	Pistacia chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24278	Pistacia chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3721	Achyranthes obtusifolia	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25252	Nannocystis exedens	Species	Nannocystaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24882	Erythrophleum chlorostachys	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27390	Vernonia brevifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24730	Lactarius deliciosus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24802	Diploprion bifasciatum	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25277	Seiridium cupressi	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28460	Achyrocline tomentosa	Species	Asteraceae	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]
NPO25389	Allium angulosum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15125.1	Taxus wallichiana var. chinensis	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15482	Vanderbylia fraxinea	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25492	Botryllus leachi	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25441	Desmodium pulchellu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24566	Marasmiellus ramealis	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18706	Anemone thalictroides	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22283	Alhagi maurorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23894	Pulicaria insignis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22152	Tecoma undulata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25466	Lecanora sulphurella	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23994	Ormosia macrophylla	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14189	Osmundaria spiralis	Species	Rhodomelaceae	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]
NPO22618	Psolus eximius	Species	Psolidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25054	Phaleria macrocarpa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24852	Helicia nilagirica	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25311	Guettarda platypoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24461	Clusia sandiensis	Species	Clusiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24278	Pistacia chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24607	Goniothalamus dolichocarpus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24820	Taxus cuspidata	Species	Taxaceae	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]

☑ 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
Others	2

Activity Type	# Activity
Cell Line	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	>	10.0	ug.mL-1	PMID[460967]
NPT2	Others	Unspecified		Control	=	169.0	%	PMID[460967]
NPT2	Others	Unspecified		Control	=	537.0	%	PMID[460967]
NPT27	Others	Unspecified		IC50	>	10.0	ug.mL-1	PMID[460967]

☑ 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 NPC217091 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	345
0.1-0.2	1181
0.2-0.3	2529
0.3-0.4	4772
0.4-0.5	9790
0.5-0.6	11095
0.6-0.7	10695
0.7-0.8	1871
0.8-0.85	184
0.85-0.9	164
0.9-0.95	64
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC472393
0.9795	High Similarity	NPC282239
0.9728	High Similarity	NPC106895
0.966	High Similarity	NPC473670
0.966	High Similarity	NPC21410
0.9597	High Similarity	NPC471102
0.9589	High Similarity	NPC51602
0.9521	High Similarity	NPC112216
0.9521	High Similarity	NPC254558
0.9521	High Similarity	NPC7095
0.9459	High Similarity	NPC242262
0.9459	High Similarity	NPC249471
0.9459	High Similarity	NPC473414
0.9459	High Similarity	NPC472030
0.9459	High Similarity	NPC472005
0.9459	High Similarity	NPC77719
0.9459	High Similarity	NPC472022
0.9459	High Similarity	NPC257213
0.9459	High Similarity	NPC265395
0.9459	High Similarity	NPC237549
0.9459	High Similarity	NPC256142
0.9459	High Similarity	NPC158333
0.9459	High Similarity	NPC304876
0.9459	High Similarity	NPC1173
0.9456	High Similarity	NPC471103
0.9452	High Similarity	NPC60509
0.9452	High Similarity	NPC81698
0.9452	High Similarity	NPC250046
0.9396	High Similarity	NPC228204
0.9396	High Similarity	NPC114410
0.9396	High Similarity	NPC112523
0.9396	High Similarity	NPC26033
0.9396	High Similarity	NPC472549
0.9392	High Similarity	NPC477905
0.9388	High Similarity	NPC165260
0.9388	High Similarity	NPC161239
0.9388	High Similarity	NPC473214
0.9388	High Similarity	NPC470245
0.9388	High Similarity	NPC198455
0.9379	High Similarity	NPC127857
0.9324	High Similarity	NPC306799
0.9324	High Similarity	NPC101043
0.9324	High Similarity	NPC470153
0.932	High Similarity	NPC473215
0.932	High Similarity	NPC476975
0.931	High Similarity	NPC80895
0.931	High Similarity	NPC471912
0.9272	High Similarity	NPC469771
0.9262	High Similarity	NPC472548
0.9247	High Similarity	NPC471107
0.9247	High Similarity	NPC277053
0.9247	High Similarity	NPC301946
0.9247	High Similarity	NPC471100
0.92	High Similarity	NPC219419
0.9184	High Similarity	NPC474935
0.9178	High Similarity	NPC472573
0.9178	High Similarity	NPC95810
0.9178	High Similarity	NPC163719
0.9178	High Similarity	NPC188865
0.9178	High Similarity	NPC472569
0.9178	High Similarity	NPC11685
0.9178	High Similarity	NPC476974
0.9178	High Similarity	NPC25768
0.9178	High Similarity	NPC95265
0.9178	High Similarity	NPC470231
0.9178	High Similarity	NPC57628
0.9178	High Similarity	NPC125106
0.9178	High Similarity	NPC70716
0.9178	High Similarity	NPC472570
0.9139	High Similarity	NPC114357
0.9139	High Similarity	NPC259144
0.9139	High Similarity	NPC155329
0.9116	High Similarity	NPC471104
0.9116	High Similarity	NPC174982
0.9116	High Similarity	NPC472572
0.9116	High Similarity	NPC177940
0.9116	High Similarity	NPC29704
0.9116	High Similarity	NPC476973
0.9116	High Similarity	NPC473088
0.9116	High Similarity	NPC184817
0.9116	High Similarity	NPC158663
0.9116	High Similarity	NPC96903
0.9116	High Similarity	NPC171525
0.9116	High Similarity	NPC472575
0.9116	High Similarity	NPC472568
0.9116	High Similarity	NPC469349
0.9116	High Similarity	NPC470157
0.9116	High Similarity	NPC200471
0.9116	High Similarity	NPC70403
0.9116	High Similarity	NPC470159
0.9116	High Similarity	NPC472571
0.9073	High Similarity	NPC11588
0.9073	High Similarity	NPC229545
0.9073	High Similarity	NPC134685
0.9073	High Similarity	NPC248265
0.9048	High Similarity	NPC470152
0.9048	High Similarity	NPC475759
0.9048	High Similarity	NPC241951
0.9048	High Similarity	NPC475122
0.9041	High Similarity	NPC182869
0.9	High Similarity	NPC91730
0.8993	High Similarity	NPC281717
0.8986	High Similarity	NPC472556
0.898	High Similarity	NPC163087
0.8973	High Similarity	NPC16912
0.894	High Similarity	NPC197037
0.8933	High Similarity	NPC270590
0.8933	High Similarity	NPC301556
0.8933	High Similarity	NPC471101
0.8933	High Similarity	NPC92293
0.8933	High Similarity	NPC266265
0.8917	High Similarity	NPC471493
0.8912	High Similarity	NPC472546
0.891	High Similarity	NPC55744
0.8904	High Similarity	NPC48017
0.8904	High Similarity	NPC43241
0.8904	High Similarity	NPC473758
0.8904	High Similarity	NPC473081
0.8904	High Similarity	NPC473085
0.8904	High Similarity	NPC171207
0.8904	High Similarity	NPC184747
0.8904	High Similarity	NPC473112
0.8904	High Similarity	NPC476094
0.8904	High Similarity	NPC211137
0.8904	High Similarity	NPC200592
0.8904	High Similarity	NPC473613
0.8904	High Similarity	NPC147880
0.8904	High Similarity	NPC473060
0.8904	High Similarity	NPC97667
0.8904	High Similarity	NPC473109
0.8904	High Similarity	NPC4341
0.8896	High Similarity	NPC469417
0.8889	High Similarity	NPC473611
0.8868	High Similarity	NPC102465
0.8867	High Similarity	NPC217918
0.8854	High Similarity	NPC329960
0.8854	High Similarity	NPC66193
0.8854	High Similarity	NPC295408
0.8854	High Similarity	NPC150893
0.8846	High Similarity	NPC476077
0.8844	High Similarity	NPC41481
0.8844	High Similarity	NPC291599
0.8844	High Similarity	NPC97947
0.8844	High Similarity	NPC118080
0.8844	High Similarity	NPC472576
0.8844	High Similarity	NPC224491
0.8844	High Similarity	NPC27377
0.8844	High Similarity	NPC87448
0.8839	High Similarity	NPC469399
0.8836	High Similarity	NPC210591
0.8836	High Similarity	NPC214550
0.8836	High Similarity	NPC475652
0.8812	High Similarity	NPC477471
0.8812	High Similarity	NPC477469
0.8812	High Similarity	NPC477473
0.8812	High Similarity	NPC477466
0.88	High Similarity	NPC475552
0.88	High Similarity	NPC477737
0.8797	High Similarity	NPC471134
0.8784	High Similarity	NPC34012
0.8776	High Similarity	NPC183270
0.8776	High Similarity	NPC100913
0.8776	High Similarity	NPC90614
0.8776	High Similarity	NPC477904
0.8776	High Similarity	NPC275592
0.8767	High Similarity	NPC183122
0.8767	High Similarity	NPC283375
0.8766	High Similarity	NPC473632
0.8766	High Similarity	NPC132599
0.8766	High Similarity	NPC469730
0.8742	High Similarity	NPC61891
0.8725	High Similarity	NPC139067
0.8725	High Similarity	NPC246480
0.8725	High Similarity	NPC147217
0.8725	High Similarity	NPC477894
0.8725	High Similarity	NPC270498
0.8725	High Similarity	NPC473673
0.8725	High Similarity	NPC475429
0.8725	High Similarity	NPC177340
0.8725	High Similarity	NPC191082
0.8716	High Similarity	NPC213567
0.871	High Similarity	NPC11410
0.8684	High Similarity	NPC473403
0.8675	High Similarity	NPC473602
0.8667	High Similarity	NPC51314
0.8667	High Similarity	NPC67777
0.8654	High Similarity	NPC477735
0.8649	High Similarity	NPC472547
0.8645	High Similarity	NPC251139
0.8639	High Similarity	NPC184109
0.8634	High Similarity	NPC469420
0.8634	High Similarity	NPC40138
0.863	High Similarity	NPC195647
0.863	High Similarity	NPC66761
0.863	High Similarity	NPC291638
0.863	High Similarity	NPC17877
0.863	High Similarity	NPC472577
0.86	High Similarity	NPC91703
0.8599	High Similarity	NPC477736
0.859	High Similarity	NPC70344

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 NPC217091 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	765
0.2-0.3	1547
0.3-0.4	2931
0.4-0.5	2285
0.5-0.6	967
0.6-0.7	334
0.7-0.8	34
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8393	Intermediate Similarity	NPD8407	Phase 2
0.8323	Intermediate Similarity	NPD8368	Discontinued
0.8304	Intermediate Similarity	NPD8435	Approved
0.8303	Intermediate Similarity	NPD7799	Discontinued
0.8294	Intermediate Similarity	NPD8434	Phase 2
0.8247	Intermediate Similarity	NPD7236	Approved
0.8198	Intermediate Similarity	NPD8361	Approved
0.8198	Intermediate Similarity	NPD8360	Approved
0.8125	Intermediate Similarity	NPD8485	Approved
0.8101	Intermediate Similarity	NPD7239	Suspended
0.8081	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD8150	Discontinued
0.7651	Intermediate Similarity	NPD7058	Phase 2
0.7651	Intermediate Similarity	NPD7057	Phase 3
0.7582	Intermediate Similarity	NPD7961	Discontinued
0.7566	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7075	Discontinued
0.7455	Intermediate Similarity	NPD6599	Discontinued
0.7435	Intermediate Similarity	NPD8462	Phase 1
0.7391	Intermediate Similarity	NPD6190	Approved
0.734	Intermediate Similarity	NPD8319	Approved
0.734	Intermediate Similarity	NPD8320	Phase 1
0.7321	Intermediate Similarity	NPD7819	Suspended
0.7299	Intermediate Similarity	NPD7473	Discontinued
0.7278	Intermediate Similarity	NPD3817	Phase 2
0.7262	Intermediate Similarity	NPD6801	Discontinued
0.726	Intermediate Similarity	NPD4198	Discontinued
0.7226	Intermediate Similarity	NPD7008	Discontinued
0.7222	Intermediate Similarity	NPD8166	Discontinued
0.7222	Intermediate Similarity	NPD4628	Phase 3
0.7207	Intermediate Similarity	NPD8313	Approved
0.7207	Intermediate Similarity	NPD8312	Approved
0.7204	Intermediate Similarity	NPD7699	Phase 2
0.7204	Intermediate Similarity	NPD7700	Phase 2
0.7198	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7435	Discontinued
0.7195	Intermediate Similarity	NPD6799	Approved
0.7194	Intermediate Similarity	NPD8404	Phase 2
0.7186	Intermediate Similarity	NPD7458	Discontinued
0.7176	Intermediate Similarity	NPD5402	Approved
0.7168	Intermediate Similarity	NPD8127	Discontinued
0.7151	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4380	Phase 2
0.7135	Intermediate Similarity	NPD6535	Approved
0.7135	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6534	Approved
0.7135	Intermediate Similarity	NPD3882	Suspended
0.7126	Intermediate Similarity	NPD6232	Discontinued
0.7119	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5494	Approved
0.7076	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2629	Approved
0.707	Intermediate Similarity	NPD3764	Approved
0.7066	Intermediate Similarity	NPD5403	Approved
0.7062	Intermediate Similarity	NPD7874	Approved
0.7062	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5401	Approved
0.7045	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6166	Phase 2
0.7045	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3787	Discontinued
0.7022	Intermediate Similarity	NPD5844	Phase 1
0.7018	Intermediate Similarity	NPD5760	Phase 2
0.7018	Intermediate Similarity	NPD5761	Phase 2
0.7006	Intermediate Similarity	NPD6273	Approved
0.7	Intermediate Similarity	NPD7411	Suspended
0.7	Intermediate Similarity	NPD6764	Approved
0.7	Intermediate Similarity	NPD6765	Approved
0.6982	Remote Similarity	NPD3226	Approved
0.6966	Remote Similarity	NPD3751	Discontinued
0.6966	Remote Similarity	NPD3818	Discontinued
0.6961	Remote Similarity	NPD7808	Phase 3
0.6961	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD37	Approved
0.6954	Remote Similarity	NPD6234	Discontinued
0.6949	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6782	Approved
0.6947	Remote Similarity	NPD6778	Approved
0.6947	Remote Similarity	NPD6780	Approved
0.6947	Remote Similarity	NPD6777	Approved
0.6947	Remote Similarity	NPD6776	Approved
0.6947	Remote Similarity	NPD6779	Approved
0.6947	Remote Similarity	NPD6781	Approved
0.6946	Remote Similarity	NPD2532	Approved
0.6946	Remote Similarity	NPD2533	Approved
0.6946	Remote Similarity	NPD2534	Approved
0.6936	Remote Similarity	NPD4965	Approved
0.6936	Remote Similarity	NPD4967	Phase 2
0.6936	Remote Similarity	NPD7768	Phase 2
0.6936	Remote Similarity	NPD4966	Approved
0.6933	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7698	Approved
0.6927	Remote Similarity	NPD7696	Phase 3
0.6927	Remote Similarity	NPD7697	Approved
0.6923	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7251	Discontinued
0.6906	Remote Similarity	NPD7685	Pre-registration
0.6897	Remote Similarity	NPD3749	Approved
0.6897	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7870	Phase 2
0.6891	Remote Similarity	NPD7871	Phase 2
0.6887	Remote Similarity	NPD7741	Discontinued
0.6875	Remote Similarity	NPD6959	Discontinued
0.6872	Remote Similarity	NPD7701	Phase 2
0.6872	Remote Similarity	NPD7228	Approved
0.6864	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1934	Approved
0.6853	Remote Similarity	NPD7801	Approved
0.6851	Remote Similarity	NPD6797	Phase 2
0.6848	Remote Similarity	NPD6785	Approved
0.6848	Remote Similarity	NPD6784	Approved
0.6848	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD5951	Approved
0.6846	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7497	Discontinued
0.6832	Remote Similarity	NPD6355	Discontinued
0.6829	Remote Similarity	NPD2346	Discontinued
0.6813	Remote Similarity	NPD6559	Discontinued
0.6807	Remote Similarity	NPD7003	Approved
0.6797	Remote Similarity	NPD5125	Phase 3
0.6797	Remote Similarity	NPD5126	Approved
0.6796	Remote Similarity	NPD7074	Phase 3
0.6768	Remote Similarity	NPD5406	Approved
0.6768	Remote Similarity	NPD5404	Approved
0.6768	Remote Similarity	NPD5408	Approved
0.6768	Remote Similarity	NPD5405	Approved
0.6761	Remote Similarity	NPD919	Approved
0.6753	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD8151	Discontinued
0.6746	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.674	Remote Similarity	NPD7054	Approved
0.6728	Remote Similarity	NPD230	Phase 1
0.6727	Remote Similarity	NPD1471	Phase 3
0.6724	Remote Similarity	NPD2801	Approved
0.6724	Remote Similarity	NPD8455	Phase 2
0.6721	Remote Similarity	NPD7240	Approved
0.6716	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7610	Discontinued
0.6707	Remote Similarity	NPD7305	Phase 1
0.6707	Remote Similarity	NPD2799	Discontinued
0.6703	Remote Similarity	NPD7472	Approved
0.6702	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7095	Approved
0.6686	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7390	Discontinued
0.6686	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7199	Phase 2
0.6684	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2182	Approved
0.6667	Remote Similarity	NPD2796	Approved
0.6646	Remote Similarity	NPD6798	Discontinued
0.6646	Remote Similarity	NPD2313	Discontinued
0.6632	Remote Similarity	NPD6213	Phase 3
0.6632	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6212	Phase 3
0.6629	Remote Similarity	NPD1465	Phase 2
0.6627	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD2067	Discontinued
0.6615	Remote Similarity	NPD6823	Phase 2
0.6611	Remote Similarity	NPD3926	Phase 2
0.6608	Remote Similarity	NPD1512	Approved
0.6607	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3750	Approved
0.6606	Remote Similarity	NPD1510	Phase 2
0.6606	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD6233	Phase 2
0.6603	Remote Similarity	NPD6287	Discontinued
0.66	Remote Similarity	NPD6858	Approved
0.66	Remote Similarity	NPD7094	Approved
0.6592	Remote Similarity	NPD1247	Approved
0.659	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD1549	Phase 2
0.6587	Remote Similarity	NPD970	Clinical (unspecified phase)
0.657	Remote Similarity	NPD920	Approved
0.6568	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD2935	Discontinued
0.6556	Remote Similarity	NPD7229	Phase 3
0.6554	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD2800	Approved
0.6546	Remote Similarity	NPD8285	Discontinued
0.6545	Remote Similarity	NPD7097	Phase 1
0.6541	Remote Similarity	NPD1470	Approved
0.6538	Remote Similarity	NPD8328	Phase 3
0.6533	Remote Similarity	NPD1609	Clinical (unspecified phase)

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