NPASS Compound

Structure

CID29152 OpenBabel06191715352D 34 38 0 0 1 0 0 0 0 0999 V2000 1.8896 -3.1706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4073 -5.4349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6951 2.9672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6954 -1.9882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6945 1.0113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8021 -3.5760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4995 -2.6465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7583 -3.7786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8470 1.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3887 -0.9769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5412 0.4885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3885 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6942 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8478 -1.4669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8473 -0.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5417 2.4454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5432 -2.4438 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0609 -4.7081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5427 -1.4664 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8478 1.4675 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8473 0.4895 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5415 1.4670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0171 -4.9107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6948 1.9564 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6951 -0.9774 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6948 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8476 0.4890 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5417 3.4234 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4077 1.9666 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3197 -5.8402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6707 -4.1840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 1 0 0 0 0 4 27 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 2 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 17 29 1 0 0 0 0 17 30 1 0 0 0 0 18 26 1 0 0 0 0 18 31 1 0 0 0 0 19 1 1 1 0 0 0 19 21 1 0 0 0 0 20 25 1 0 0 0 0 21 27 1 6 0 0 0 22 26 1 6 0 0 0 22 29 1 0 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 32 2 0 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 26 3 1 6 0 0 0 27 28 1 6 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	511.905
LogP:	5.132
LogD:	4.038
LogS:	-4.174
# Rotatable Bonds:	6
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.44
Synthetic Accessibility Score:	5.63
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.346
MDCK Permeability:	1.4965057744120713e-05
Pgp-inhibitor:	0.353
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.358
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.279
Plasma Protein Binding (PPB):	93.00020599365234%
Volume Distribution (VD):	0.827
Pgp-substrate:	1.5424563884735107%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.552
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.827
CYP2C9-inhibitor:	0.191
CYP2C9-substrate:	0.27
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.244
CYP3A4-inhibitor:	0.638
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	4.498
Half-life (T1/2):	0.801

ADMET: Toxicity

hERG Blockers:	0.091
Human Hepatotoxicity (H-HT):	0.479
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.099
Maximum Recommended Daily Dose:	0.509
Skin Sensitization:	0.958
Carcinogencity:	0.256
Eye Corrosion:	0.031
Eye Irritation:	0.285
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC29152

Natural Product ID:	NPC29152
*Common Name:**	JRQCOSMCTGXCGO-BZAQVUAUSA-N
IUPAC Name:	n.a.
Synonyms:	28-Hydroxymangiferonic Acid
Standard InCHIKey:	JRQCOSMCTGXCGO-BZAQVUAUSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-19(7-6-8-20(2)25(33)34)21-11-13-28(5)23-10-9-22-26(3,18-31)24(32)12-14-29(22)17-30(23,29)16-15-27(21,28)4/h8,19,21-23,31H,6-7,9-18H2,1-5H3,(H,33,34)/b20-8+/t19-,21-,22+,23+,26+,27-,28+,29-,30+/m1/s1
SMILES:	C[C@H](CC/C=C(C)/C(=O)O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4[C@](C)(CO)C(=O)CC[C@]54C[C@@]35CC[C@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL550252
PubChem CID:	45270931
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1246/bcsj.30.618]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757720]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593279]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309313]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17716892]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	China	n.a.	PMID[19278239]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO29381	Trichilia rubescens	Species	Meliaceae	Eukaryota	leaves	Kibale National Park, Uganda	2000-2001	PMID[19299148]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	Ywar Taw village, Shan State of Myanmar	2006-Dec	PMID[19572611]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	South China Sea	n.a.	PMID[25211032]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466882]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31117521]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31873014]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO29344	Parabenzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28805	Thymus piperella	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29400	Conocephalum japonicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26192	Cordylanthus kingii	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29510	Aulacocephalus temmincki	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29446	Stevia polycephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28918	Ophiolepis superba	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29154	Heliotropium floridum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29047	Disynaphia halimifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29292	Teucrium depressum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27269	Annona impressivenia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29415	Hovenia acerba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29189	Castanopsis sclerophylla	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28971	Bersama yangambiensis	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25981	Crinipellis scabella	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29203	Gymnocarpium robertianum	Species	Cystopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3744	Polycephalomyces nipponicus	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13818	Narcissus concolor	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9157	Rubrivivax gelatinosus	Species	n.a.	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28784	Alseodaphne corneri	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29450	Streptomyces parvisporogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29488	Sophora angustifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4244	Doodia picta	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3340	Fridericia chica	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29344	Parabenzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO29142	Kaunia saltensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1245	Eunicella cavolinii	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29068	Papilio phorcas	Species	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28805	Thymus piperella	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29242	Salvia dorrii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28937	Heterotheca grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29127	Cystophora scalaris	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29225	Oncoba echinata	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28845	Eragrostis viscosa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29381	Trichilia rubescens	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28824	Forsteronia refracta	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28898	Grewia mollis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29363	Aconitum nevadense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	CD100	>	100.0	uM	PMID[450341]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	>	100.0	uM	PMID[450341]

☑ 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 NPC29152 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	186
0.1-0.2	1148
0.2-0.3	4965
0.3-0.4	12489
0.4-0.5	9455
0.5-0.6	6530
0.6-0.7	5618
0.7-0.8	2126
0.8-0.85	133
0.85-0.9	39
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9889	High Similarity	NPC156546
0.9667	High Similarity	NPC476174
0.9333	High Similarity	NPC23217
0.9	High Similarity	NPC117122
0.8989	High Similarity	NPC186975
0.8936	High Similarity	NPC114743
0.8936	High Similarity	NPC195366
0.8913	High Similarity	NPC470113
0.8913	High Similarity	NPC476187
0.8901	High Similarity	NPC66344
0.8889	High Similarity	NPC236618
0.8889	High Similarity	NPC96496
0.8876	High Similarity	NPC60350
0.8817	High Similarity	NPC476304
0.8778	High Similarity	NPC70661
0.8764	High Similarity	NPC178025
0.8764	High Similarity	NPC476038
0.8764	High Similarity	NPC181743
0.8764	High Similarity	NPC194937
0.8764	High Similarity	NPC16287
0.8763	High Similarity	NPC472924
0.8737	High Similarity	NPC472941
0.8737	High Similarity	NPC456
0.8723	High Similarity	NPC124207
0.8723	High Similarity	NPC476186
0.871	High Similarity	NPC110923
0.871	High Similarity	NPC74296
0.8696	High Similarity	NPC262043
0.8681	High Similarity	NPC136948
0.8667	High Similarity	NPC283733
0.8632	High Similarity	NPC293052
0.8587	High Similarity	NPC472870
0.8586	High Similarity	NPC312900
0.8571	High Similarity	NPC282524
0.8571	High Similarity	NPC472869
0.8557	High Similarity	NPC166745
0.8557	High Similarity	NPC235464
0.8557	High Similarity	NPC197386
0.8557	High Similarity	NPC98868
0.8556	High Similarity	NPC248758
0.8556	High Similarity	NPC164577
0.8556	High Similarity	NPC19849
0.8556	High Similarity	NPC472864
0.8542	High Similarity	NPC301534
0.8542	High Similarity	NPC250757
0.8511	High Similarity	NPC473998
0.8511	High Similarity	NPC473986
0.8511	High Similarity	NPC474018
0.8495	Intermediate Similarity	NPC473999
0.8495	Intermediate Similarity	NPC309603
0.8495	Intermediate Similarity	NPC214387
0.8495	Intermediate Similarity	NPC474570
0.8478	Intermediate Similarity	NPC93778
0.8478	Intermediate Similarity	NPC476293
0.8469	Intermediate Similarity	NPC470074
0.8469	Intermediate Similarity	NPC287833
0.8462	Intermediate Similarity	NPC201655
0.8462	Intermediate Similarity	NPC29447
0.8462	Intermediate Similarity	NPC471224
0.8454	Intermediate Similarity	NPC253826
0.8444	Intermediate Similarity	NPC97913
0.8444	Intermediate Similarity	NPC215893
0.8438	Intermediate Similarity	NPC318282
0.8438	Intermediate Similarity	NPC173875
0.8438	Intermediate Similarity	NPC469995
0.8438	Intermediate Similarity	NPC174948
0.8421	Intermediate Similarity	NPC474736
0.8421	Intermediate Similarity	NPC474807
0.8404	Intermediate Similarity	NPC51486
0.8404	Intermediate Similarity	NPC477147
0.8404	Intermediate Similarity	NPC48010
0.8404	Intermediate Similarity	NPC477149
0.8352	Intermediate Similarity	NPC85774
0.8352	Intermediate Similarity	NPC214043
0.8352	Intermediate Similarity	NPC165064
0.8352	Intermediate Similarity	NPC472865
0.8351	Intermediate Similarity	NPC328371
0.8351	Intermediate Similarity	NPC327788
0.8333	Intermediate Similarity	NPC8993
0.8333	Intermediate Similarity	NPC91034
0.8333	Intermediate Similarity	NPC477858
0.8333	Intermediate Similarity	NPC472925
0.8333	Intermediate Similarity	NPC472239
0.8333	Intermediate Similarity	NPC320514
0.8317	Intermediate Similarity	NPC201763
0.8316	Intermediate Similarity	NPC475806
0.8316	Intermediate Similarity	NPC204341
0.83	Intermediate Similarity	NPC293753
0.8298	Intermediate Similarity	NPC477973
0.8298	Intermediate Similarity	NPC146554
0.8298	Intermediate Similarity	NPC472240
0.8298	Intermediate Similarity	NPC262858
0.8298	Intermediate Similarity	NPC281524
0.8283	Intermediate Similarity	NPC477521
0.8283	Intermediate Similarity	NPC201406
0.8283	Intermediate Similarity	NPC51370
0.8283	Intermediate Similarity	NPC476274
0.828	Intermediate Similarity	NPC128644
0.828	Intermediate Similarity	NPC158141
0.828	Intermediate Similarity	NPC173089
0.8265	Intermediate Similarity	NPC320306
0.8265	Intermediate Similarity	NPC475894
0.8265	Intermediate Similarity	NPC108078
0.8265	Intermediate Similarity	NPC107243
0.8261	Intermediate Similarity	NPC474083
0.8261	Intermediate Similarity	NPC269638
0.8261	Intermediate Similarity	NPC469948
0.8252	Intermediate Similarity	NPC220155
0.8247	Intermediate Similarity	NPC33473
0.8247	Intermediate Similarity	NPC88310
0.8242	Intermediate Similarity	NPC472740
0.8242	Intermediate Similarity	NPC477373
0.8235	Intermediate Similarity	NPC189863
0.8229	Intermediate Similarity	NPC12722
0.8229	Intermediate Similarity	NPC472930
0.8229	Intermediate Similarity	NPC472871
0.8222	Intermediate Similarity	NPC147066
0.8222	Intermediate Similarity	NPC477372
0.8222	Intermediate Similarity	NPC278459
0.8218	Intermediate Similarity	NPC72151
0.8218	Intermediate Similarity	NPC112009
0.8218	Intermediate Similarity	NPC95899
0.8218	Intermediate Similarity	NPC476237
0.8218	Intermediate Similarity	NPC475050
0.8211	Intermediate Similarity	NPC472866
0.8211	Intermediate Similarity	NPC126993
0.8208	Intermediate Similarity	NPC122056
0.8202	Intermediate Similarity	NPC158846
0.82	Intermediate Similarity	NPC476240
0.82	Intermediate Similarity	NPC118174
0.82	Intermediate Similarity	NPC224720
0.82	Intermediate Similarity	NPC99411
0.82	Intermediate Similarity	NPC476223
0.8191	Intermediate Similarity	NPC474511
0.8191	Intermediate Similarity	NPC146937
0.8191	Intermediate Similarity	NPC72397
0.8191	Intermediate Similarity	NPC104560
0.8191	Intermediate Similarity	NPC1753
0.819	Intermediate Similarity	NPC474315
0.8182	Intermediate Similarity	NPC57079
0.8182	Intermediate Similarity	NPC108368
0.8182	Intermediate Similarity	NPC471717
0.8173	Intermediate Similarity	NPC475941
0.8173	Intermediate Similarity	NPC474901
0.8172	Intermediate Similarity	NPC475007
0.8172	Intermediate Similarity	NPC322159
0.8172	Intermediate Similarity	NPC145879
0.8172	Intermediate Similarity	NPC474733
0.8172	Intermediate Similarity	NPC474778
0.8172	Intermediate Similarity	NPC155011
0.8172	Intermediate Similarity	NPC474732
0.8172	Intermediate Similarity	NPC194417
0.8172	Intermediate Similarity	NPC31564
0.8172	Intermediate Similarity	NPC469994
0.8163	Intermediate Similarity	NPC471153
0.8163	Intermediate Similarity	NPC235053
0.8152	Intermediate Similarity	NPC473246
0.8152	Intermediate Similarity	NPC476412
0.8152	Intermediate Similarity	NPC237712
0.8144	Intermediate Similarity	NPC469406
0.8144	Intermediate Similarity	NPC299100
0.8144	Intermediate Similarity	NPC184870
0.8137	Intermediate Similarity	NPC235889
0.8132	Intermediate Similarity	NPC142253
0.8132	Intermediate Similarity	NPC472867
0.8132	Intermediate Similarity	NPC3511
0.8125	Intermediate Similarity	NPC472814
0.8125	Intermediate Similarity	NPC272746
0.8125	Intermediate Similarity	NPC177037
0.8125	Intermediate Similarity	NPC154101
0.8119	Intermediate Similarity	NPC195290
0.8119	Intermediate Similarity	NPC271980
0.8119	Intermediate Similarity	NPC234892
0.8119	Intermediate Similarity	NPC136289
0.8119	Intermediate Similarity	NPC320447
0.8119	Intermediate Similarity	NPC193934
0.8119	Intermediate Similarity	NPC204450
0.8111	Intermediate Similarity	NPC472478
0.8111	Intermediate Similarity	NPC45495
0.8105	Intermediate Similarity	NPC2983
0.8105	Intermediate Similarity	NPC475921
0.8105	Intermediate Similarity	NPC31985
0.8105	Intermediate Similarity	NPC310236
0.8105	Intermediate Similarity	NPC477943
0.8105	Intermediate Similarity	NPC472477
0.8105	Intermediate Similarity	NPC474704
0.8105	Intermediate Similarity	NPC123912
0.8105	Intermediate Similarity	NPC174342
0.8105	Intermediate Similarity	NPC128496
0.8105	Intermediate Similarity	NPC472475
0.8105	Intermediate Similarity	NPC5509
0.8105	Intermediate Similarity	NPC1015
0.81	Intermediate Similarity	NPC117685
0.81	Intermediate Similarity	NPC266955
0.81	Intermediate Similarity	NPC471041
0.81	Intermediate Similarity	NPC327431
0.809	Intermediate Similarity	NPC198240
0.809	Intermediate Similarity	NPC239098
0.8085	Intermediate Similarity	NPC317590
0.8085	Intermediate Similarity	NPC475740

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 NPC29152 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1428
0.2-0.3	3828
0.3-0.4	2587
0.4-0.5	651
0.5-0.6	181
0.6-0.7	194
0.7-0.8	128
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8081	Intermediate Similarity	NPD6083	Phase 2
0.8081	Intermediate Similarity	NPD6084	Phase 2
0.8	Intermediate Similarity	NPD5737	Approved
0.8	Intermediate Similarity	NPD6672	Approved
0.7982	Intermediate Similarity	NPD7115	Discovery
0.7957	Intermediate Similarity	NPD3666	Approved
0.7957	Intermediate Similarity	NPD3665	Phase 1
0.7957	Intermediate Similarity	NPD3133	Approved
0.7957	Intermediate Similarity	NPD4786	Approved
0.7938	Intermediate Similarity	NPD7515	Phase 2
0.7938	Intermediate Similarity	NPD6079	Approved
0.7921	Intermediate Similarity	NPD7640	Approved
0.7921	Intermediate Similarity	NPD7639	Approved
0.7917	Intermediate Similarity	NPD4753	Phase 2
0.7917	Intermediate Similarity	NPD5328	Approved
0.7857	Intermediate Similarity	NPD6399	Phase 3
0.7849	Intermediate Similarity	NPD4788	Approved
0.7822	Intermediate Similarity	NPD7638	Approved
0.7812	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD6409	Approved
0.7789	Intermediate Similarity	NPD6684	Approved
0.7789	Intermediate Similarity	NPD7334	Approved
0.7789	Intermediate Similarity	NPD7521	Approved
0.7789	Intermediate Similarity	NPD3618	Phase 1
0.7789	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD5330	Approved
0.7789	Intermediate Similarity	NPD7146	Approved
0.7742	Intermediate Similarity	NPD4223	Phase 3
0.7742	Intermediate Similarity	NPD3667	Approved
0.7742	Intermediate Similarity	NPD4221	Approved
0.77	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD4629	Approved
0.77	Intermediate Similarity	NPD5695	Phase 3
0.77	Intermediate Similarity	NPD5210	Approved
0.7692	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD5363	Approved
0.7684	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD5329	Approved
0.7653	Intermediate Similarity	NPD5785	Approved
0.7647	Intermediate Similarity	NPD5696	Approved
0.7629	Intermediate Similarity	NPD6903	Approved
0.7624	Intermediate Similarity	NPD5221	Approved
0.7624	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD5222	Approved
0.7604	Intermediate Similarity	NPD5279	Phase 3
0.76	Intermediate Similarity	NPD7748	Approved
0.7596	Intermediate Similarity	NPD5211	Phase 2
0.7579	Intermediate Similarity	NPD4197	Approved
0.7576	Intermediate Similarity	NPD5281	Approved
0.7576	Intermediate Similarity	NPD5284	Approved
0.757	Intermediate Similarity	NPD6881	Approved
0.757	Intermediate Similarity	NPD6899	Approved
0.7553	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6904	Approved
0.7551	Intermediate Similarity	NPD6673	Approved
0.7551	Intermediate Similarity	NPD6080	Approved
0.7549	Intermediate Similarity	NPD5173	Approved
0.7547	Intermediate Similarity	NPD5739	Approved
0.7547	Intermediate Similarity	NPD6675	Approved
0.7547	Intermediate Similarity	NPD6402	Approved
0.7547	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD4202	Approved
0.7477	Intermediate Similarity	NPD5697	Approved
0.7453	Intermediate Similarity	NPD5141	Approved
0.7451	Intermediate Similarity	NPD4697	Phase 3
0.7431	Intermediate Similarity	NPD7102	Approved
0.7431	Intermediate Similarity	NPD6883	Approved
0.7431	Intermediate Similarity	NPD7290	Approved
0.7423	Intermediate Similarity	NPD4689	Approved
0.7423	Intermediate Similarity	NPD4623	Approved
0.7423	Intermediate Similarity	NPD5690	Phase 2
0.7423	Intermediate Similarity	NPD4138	Approved
0.7423	Intermediate Similarity	NPD4690	Approved
0.7423	Intermediate Similarity	NPD4519	Discontinued
0.7423	Intermediate Similarity	NPD4688	Approved
0.7423	Intermediate Similarity	NPD4693	Phase 3
0.7423	Intermediate Similarity	NPD5205	Approved
0.7407	Intermediate Similarity	NPD6011	Approved
0.7407	Intermediate Similarity	NPD7320	Approved
0.7404	Intermediate Similarity	NPD6404	Discontinued
0.7404	Intermediate Similarity	NPD5286	Approved
0.7404	Intermediate Similarity	NPD4696	Approved
0.7404	Intermediate Similarity	NPD5285	Approved
0.74	Intermediate Similarity	NPD5693	Phase 1
0.74	Intermediate Similarity	NPD7637	Suspended
0.7379	Intermediate Similarity	NPD7902	Approved
0.7379	Intermediate Similarity	NPD4755	Approved
0.7374	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4270	Approved
0.7368	Intermediate Similarity	NPD4269	Approved
0.7364	Intermediate Similarity	NPD6649	Approved
0.7364	Intermediate Similarity	NPD6847	Approved
0.7364	Intermediate Similarity	NPD8130	Phase 1
0.7364	Intermediate Similarity	NPD6617	Approved
0.7364	Intermediate Similarity	NPD6650	Approved
0.7364	Intermediate Similarity	NPD6869	Approved
0.734	Intermediate Similarity	NPD4695	Discontinued
0.7339	Intermediate Similarity	NPD6373	Approved
0.7339	Intermediate Similarity	NPD6014	Approved
0.7339	Intermediate Similarity	NPD6013	Approved
0.7339	Intermediate Similarity	NPD6012	Approved
0.7339	Intermediate Similarity	NPD6372	Approved
0.7333	Intermediate Similarity	NPD5223	Approved
0.7315	Intermediate Similarity	NPD5701	Approved
0.7312	Intermediate Similarity	NPD3617	Approved
0.7308	Intermediate Similarity	NPD4225	Approved
0.7297	Intermediate Similarity	NPD6882	Approved
0.7297	Intermediate Similarity	NPD8297	Approved
0.7273	Intermediate Similarity	NPD5208	Approved
0.7264	Intermediate Similarity	NPD7632	Discontinued
0.7264	Intermediate Similarity	NPD5226	Approved
0.7264	Intermediate Similarity	NPD5224	Approved
0.7264	Intermediate Similarity	NPD4633	Approved
0.7264	Intermediate Similarity	NPD5225	Approved
0.7255	Intermediate Similarity	NPD6001	Approved
0.7245	Intermediate Similarity	NPD6098	Approved
0.7245	Intermediate Similarity	NPD5280	Approved
0.7245	Intermediate Similarity	NPD4694	Approved
0.7238	Intermediate Similarity	NPD4700	Approved
0.7234	Intermediate Similarity	NPD4195	Approved
0.7228	Intermediate Similarity	NPD8034	Phase 2
0.7228	Intermediate Similarity	NPD6050	Approved
0.7228	Intermediate Similarity	NPD8035	Phase 2
0.7216	Intermediate Similarity	NPD3668	Phase 3
0.7207	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5175	Approved
0.7196	Intermediate Similarity	NPD5174	Approved
0.7158	Intermediate Similarity	NPD4252	Approved
0.7158	Intermediate Similarity	NPD7525	Registered
0.7129	Intermediate Similarity	NPD5692	Phase 3
0.7117	Intermediate Similarity	NPD4634	Approved
0.7115	Intermediate Similarity	NPD7614	Phase 1
0.7113	Intermediate Similarity	NPD5362	Discontinued
0.7111	Intermediate Similarity	NPD4747	Approved
0.7111	Intermediate Similarity	NPD4691	Approved
0.7105	Intermediate Similarity	NPD6868	Approved
0.7097	Intermediate Similarity	NPD6117	Approved
0.7091	Intermediate Similarity	NPD6686	Approved
0.7087	Intermediate Similarity	NPD7900	Approved
0.7087	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4632	Approved
0.7071	Intermediate Similarity	NPD5786	Approved
0.7065	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5694	Approved
0.7037	Intermediate Similarity	NPD4754	Approved
0.7033	Intermediate Similarity	NPD6081	Approved
0.7021	Intermediate Similarity	NPD6116	Phase 1
0.7009	Intermediate Similarity	NPD6319	Approved
0.7	Intermediate Similarity	NPD4137	Phase 3
0.7	Intermediate Similarity	NPD6412	Phase 2
0.699	Remote Similarity	NPD5133	Approved
0.6989	Remote Similarity	NPD6942	Approved
0.6989	Remote Similarity	NPD7339	Approved
0.6983	Remote Similarity	NPD6335	Approved
0.6975	Remote Similarity	NPD7604	Phase 2
0.6964	Remote Similarity	NPD6371	Approved
0.6961	Remote Similarity	NPD5207	Approved
0.6957	Remote Similarity	NPD6274	Approved
0.6947	Remote Similarity	NPD6115	Approved
0.6947	Remote Similarity	NPD6114	Approved
0.6947	Remote Similarity	NPD6697	Approved
0.6947	Remote Similarity	NPD6118	Approved
0.6937	Remote Similarity	NPD4729	Approved
0.6937	Remote Similarity	NPD4730	Approved
0.6937	Remote Similarity	NPD5128	Approved
0.6937	Remote Similarity	NPD5168	Approved
0.6923	Remote Similarity	NPD7101	Approved
0.6923	Remote Similarity	NPD7100	Approved
0.6923	Remote Similarity	NPD4789	Approved
0.6917	Remote Similarity	NPD7492	Approved
0.6909	Remote Similarity	NPD6008	Approved
0.6909	Remote Similarity	NPD4767	Approved
0.6909	Remote Similarity	NPD4768	Approved
0.6907	Remote Similarity	NPD5369	Approved
0.6897	Remote Similarity	NPD6009	Approved
0.6897	Remote Similarity	NPD6317	Approved
0.6893	Remote Similarity	NPD6411	Approved
0.6887	Remote Similarity	NPD5959	Approved
0.6885	Remote Similarity	NPD7736	Approved
0.6882	Remote Similarity	NPD4058	Approved
0.6882	Remote Similarity	NPD5733	Approved
0.6864	Remote Similarity	NPD6054	Approved
0.6863	Remote Similarity	NPD6051	Approved
0.686	Remote Similarity	NPD6616	Approved
0.6854	Remote Similarity	NPD4224	Phase 2
0.6848	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6313	Approved
0.6838	Remote Similarity	NPD6314	Approved
0.6832	Remote Similarity	NPD3573	Approved
0.6829	Remote Similarity	NPD7319	Approved
0.6827	Remote Similarity	NPD5779	Approved
0.6827	Remote Similarity	NPD5778	Approved
0.6814	Remote Similarity	NPD5251	Approved
0.6814	Remote Similarity	NPD5247	Approved
0.6814	Remote Similarity	NPD5135	Approved
0.6814	Remote Similarity	NPD5248	Approved
0.6814	Remote Similarity	NPD5249	Phase 3
0.6814	Remote Similarity	NPD5250	Approved
0.6814	Remote Similarity	NPD5169	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