NPASS Compound

Structure

NPC268844 OpenBabel07101719512D 25 26 0 0 1 0 0 0 0 0999 V2000 -6.6776 0.0473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8889 0.6479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4381 1.1633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0913 -0.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9630 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8519 0.6479 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4962 1.3635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1494 -0.2679 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5913 -0.2679 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9259 -1.6679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1986 2.2794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8519 -1.6679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3704 -0.8340 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2567 2.4796 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9630 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8889 -1.6679 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.7357 0.2475 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6755 -0.5655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4444 -2.5019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8430 2.9950 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8148 -1.6679 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3704 -2.5019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9630 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 9 1 0 0 0 0 3 7 2 0 0 0 0 3 17 1 0 0 0 0 4 8 1 0 0 0 0 4 17 1 0 0 0 0 5 10 1 0 0 0 0 5 25 1 0 0 0 0 6 2 1 6 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 11 1 0 0 0 0 8 13 1 6 0 0 0 9 13 1 6 0 0 0 9 18 1 0 0 0 0 10 16 2 3 0 0 0 10 19 1 0 0 0 0 11 14 2 0 0 0 0 11 20 1 0 0 0 0 12 21 2 0 0 0 0 12 22 1 0 0 0 0 13 12 1 1 0 0 0 13 16 1 0 0 0 0 15 25 1 0 0 0 0 23 25 2 0 0 0 0 24 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.11
Volume:	329.773
LogP:	-2.101
LogD:	-0.924
LogS:	-2.027
# Rotatable Bonds:	6
TPSA:	193.12
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	2
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.326
Synthetic Accessibility Score:	4.754
Fsp3:	0.615
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.53
MDCK Permeability:	0.00019360677106305957
Pgp-inhibitor:	0.0
Pgp-substrate:	0.604
Human Intestinal Absorption (HIA):	0.932
20% Bioavailability (F20%):	0.934
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	22.498111724853516%
Volume Distribution (VD):	0.302
Pgp-substrate:	74.62384796142578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.103

ADMET: Excretion

Clearance (CL):	1.769
Half-life (T1/2):	0.616

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.303
Drug-inuced Liver Injury (DILI):	0.636
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.312
Carcinogencity:	0.667
Eye Corrosion:	0.003
Eye Irritation:	0.051
Respiratory Toxicity:	0.868

Download Data

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

Natural Product: NPC268844

Natural Product ID:	NPC268844
*Common Name:**	(-)-Altemicidin
IUPAC Name:	(4aR,6S,7R,7aS)-4-carbamoyl-6-hydroxy-2-methyl-7-[(2-sulfamoylacetyl)amino]-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyridine-7-carboxylic acid
Synonyms:
Standard InCHIKey:	VZRFZUPFQKSXPV-VPFIQFBESA-N
Standard InCHI:	InChI=1S/C13H20N4O7S/c1-17-3-7(11(14)20)6-2-9(18)13(12(21)22,8(6)4-17)16-10(19)5-25(15,23)24/h3,6,8-9,18H,2,4-5H2,1H3,(H2,14,20)(H,16,19)(H,21,22)(H2,15,23,24)/t6-,8+,9-,13+/m0/s1
SMILES:	CN1C=C([C@@H]2C[C@@H]([C@]([C@@H]2C1)(C(=O)O)N=C(CS(=O)(=O)N)O)O)C(=N)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3586273
PubChem CID:	11036174
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0001189] N-acyl-alpha amino acids and derivatives [CHEMONTID:0002402] N-acyl-alpha amino acids [CHEMONTID:0004148] N-acyl-L-alpha-amino acids

*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
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10344559]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10344578]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10348041]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10604756]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10695669]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10724004]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10994816]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11099231]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11132958]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11374972]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11473415]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14738393]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	Australian	n.a.	PMID[15497950]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15813185]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15844966]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15974616]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16180833]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1666120]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16724845]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16830891]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16872146]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17125235]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17315965]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17551212]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17608531]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17844998]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17887721]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17917237]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18044841]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	Indonesian	n.a.	PMID[18081255]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18081255]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18205372]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18327911]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	Northwest Territories, Canada	1995	PMID[18327911]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18666798]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18776684]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19007176]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19129624]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19191549]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19856955]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19883065]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20092333]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20545334]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20836523]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21028889]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21028891]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[21090727]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21314175]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[21639131]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21728289]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	latex	n.a.	PMID[21751787]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21807523]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21873059]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	latex	n.a.	PMID[21879726]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[22145663]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22574670]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22583058]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22591466]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22758660]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22775474]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23387796]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23662937]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24592993]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24754815]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24878306]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24964393]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25211234]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25455147]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25495422]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25537064]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25918793]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25934225]
NPO28613	Streptomyces calvus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26035239]
NPO11450	Pseudoceratina purpurea	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26035239]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26035239]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26465675]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26798949]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26905826]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31013087]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31298537]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31894983]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32298122]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8501018]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[8784423]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8931733]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8982334]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9031666]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9031676]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9066767]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9066768]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9186568]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9531983]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[9711246]
NPO11450	Pseudoceratina purpurea	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28613	Streptomyces calvus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11450	Pseudoceratina purpurea	Species	Pseudoceratinidae	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
LD50	1
Others	2

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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	2120.0	nM	PMID[478040]
NPT32	Organism	Mus musculus	Mus musculus	LD50	=	0.3	mg.kg-1	PMID[478040]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2120.0	nM	PMID[478040]
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	Activity	=	50.0	%	PMID[478040]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	3.0	ug.mL-1	PMID[478040]

☑ 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 NPC268844 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	101
0.1-0.2	1026
0.2-0.3	16732
0.3-0.4	18425
0.4-0.5	6148
0.5-0.6	258
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC314686
0.6304	Remote Similarity	NPC50694
0.6214	Remote Similarity	NPC201968
0.6214	Remote Similarity	NPC209734
0.6058	Remote Similarity	NPC329305
0.5985	Remote Similarity	NPC234542
0.594	Remote Similarity	NPC473224
0.5929	Remote Similarity	NPC76660
0.5929	Remote Similarity	NPC276995
0.5839	Remote Similarity	NPC236644
0.5781	Remote Similarity	NPC193386
0.5772	Remote Similarity	NPC474371
0.5766	Remote Similarity	NPC14537
0.5755	Remote Similarity	NPC15413
0.5725	Remote Similarity	NPC473252
0.5704	Remote Similarity	NPC469466
0.5625	Remote Similarity	NPC471645
0.5608	Remote Similarity	NPC238323

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 NPC268844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	73
0.1-0.2	454
0.2-0.3	3928
0.3-0.4	3859
0.4-0.5	796
0.5-0.6	37
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6148	Remote Similarity	NPD1827	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD1829	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD1828	Approved
0.5899	Remote Similarity	NPD6420	Discontinued
0.5802	Remote Similarity	NPD573	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4228	Discovery
0.5714	Remote Similarity	NPD6413	Approved
0.5669	Remote Similarity	NPD6334	Approved
0.5669	Remote Similarity	NPD6333	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