NPASS Compound

Structure

CID74595 OpenBabel06191715412D 32 36 0 0 1 0 0 0 0 0999 V2000 5.7135 0.3460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1803 0.9340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4468 1.4212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9548 0.5701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0243 1.9117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8700 -1.4514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6429 0.9491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8212 1.4232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1072 -1.4212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6420 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6434 2.8445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8220 2.3709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8209 -0.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2869 -1.8958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8220 -1.4222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6437 -1.8963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4654 -2.3698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7771 0.1974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1069 -0.4732 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6432 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6423 0.9482 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9486 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4643 2.3700 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4649 -0.4736 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4637 1.4218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8214 1.4227 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8217 -0.4741 0.0000 C 0 0 1 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 2.4652 -1.4217 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1702 -3.0039 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3159 2.8610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 9 23 1 0 0 0 0 10 15 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 18 31 2 0 0 0 0 20 19 1 6 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 21 28 1 6 0 0 0 22 26 1 0 0 0 0 22 27 1 1 0 0 0 23 27 1 1 0 0 0 23 29 1 0 0 0 0 24 26 1 0 0 0 0 24 32 1 1 0 0 0 25 30 1 1 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.37
Volume:	496.961
LogP:	5.572
LogD:	5.458
LogS:	-5.629
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.364
Synthetic Accessibility Score:	4.879
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.173
MDCK Permeability:	2.63765159616014e-05
Pgp-inhibitor:	0.038
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.968
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.17
Plasma Protein Binding (PPB):	77.56177520751953%
Volume Distribution (VD):	1.271
Pgp-substrate:	9.26993179321289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.335
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.918
CYP2C9-inhibitor:	0.166
CYP2C9-substrate:	0.246
CYP2D6-inhibitor:	0.685
CYP2D6-substrate:	0.312
CYP3A4-inhibitor:	0.926
CYP3A4-substrate:	0.579

ADMET: Excretion

Clearance (CL):	4.199
Half-life (T1/2):	0.188

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.253
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.131
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.956
Carcinogencity:	0.009
Eye Corrosion:	0.983
Eye Irritation:	0.789
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC74595

Natural Product ID:	NPC74595
*Common Name:**	Betulinaldehyde
IUPAC Name:	(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carbaldehyde
Synonyms:	Betulin Aldehyde; Betulinaldehyde
Standard InCHIKey:	FELCJAPFJOPHSD-ROUWMTJPSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h18,20-25,32H,1,8-17H2,2-7H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1
SMILES:	O=C[C@@]12CC[C@H]([C@@H]2[C@@H]2[C@](CC1)(C)[C@]1(C)CC[C@@H]3[C@]([C@H]1CC2)(C)CC[C@@H](C3(C)C)O)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512622
PubChem CID:	99615
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO14954	Aphelasterias japonica	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978224]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11524125]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11524125]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18341288]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO24136	Melaleuca ericifolia	Species	Myrtaceae	Eukaryota	leaves	Mansoura, Egypt	2006-JAN	PMID[18826277]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22080044]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25050371]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607351]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33170684]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10597	Fructus syzygii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25678	Albertisia papuana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13676	Zanthoxylum brachyacanthum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25678	Albertisia papuana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18010	Lycoperdon pyriforme	Species	Lycoperdaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10597	Fructus syzygii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13676	Zanthoxylum brachyacanthum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23854	Scilla maritima	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25705	Cordia curassavica	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25372	Valeriana fedtschenkoi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16041	Berberis brandisiana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13123	Balanophora harlandii	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19754	Pyracantha coccinea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7333	Fagara cuspidata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18908	Eria robusta	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2161	Strychnos ledermannii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23975	Osteophloeum platyspermum	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17571	Duboscia macrocarpa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO513	Agathosma scaberula	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO245	Euphorbia biglandulosa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21196	Dichotomaria marginata	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17199	Melaleuca genistifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25647	Taraxacum bicorne	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24136	Melaleuca ericifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18010	Lycoperdon pyriforme	Species	Lycoperdaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29226.1	Ficus cordata subsp. salicifolia	Subspecies	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1584	Tolypothrix tjipanasensis	Species	Tolypothrichaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO23854	Scilla maritima	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4074	Lonchocarpus orotinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24446	Diotis maritima	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO22144	Daphne lancifolia	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24416	Artemisia tournefortiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14279.1	Ficus sarmentosa var. thunbergii	Varieties	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25263	Aulacomnium androgynum	Species	Aulacomniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21967	Astragalus asper	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24230	Petriella sordida	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4781	Diospyros discolor	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25678	Albertisia papuana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5771	Sinularia molesta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17549	Polemonium caeruleum	Species	Polemoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24605	Monochaetia compta	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4892	Viburnum davidii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14954	Aphelasterias japonica	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29531	Lupinus cosentinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11048	Ahnfeltia plicata	Species	Ahnfeltiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6157	Dahlstedtia araripensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5064	Derris uliginosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25862	Lafoensia glyptocarpa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25535	Cosmos pringlei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13676	Zanthoxylum brachyacanthum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23698	Gardneria insularis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	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
ED50	1
IC50	2
Others	8

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	4
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	ED50	=	3.3	uM	PMID[537027]
NPT319	Cell Line	B16	Mus musculus	IC50	=	6400.0	nM	PMID[537027]
NPT319	Cell Line	B16	Mus musculus	Activity	=	70.4	%	PMID[537027]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	19400.0	nM	PMID[537026]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	Survival	=	12.0	%	PMID[537028]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	Survival	=	42.0	%	PMID[537028]
NPT27	Others	Unspecified		Survival	=	70.0	%	PMID[537028]
NPT27	Others	Unspecified		Survival	=	80.0	%	PMID[537028]
NPT856	Organism	Semliki forest virus	Semliki forest virus	Activity	=	1.0	%	PMID[537029]
NPT27	Others	Unspecified		Activity	=	0.0	%	PMID[537029]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC=>90	=	25.0	mg/ml	PMID[537030]

☑ 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 NPC74595 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	182
0.1-0.2	1742
0.2-0.3	7979
0.3-0.4	15765
0.4-0.5	6196
0.5-0.6	4586
0.6-0.7	4322
0.7-0.8	1649
0.8-0.85	174
0.85-0.9	64
0.9-0.95	28
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC264665
0.975	High Similarity	NPC269396
0.975	High Similarity	NPC98236
0.962	High Similarity	NPC472743
0.962	High Similarity	NPC475726
0.9512	High Similarity	NPC472739
0.95	High Similarity	NPC474482
0.95	High Similarity	NPC475745
0.9383	High Similarity	NPC292553
0.9383	High Similarity	NPC264317
0.9383	High Similarity	NPC294438
0.9286	High Similarity	NPC169933
0.9268	High Similarity	NPC472738
0.9268	High Similarity	NPC12774
0.9268	High Similarity	NPC2783
0.9259	High Similarity	NPC474233
0.9157	High Similarity	NPC57469
0.9157	High Similarity	NPC4643
0.9157	High Similarity	NPC269360
0.9157	High Similarity	NPC264005
0.9157	High Similarity	NPC33768
0.9136	High Similarity	NPC175410
0.9114	High Similarity	NPC201459
0.9048	High Similarity	NPC16377
0.9048	High Similarity	NPC471900
0.9048	High Similarity	NPC474719
0.8941	High Similarity	NPC213832
0.8941	High Similarity	NPC220498
0.8941	High Similarity	NPC57954
0.8916	High Similarity	NPC76518
0.8889	High Similarity	NPC103754
0.8889	High Similarity	NPC474484
0.8846	High Similarity	NPC178383
0.8846	High Similarity	NPC231256
0.8846	High Similarity	NPC104387
0.8846	High Similarity	NPC212879
0.8846	High Similarity	NPC240235
0.8824	High Similarity	NPC4309
0.881	High Similarity	NPC477579
0.881	High Similarity	NPC235341
0.881	High Similarity	NPC94755
0.881	High Similarity	NPC95594
0.8765	High Similarity	NPC164999
0.8736	High Similarity	NPC475416
0.8734	High Similarity	NPC86305
0.8734	High Similarity	NPC93662
0.8734	High Similarity	NPC14112
0.8734	High Similarity	NPC278091
0.8734	High Similarity	NPC78067
0.8721	High Similarity	NPC247312
0.8721	High Similarity	NPC271974
0.8718	High Similarity	NPC192638
0.8718	High Similarity	NPC62657
0.8718	High Similarity	NPC25511
0.8675	High Similarity	NPC291320
0.8675	High Similarity	NPC471036
0.8659	High Similarity	NPC328264
0.8659	High Similarity	NPC164210
0.8636	High Similarity	NPC287118
0.8636	High Similarity	NPC291373
0.8636	High Similarity	NPC473690
0.8636	High Similarity	NPC224060
0.8636	High Similarity	NPC471902
0.8636	High Similarity	NPC244356
0.8625	High Similarity	NPC202540
0.8625	High Similarity	NPC212241
0.8625	High Similarity	NPC119355
0.8625	High Similarity	NPC248830
0.8608	High Similarity	NPC195155
0.8608	High Similarity	NPC97534
0.8608	High Similarity	NPC174964
0.8605	High Similarity	NPC193360
0.8605	High Similarity	NPC146937
0.8571	High Similarity	NPC146683
0.8571	High Similarity	NPC475509
0.8554	High Similarity	NPC110780
0.8554	High Similarity	NPC145143
0.8554	High Similarity	NPC477858
0.8539	High Similarity	NPC303863
0.8539	High Similarity	NPC277399
0.8523	High Similarity	NPC160506
0.8523	High Similarity	NPC272746
0.8523	High Similarity	NPC471901
0.8519	High Similarity	NPC42853
0.8519	High Similarity	NPC102708
0.8506	High Similarity	NPC122116
0.85	High Similarity	NPC475742
0.85	High Similarity	NPC5767
0.8488	Intermediate Similarity	NPC474684
0.8488	Intermediate Similarity	NPC142361
0.8481	Intermediate Similarity	NPC102313
0.8481	Intermediate Similarity	NPC199316
0.8471	Intermediate Similarity	NPC471034
0.8471	Intermediate Similarity	NPC133954
0.8471	Intermediate Similarity	NPC98270
0.8471	Intermediate Similarity	NPC201655
0.8471	Intermediate Similarity	NPC190704
0.8462	Intermediate Similarity	NPC111234
0.8452	Intermediate Similarity	NPC118800
0.8452	Intermediate Similarity	NPC245866
0.8452	Intermediate Similarity	NPC5280
0.8452	Intermediate Similarity	NPC471037
0.8415	Intermediate Similarity	NPC80297
0.8415	Intermediate Similarity	NPC475727
0.8415	Intermediate Similarity	NPC192744
0.8415	Intermediate Similarity	NPC472742
0.8415	Intermediate Similarity	NPC116119
0.8415	Intermediate Similarity	NPC49627
0.8415	Intermediate Similarity	NPC49599
0.8409	Intermediate Similarity	NPC85173
0.8409	Intermediate Similarity	NPC183283
0.8409	Intermediate Similarity	NPC191684
0.8409	Intermediate Similarity	NPC126993
0.8409	Intermediate Similarity	NPC46758
0.8395	Intermediate Similarity	NPC472746
0.8395	Intermediate Similarity	NPC143133
0.8395	Intermediate Similarity	NPC106078
0.8395	Intermediate Similarity	NPC23884
0.8395	Intermediate Similarity	NPC298168
0.8395	Intermediate Similarity	NPC68828
0.8395	Intermediate Similarity	NPC221420
0.8391	Intermediate Similarity	NPC206060
0.8375	Intermediate Similarity	NPC230704
0.8375	Intermediate Similarity	NPC3403
0.8375	Intermediate Similarity	NPC185536
0.8375	Intermediate Similarity	NPC70982
0.8372	Intermediate Similarity	NPC55309
0.8372	Intermediate Similarity	NPC72133
0.8372	Intermediate Similarity	NPC471737
0.8372	Intermediate Similarity	NPC475862
0.8372	Intermediate Similarity	NPC213412
0.8372	Intermediate Similarity	NPC187545
0.8372	Intermediate Similarity	NPC74363
0.8372	Intermediate Similarity	NPC28252
0.8354	Intermediate Similarity	NPC232112
0.8353	Intermediate Similarity	NPC59453
0.8353	Intermediate Similarity	NPC221758
0.8333	Intermediate Similarity	NPC268040
0.8333	Intermediate Similarity	NPC45296
0.8313	Intermediate Similarity	NPC475679
0.8295	Intermediate Similarity	NPC475921
0.8295	Intermediate Similarity	NPC24772
0.8295	Intermediate Similarity	NPC474704
0.8295	Intermediate Similarity	NPC116146
0.8276	Intermediate Similarity	NPC233836
0.8276	Intermediate Similarity	NPC51700
0.8276	Intermediate Similarity	NPC165895
0.8276	Intermediate Similarity	NPC187376
0.8276	Intermediate Similarity	NPC307426
0.8276	Intermediate Similarity	NPC259009
0.8276	Intermediate Similarity	NPC472497
0.8276	Intermediate Similarity	NPC242468
0.8276	Intermediate Similarity	NPC472495
0.8276	Intermediate Similarity	NPC293564
0.8276	Intermediate Similarity	NPC89747
0.8276	Intermediate Similarity	NPC171203
0.8276	Intermediate Similarity	NPC130577
0.8276	Intermediate Similarity	NPC68160
0.8276	Intermediate Similarity	NPC18064
0.8276	Intermediate Similarity	NPC174619
0.8276	Intermediate Similarity	NPC153604
0.8276	Intermediate Similarity	NPC98442
0.8276	Intermediate Similarity	NPC475740
0.8276	Intermediate Similarity	NPC73064
0.8276	Intermediate Similarity	NPC102683
0.8276	Intermediate Similarity	NPC142415
0.8276	Intermediate Similarity	NPC159046
0.8276	Intermediate Similarity	NPC88716
0.8272	Intermediate Similarity	NPC91573
0.8256	Intermediate Similarity	NPC102292
0.8256	Intermediate Similarity	NPC470574
0.825	Intermediate Similarity	NPC196358
0.825	Intermediate Similarity	NPC472503
0.825	Intermediate Similarity	NPC254509
0.825	Intermediate Similarity	NPC308440
0.825	Intermediate Similarity	NPC5046
0.825	Intermediate Similarity	NPC49168
0.825	Intermediate Similarity	NPC145552
0.8228	Intermediate Similarity	NPC156277
0.8228	Intermediate Similarity	NPC58057
0.8228	Intermediate Similarity	NPC151018
0.8228	Intermediate Similarity	NPC320549
0.8222	Intermediate Similarity	NPC59350
0.8222	Intermediate Similarity	NPC12722
0.8222	Intermediate Similarity	NPC475061
0.8222	Intermediate Similarity	NPC298554
0.8182	Intermediate Similarity	NPC52169
0.8182	Intermediate Similarity	NPC474512
0.8182	Intermediate Similarity	NPC474925
0.8182	Intermediate Similarity	NPC242864
0.8182	Intermediate Similarity	NPC181225
0.8182	Intermediate Similarity	NPC328539
0.8182	Intermediate Similarity	NPC40552
0.8182	Intermediate Similarity	NPC471722
0.8182	Intermediate Similarity	NPC143767
0.8182	Intermediate Similarity	NPC471724
0.8182	Intermediate Similarity	NPC131470
0.8182	Intermediate Similarity	NPC473242
0.8182	Intermediate Similarity	NPC246708
0.8182	Intermediate Similarity	NPC470629

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 NPC74595 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	2205
0.2-0.3	4385
0.3-0.4	1643
0.4-0.5	342
0.5-0.6	143
0.6-0.7	189
0.7-0.8	66
0.8-0.85	6
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9383	High Similarity	NPD7520	Clinical (unspecified phase)
0.8523	High Similarity	NPD8034	Phase 2
0.8523	High Similarity	NPD8035	Phase 2
0.8353	Intermediate Similarity	NPD4786	Approved
0.8295	Intermediate Similarity	NPD5328	Approved
0.8235	Intermediate Similarity	NPD4788	Approved
0.8228	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD3618	Phase 1
0.8118	Intermediate Similarity	NPD3667	Approved
0.8111	Intermediate Similarity	NPD6079	Approved
0.8049	Intermediate Similarity	NPD6117	Approved
0.8025	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD4697	Phase 3
0.7952	Intermediate Similarity	NPD6116	Phase 1
0.7912	Intermediate Similarity	NPD7515	Phase 2
0.7882	Intermediate Similarity	NPD7525	Registered
0.7857	Intermediate Similarity	NPD6114	Approved
0.7857	Intermediate Similarity	NPD6118	Approved
0.7857	Intermediate Similarity	NPD6115	Approved
0.7857	Intermediate Similarity	NPD6697	Approved
0.7826	Intermediate Similarity	NPD4202	Approved
0.7727	Intermediate Similarity	NPD3133	Approved
0.7727	Intermediate Similarity	NPD3666	Approved
0.7727	Intermediate Similarity	NPD3665	Phase 1
0.7711	Intermediate Similarity	NPD3703	Phase 2
0.7654	Intermediate Similarity	NPD4789	Approved
0.7654	Intermediate Similarity	NPD4245	Approved
0.7654	Intermediate Similarity	NPD4244	Approved
0.7625	Intermediate Similarity	NPD5360	Phase 3
0.7625	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD5221	Approved
0.7579	Intermediate Similarity	NPD5222	Approved
0.7579	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7645	Phase 2
0.7553	Intermediate Similarity	NPD7748	Approved
0.7531	Intermediate Similarity	NPD3698	Phase 2
0.75	Intermediate Similarity	NPD6942	Approved
0.75	Intermediate Similarity	NPD5173	Approved
0.75	Intermediate Similarity	NPD7339	Approved
0.75	Intermediate Similarity	NPD4755	Approved
0.7468	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6399	Phase 3
0.7363	Intermediate Similarity	NPD5279	Phase 3
0.7347	Intermediate Similarity	NPD5286	Approved
0.7347	Intermediate Similarity	NPD4700	Approved
0.7347	Intermediate Similarity	NPD4696	Approved
0.7347	Intermediate Similarity	NPD5285	Approved
0.7333	Intermediate Similarity	NPD3668	Phase 3
0.732	Intermediate Similarity	NPD7902	Approved
0.7312	Intermediate Similarity	NPD4753	Phase 2
0.7303	Intermediate Similarity	NPD4221	Approved
0.7303	Intermediate Similarity	NPD4223	Phase 3
0.7273	Intermediate Similarity	NPD5223	Approved
0.7253	Intermediate Similarity	NPD5329	Approved
0.7245	Intermediate Similarity	NPD7638	Approved
0.7241	Intermediate Similarity	NPD3671	Phase 1
0.7209	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5225	Approved
0.72	Intermediate Similarity	NPD5211	Phase 2
0.72	Intermediate Similarity	NPD4633	Approved
0.72	Intermediate Similarity	NPD5224	Approved
0.72	Intermediate Similarity	NPD5226	Approved
0.7172	Intermediate Similarity	NPD7639	Approved
0.7172	Intermediate Similarity	NPD7640	Approved
0.7157	Intermediate Similarity	NPD7128	Approved
0.7157	Intermediate Similarity	NPD5739	Approved
0.7157	Intermediate Similarity	NPD6675	Approved
0.7157	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD4197	Approved
0.7143	Intermediate Similarity	NPD4758	Discontinued
0.7129	Intermediate Similarity	NPD4754	Approved
0.7129	Intermediate Similarity	NPD5175	Approved
0.7129	Intermediate Similarity	NPD5174	Approved
0.7108	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5141	Approved
0.7045	Intermediate Similarity	NPD3617	Approved
0.7019	Intermediate Similarity	NPD6899	Approved
0.7019	Intermediate Similarity	NPD6881	Approved
0.7019	Intermediate Similarity	NPD7320	Approved
0.701	Intermediate Similarity	NPD7900	Approved
0.701	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4768	Approved
0.699	Remote Similarity	NPD4767	Approved
0.6989	Remote Similarity	NPD7521	Approved
0.6989	Remote Similarity	NPD5330	Approved
0.6989	Remote Similarity	NPD5205	Approved
0.6989	Remote Similarity	NPD6409	Approved
0.6989	Remote Similarity	NPD6684	Approved
0.6989	Remote Similarity	NPD4693	Phase 3
0.6989	Remote Similarity	NPD4689	Approved
0.6989	Remote Similarity	NPD7334	Approved
0.6989	Remote Similarity	NPD4138	Approved
0.6989	Remote Similarity	NPD4690	Approved
0.6989	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7146	Approved
0.6989	Remote Similarity	NPD4688	Approved
0.6977	Remote Similarity	NPD6926	Approved
0.6977	Remote Similarity	NPD6924	Approved
0.697	Remote Similarity	NPD6084	Phase 2
0.697	Remote Similarity	NPD6083	Phase 2
0.6952	Remote Similarity	NPD6372	Approved
0.6952	Remote Similarity	NPD6373	Approved
0.6951	Remote Similarity	NPD4224	Phase 2
0.6941	Remote Similarity	NPD6081	Approved
0.6939	Remote Similarity	NPD4629	Approved
0.6939	Remote Similarity	NPD5210	Approved
0.6923	Remote Similarity	NPD5701	Approved
0.6923	Remote Similarity	NPD5697	Approved
0.6887	Remote Similarity	NPD7102	Approved
0.6887	Remote Similarity	NPD7290	Approved
0.6887	Remote Similarity	NPD6883	Approved
0.6857	Remote Similarity	NPD4730	Approved
0.6857	Remote Similarity	NPD5128	Approved
0.6857	Remote Similarity	NPD6011	Approved
0.6857	Remote Similarity	NPD5168	Approved
0.6857	Remote Similarity	NPD4729	Approved
0.6854	Remote Similarity	NPD5364	Discontinued
0.6842	Remote Similarity	NPD5737	Approved
0.6842	Remote Similarity	NPD6903	Approved
0.6842	Remote Similarity	NPD6672	Approved
0.6824	Remote Similarity	NPD4787	Phase 1
0.6822	Remote Similarity	NPD8130	Phase 1
0.6822	Remote Similarity	NPD6617	Approved
0.6822	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6869	Approved
0.6822	Remote Similarity	NPD6650	Approved
0.6822	Remote Similarity	NPD6649	Approved
0.6822	Remote Similarity	NPD6847	Approved
0.6818	Remote Similarity	NPD6933	Approved
0.6813	Remote Similarity	NPD4139	Approved
0.6813	Remote Similarity	NPD4692	Approved
0.6809	Remote Similarity	NPD5690	Phase 2
0.6809	Remote Similarity	NPD4694	Approved
0.6809	Remote Similarity	NPD5280	Approved
0.6792	Remote Similarity	NPD6012	Approved
0.6792	Remote Similarity	NPD6014	Approved
0.6792	Remote Similarity	NPD6013	Approved
0.6759	Remote Similarity	NPD6882	Approved
0.6759	Remote Similarity	NPD8297	Approved
0.6744	Remote Similarity	NPD7152	Approved
0.6744	Remote Similarity	NPD4243	Approved
0.6744	Remote Similarity	NPD7151	Approved
0.6744	Remote Similarity	NPD5777	Approved
0.6744	Remote Similarity	NPD7150	Approved
0.6729	Remote Similarity	NPD5249	Phase 3
0.6729	Remote Similarity	NPD5251	Approved
0.6729	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5247	Approved
0.6729	Remote Similarity	NPD5135	Approved
0.6729	Remote Similarity	NPD5250	Approved
0.6729	Remote Similarity	NPD5169	Approved
0.6729	Remote Similarity	NPD5248	Approved
0.6729	Remote Similarity	NPD4634	Approved
0.6706	Remote Similarity	NPD6923	Approved
0.6706	Remote Similarity	NPD6922	Approved
0.6705	Remote Similarity	NPD3702	Approved
0.6703	Remote Similarity	NPD4748	Discontinued
0.6699	Remote Similarity	NPD7632	Discontinued
0.6697	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD5216	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD5217	Approved
0.6638	Remote Similarity	NPD7507	Approved
0.6632	Remote Similarity	NPD6098	Approved
0.6628	Remote Similarity	NPD7144	Approved
0.6628	Remote Similarity	NPD7143	Approved
0.6628	Remote Similarity	NPD4747	Approved
0.6604	Remote Similarity	NPD6412	Phase 2
0.66	Remote Similarity	NPD5695	Phase 3
0.66	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6929	Approved
0.6593	Remote Similarity	NPD4195	Approved
0.6591	Remote Similarity	NPD4784	Approved
0.6591	Remote Similarity	NPD4785	Approved
0.6577	Remote Similarity	NPD6868	Approved
0.6569	Remote Similarity	NPD5696	Approved
0.6562	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4632	Approved
0.6522	Remote Similarity	NPD4695	Discontinued
0.6522	Remote Similarity	NPD7509	Discontinued
0.6522	Remote Similarity	NPD6931	Approved
0.6522	Remote Similarity	NPD6930	Phase 2
0.6512	Remote Similarity	NPD4137	Phase 3
0.6486	Remote Similarity	NPD5167	Approved
0.6484	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7319	Approved
0.6465	Remote Similarity	NPD5281	Approved
0.6465	Remote Similarity	NPD5284	Approved
0.646	Remote Similarity	NPD6335	Approved
0.6458	Remote Similarity	NPD4623	Approved
0.6458	Remote Similarity	NPD4519	Discontinued
0.6437	Remote Similarity	NPD4691	Approved
0.6429	Remote Similarity	NPD6904	Approved
0.6429	Remote Similarity	NPD6274	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