NPASS Compound

Structure

CID218388 OpenBabel06191716012D 35 40 0 0 1 0 0 0 0 0999 V2000 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 15 2 0 0 0 0 6 16 2 0 0 0 0 7 10 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 11 2 0 0 0 0 9 17 1 0 0 0 0 10 19 1 1 0 0 0 11 20 1 0 0 0 0 11 25 1 0 0 0 0 12 21 1 0 0 0 0 12 26 2 0 0 0 0 13 22 1 0 0 0 0 13 27 2 0 0 0 0 14 23 2 0 0 0 0 14 26 1 0 0 0 0 15 21 1 0 0 0 0 15 30 1 0 0 0 0 16 22 1 0 0 0 0 16 31 1 0 0 0 0 17 19 2 0 0 0 0 17 32 1 0 0 0 0 18 23 1 0 0 0 0 18 33 2 0 0 0 0 19 24 1 0 0 0 0 20 24 2 0 0 0 0 20 27 1 0 0 0 0 21 28 2 0 0 0 0 22 29 2 0 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 25 34 2 0 0 0 0 25 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.11
Volume:	449.435
LogP:	1.783
LogD:	2.523
LogS:	-4.741
# Rotatable Bonds:	2
TPSA:	172.94
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.163
Synthetic Accessibility Score:	3.287
Fsp3:	0.04
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.122
MDCK Permeability:	5.092143055662746e-06
Pgp-inhibitor:	0.019
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.241
20% Bioavailability (F20%):	0.888
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	94.60354614257812%
Volume Distribution (VD):	0.265
Pgp-substrate:	3.4805099964141846%

ADMET: Metabolism

CYP1A2-inhibitor:	0.86
CYP1A2-substrate:	0.248
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.621
CYP2C9-substrate:	0.199
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.392
CYP3A4-inhibitor:	0.105
CYP3A4-substrate:	0.117

ADMET: Excretion

Clearance (CL):	3.101
Half-life (T1/2):	0.763

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.708
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.34
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.836
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.045
Respiratory Toxicity:	0.236

Download Data

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

Natural Product: NPC218388

Natural Product ID:	NPC218388
*Common Name:**	Izumiphenazine B
IUPAC Name:	n.a.
Synonyms:	Izumiphenazine B
Standard InCHIKey:	UOIYCAXBKQXVOD-SNVBAGLBSA-N
Standard InCHI:	InChI=1S/C25H16N4O6/c30-15-5-1-3-12-21(15)28-23-14(26-12)7-10(8-18(23)33)19-17(32)9-11(25(34)35)20-24(19)29-22-13(27-20)4-2-6-16(22)31/h1-6,9-10,30-32H,7-8H2,(H,34,35)/t10-/m1/s1
SMILES:	Oc1cc(C(=O)O)c2c(c1[C@H]1CC(=O)c3c(C1)nc1c(n3)c(O)ccc1)nc1c(n2)cccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651326
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000486] Quinoxalines [CHEMONTID:0000416] Phenazines 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
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.	Northwest Territories, Canada	1995	PMID[18327911]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	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]
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]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	30.0	%	PMID[528811]

☑ 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 NPC218388 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	579
0.1-0.2	3309
0.2-0.3	12444
0.3-0.4	8649
0.4-0.5	13835
0.5-0.6	2556
0.6-0.7	1215
0.7-0.8	105
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8708	High Similarity	NPC227824
0.7885	Intermediate Similarity	NPC250448
0.7661	Intermediate Similarity	NPC144381
0.7611	Intermediate Similarity	NPC314648
0.752	Intermediate Similarity	NPC291609
0.748	Intermediate Similarity	NPC124300
0.7467	Intermediate Similarity	NPC315545
0.7467	Intermediate Similarity	NPC314297
0.746	Intermediate Similarity	NPC310618
0.7455	Intermediate Similarity	NPC474188
0.7424	Intermediate Similarity	NPC313345
0.7424	Intermediate Similarity	NPC315638
0.7424	Intermediate Similarity	NPC313796
0.7424	Intermediate Similarity	NPC314855
0.7393	Intermediate Similarity	NPC132385
0.7385	Intermediate Similarity	NPC243058
0.7371	Intermediate Similarity	NPC314834
0.7366	Intermediate Similarity	NPC132329
0.7366	Intermediate Similarity	NPC207686
0.7364	Intermediate Similarity	NPC314573
0.7352	Intermediate Similarity	NPC203635
0.7349	Intermediate Similarity	NPC160898
0.7348	Intermediate Similarity	NPC279589
0.7341	Intermediate Similarity	NPC473800
0.7327	Intermediate Similarity	NPC256268
0.7321	Intermediate Similarity	NPC45048
0.732	Intermediate Similarity	NPC178858
0.7294	Intermediate Similarity	NPC478083
0.7285	Intermediate Similarity	NPC90415
0.7281	Intermediate Similarity	NPC219848
0.7254	Intermediate Similarity	NPC474701
0.7254	Intermediate Similarity	NPC477112
0.7248	Intermediate Similarity	NPC215837
0.7246	Intermediate Similarity	NPC237740
0.7244	Intermediate Similarity	NPC230403
0.7237	Intermediate Similarity	NPC280714
0.722	Intermediate Similarity	NPC51388
0.7211	Intermediate Similarity	NPC208522
0.7191	Intermediate Similarity	NPC294375
0.7191	Intermediate Similarity	NPC220337
0.7175	Intermediate Similarity	NPC206186
0.7173	Intermediate Similarity	NPC118228
0.7165	Intermediate Similarity	NPC165964
0.716	Intermediate Similarity	NPC53534
0.7149	Intermediate Similarity	NPC94842
0.7126	Intermediate Similarity	NPC270515
0.7126	Intermediate Similarity	NPC329631
0.7104	Intermediate Similarity	NPC74619
0.7097	Intermediate Similarity	NPC182222
0.7094	Intermediate Similarity	NPC244741
0.7092	Intermediate Similarity	NPC148889
0.7078	Intermediate Similarity	NPC229893
0.7076	Intermediate Similarity	NPC309845
0.7074	Intermediate Similarity	NPC141454
0.7071	Intermediate Similarity	NPC322064
0.7061	Intermediate Similarity	NPC152620
0.7057	Intermediate Similarity	NPC473639
0.7042	Intermediate Similarity	NPC293151
0.7042	Intermediate Similarity	NPC27041
0.7042	Intermediate Similarity	NPC469727
0.7039	Intermediate Similarity	NPC165599
0.7034	Intermediate Similarity	NPC325297
0.7032	Intermediate Similarity	NPC303225
0.7025	Intermediate Similarity	NPC276657
0.7021	Intermediate Similarity	NPC283117
0.702	Intermediate Similarity	NPC161801
0.7011	Intermediate Similarity	NPC185197
0.7	Intermediate Similarity	NPC90229
0.6987	Remote Similarity	NPC232225
0.6975	Remote Similarity	NPC9894
0.6971	Remote Similarity	NPC312645
0.6966	Remote Similarity	NPC317572
0.6966	Remote Similarity	NPC476098
0.6964	Remote Similarity	NPC274640
0.6957	Remote Similarity	NPC475844
0.6953	Remote Similarity	NPC470586
0.6949	Remote Similarity	NPC270918
0.6942	Remote Similarity	NPC184408
0.6939	Remote Similarity	NPC322482
0.6938	Remote Similarity	NPC473188
0.6936	Remote Similarity	NPC132539
0.6936	Remote Similarity	NPC472259
0.6932	Remote Similarity	NPC477549
0.6929	Remote Similarity	NPC72905
0.6929	Remote Similarity	NPC473312
0.6923	Remote Similarity	NPC57398
0.6917	Remote Similarity	NPC41501
0.6917	Remote Similarity	NPC89508
0.6911	Remote Similarity	NPC179287
0.6908	Remote Similarity	NPC474688
0.6902	Remote Similarity	NPC142385
0.6901	Remote Similarity	NPC246658
0.688	Remote Similarity	NPC49547
0.6878	Remote Similarity	NPC53344
0.6875	Remote Similarity	NPC244856
0.6873	Remote Similarity	NPC137353
0.687	Remote Similarity	NPC314633
0.6865	Remote Similarity	NPC473187
0.6865	Remote Similarity	NPC57453
0.6861	Remote Similarity	NPC67659
0.6855	Remote Similarity	NPC74575
0.6855	Remote Similarity	NPC478078
0.6846	Remote Similarity	NPC306644
0.6846	Remote Similarity	NPC236424
0.6846	Remote Similarity	NPC31700
0.6844	Remote Similarity	NPC288987
0.6842	Remote Similarity	NPC183805
0.6838	Remote Similarity	NPC15801
0.683	Remote Similarity	NPC478032
0.6829	Remote Similarity	NPC216612
0.6829	Remote Similarity	NPC144452
0.6828	Remote Similarity	NPC194040
0.6824	Remote Similarity	NPC477066
0.682	Remote Similarity	NPC79911
0.6818	Remote Similarity	NPC274842
0.6815	Remote Similarity	NPC470018
0.6813	Remote Similarity	NPC477516
0.6807	Remote Similarity	NPC321428
0.6803	Remote Similarity	NPC174576
0.6797	Remote Similarity	NPC478081
0.6795	Remote Similarity	NPC63971
0.6795	Remote Similarity	NPC91868
0.6794	Remote Similarity	NPC478080
0.679	Remote Similarity	NPC469928
0.6789	Remote Similarity	NPC121069
0.6778	Remote Similarity	NPC39679
0.6777	Remote Similarity	NPC39500
0.6774	Remote Similarity	NPC120798
0.6773	Remote Similarity	NPC260434
0.6767	Remote Similarity	NPC276517
0.6763	Remote Similarity	NPC23294
0.6761	Remote Similarity	NPC220851
0.6757	Remote Similarity	NPC17437
0.6755	Remote Similarity	NPC89549
0.6752	Remote Similarity	NPC474916
0.6748	Remote Similarity	NPC472099
0.6747	Remote Similarity	NPC202503
0.6745	Remote Similarity	NPC101350
0.6745	Remote Similarity	NPC41679
0.6742	Remote Similarity	NPC258048
0.6736	Remote Similarity	NPC472098
0.6734	Remote Similarity	NPC205372
0.6732	Remote Similarity	NPC477067
0.6732	Remote Similarity	NPC478082
0.6729	Remote Similarity	NPC282346
0.6725	Remote Similarity	NPC207620
0.6724	Remote Similarity	NPC45850
0.6723	Remote Similarity	NPC133156
0.6722	Remote Similarity	NPC303951
0.6721	Remote Similarity	NPC152768
0.6721	Remote Similarity	NPC148183
0.6721	Remote Similarity	NPC3207
0.672	Remote Similarity	NPC186351
0.6718	Remote Similarity	NPC469734
0.6708	Remote Similarity	NPC86834
0.6708	Remote Similarity	NPC210828
0.6706	Remote Similarity	NPC470022
0.6706	Remote Similarity	NPC119006
0.6706	Remote Similarity	NPC235685
0.6704	Remote Similarity	NPC209981
0.6702	Remote Similarity	NPC169716
0.6697	Remote Similarity	NPC322644
0.6696	Remote Similarity	NPC471743
0.6694	Remote Similarity	NPC478141
0.6693	Remote Similarity	NPC39370
0.6693	Remote Similarity	NPC97902
0.6692	Remote Similarity	NPC107836
0.6681	Remote Similarity	NPC134848
0.6681	Remote Similarity	NPC200836
0.668	Remote Similarity	NPC200553
0.668	Remote Similarity	NPC279189
0.6679	Remote Similarity	NPC316110
0.6679	Remote Similarity	NPC315893
0.6679	Remote Similarity	NPC101312
0.6679	Remote Similarity	NPC313587
0.6667	Remote Similarity	NPC472116
0.6667	Remote Similarity	NPC470017
0.6667	Remote Similarity	NPC294620
0.6667	Remote Similarity	NPC478045
0.6654	Remote Similarity	NPC100734
0.6654	Remote Similarity	NPC88923
0.6654	Remote Similarity	NPC315634
0.6653	Remote Similarity	NPC5145
0.6653	Remote Similarity	NPC477110
0.6653	Remote Similarity	NPC330009
0.6653	Remote Similarity	NPC280799
0.6652	Remote Similarity	NPC95898
0.6641	Remote Similarity	NPC6786
0.6641	Remote Similarity	NPC472061
0.664	Remote Similarity	NPC208084
0.664	Remote Similarity	NPC473179
0.6639	Remote Similarity	NPC211813
0.6639	Remote Similarity	NPC328318
0.6639	Remote Similarity	NPC328596
0.6639	Remote Similarity	NPC477111
0.6639	Remote Similarity	NPC317752
0.6629	Remote Similarity	NPC244543
0.6628	Remote Similarity	NPC210296
0.6626	Remote Similarity	NPC87413
0.6616	Remote Similarity	NPC67401

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 NPC218388 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	677
0.2-0.3	1146
0.3-0.4	2072
0.4-0.5	2917
0.5-0.6	1588
0.6-0.7	394
0.7-0.8	16
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
0.7893	Intermediate Similarity	NPD5488	Discontinued
0.7583	Intermediate Similarity	NPD3746	Discontinued
0.7302	Intermediate Similarity	NPD3986	Discontinued
0.7246	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6456	Discontinued
0.7155	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5416	Discontinued
0.7097	Intermediate Similarity	NPD2951	Discontinued
0.7083	Intermediate Similarity	NPD7395	Discontinued
0.7075	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD5482	Discontinued
0.7029	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8091	Phase 3
0.6992	Remote Similarity	NPD2916	Discontinued
0.698	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.695	Remote Similarity	NPD8463	Approved
0.6929	Remote Similarity	NPD6716	Phase 1
0.6923	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1505	Phase 2
0.6907	Remote Similarity	NPD5530	Phase 1
0.6905	Remote Similarity	NPD4368	Phase 2
0.689	Remote Similarity	NPD7417	Discontinued
0.6887	Remote Similarity	NPD7996	Phase 2
0.6883	Remote Similarity	NPD7603	Discontinued
0.6872	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7925	Phase 2
0.6854	Remote Similarity	NPD7924	Phase 2
0.6853	Remote Similarity	NPD4373	Phase 2
0.685	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3959	Phase 2
0.6809	Remote Similarity	NPD3962	Phase 2
0.68	Remote Similarity	NPD4952	Phase 3
0.6787	Remote Similarity	NPD4845	Discontinued
0.6784	Remote Similarity	NPD4561	Discontinued
0.6773	Remote Similarity	NPD6962	Phase 2
0.6772	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD3809	Discontinued
0.6757	Remote Similarity	NPD8358	Approved
0.6752	Remote Similarity	NPD7181	Phase 3
0.6746	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7921	Approved
0.6741	Remote Similarity	NPD6159	Phase 2
0.6736	Remote Similarity	NPD5429	Discontinued
0.6732	Remote Similarity	NPD7853	Phase 2
0.6725	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.672	Remote Similarity	NPD3259	Approved
0.672	Remote Similarity	NPD8430	Approved
0.6716	Remote Similarity	NPD5450	Discontinued
0.6708	Remote Similarity	NPD3243	Approved
0.6707	Remote Similarity	NPD3925	Approved
0.6696	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD8356	Approved
0.6692	Remote Similarity	NPD7923	Phase 2
0.6667	Remote Similarity	NPD7301	Phase 3
0.6667	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4429	Discontinued
0.6655	Remote Similarity	NPD8349	Phase 1
0.6654	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD7803	Approved
0.6652	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.664	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.664	Remote Similarity	NPD1867	Approved
0.664	Remote Similarity	NPD3258	Approved
0.6639	Remote Similarity	NPD6376	Discontinued
0.6628	Remote Similarity	NPD6790	Phase 1
0.6626	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD3263	Phase 3
0.6614	Remote Similarity	NPD7426	Phase 1
0.6586	Remote Similarity	NPD7726	Phase 1
0.6567	Remote Similarity	NPD6228	Discontinued
0.6546	Remote Similarity	NPD5850	Phase 3
0.6537	Remote Similarity	NPD5891	Approved
0.6535	Remote Similarity	NPD5022	Discontinued
0.6535	Remote Similarity	NPD5479	Discontinued
0.6525	Remote Similarity	NPD5512	Phase 3
0.652	Remote Similarity	NPD8363	Approved
0.652	Remote Similarity	NPD5507	Approved
0.652	Remote Similarity	NPD8364	Approved
0.652	Remote Similarity	NPD5506	Approved
0.6517	Remote Similarity	NPD8244	Phase 2
0.6516	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD1294	Discontinued
0.6515	Remote Similarity	NPD6987	Phase 1
0.651	Remote Similarity	NPD1467	Approved
0.651	Remote Similarity	NPD1466	Phase 3
0.6507	Remote Similarity	NPD7867	Phase 1
0.6506	Remote Similarity	NPD6531	Approved
0.6506	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4312	Approved
0.6506	Remote Similarity	NPD7404	Approved
0.6506	Remote Similarity	NPD6530	Approved
0.6506	Remote Similarity	NPD7708	Approved
0.65	Remote Similarity	NPD2779	Approved
0.6492	Remote Similarity	NPD5164	Discontinued
0.649	Remote Similarity	NPD5936	Approved
0.649	Remote Similarity	NPD5939	Approved
0.6483	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD3257	Approved
0.6477	Remote Similarity	NPD8102	Discontinued
0.6473	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD7955	Approved
0.6468	Remote Similarity	NPD7956	Approved
0.6461	Remote Similarity	NPD6290	Phase 2
0.6457	Remote Similarity	NPD7994	Phase 2
0.6453	Remote Similarity	NPD5316	Approved
0.6446	Remote Similarity	NPD8114	Approved
0.6446	Remote Similarity	NPD8115	Approved
0.6444	Remote Similarity	NPD2177	Approved
0.6444	Remote Similarity	NPD2176	Approved
0.6444	Remote Similarity	NPD2175	Phase 3
0.6443	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD8370	Discontinued
0.6442	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD4948	Discontinued
0.6434	Remote Similarity	NPD6142	Phase 3
0.6434	Remote Similarity	NPD4894	Discontinued
0.6432	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6431	Remote Similarity	NPD7767	Approved
0.6429	Remote Similarity	NPD6209	Approved
0.6429	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD2336	Approved
0.6417	Remote Similarity	NPD484	Approved
0.6414	Remote Similarity	NPD8310	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD4897	Phase 2
0.6403	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD5197	Approved
0.6402	Remote Similarity	NPD5196	Approved
0.6402	Remote Similarity	NPD5194	Approved
0.64	Remote Similarity	NPD7293	Approved
0.6397	Remote Similarity	NPD5866	Approved
0.6392	Remote Similarity	NPD4328	Approved
0.6392	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD5445	Approved
0.6391	Remote Similarity	NPD8101	Phase 3
0.6387	Remote Similarity	NPD6722	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD8357	Approved
0.638	Remote Similarity	NPD8466	Approved
0.638	Remote Similarity	NPD8465	Approved
0.638	Remote Similarity	NPD8467	Approved
0.6377	Remote Similarity	NPD3328	Phase 2
0.6375	Remote Similarity	NPD2778	Approved
0.6373	Remote Similarity	NPD1955	Discontinued
0.637	Remote Similarity	NPD5050	Approved
0.6356	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD4502	Phase 2
0.6353	Remote Similarity	NPD8289	Discontinued
0.6352	Remote Similarity	NPD2762	Phase 2
0.635	Remote Similarity	NPD1483	Discontinued
0.6349	Remote Similarity	NPD7180	Phase 3
0.6346	Remote Similarity	NPD3006	Discontinued
0.6339	Remote Similarity	NPD6752	Phase 1
0.6339	Remote Similarity	NPD6753	Phase 1
0.6336	Remote Similarity	NPD8016	Phase 3
0.6336	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD7878	Phase 2
0.6335	Remote Similarity	NPD5632	Approved
0.6335	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD8096	Phase 3
0.6331	Remote Similarity	NPD8097	Phase 3
0.633	Remote Similarity	NPD7588	Discontinued
0.6327	Remote Similarity	NPD7222	Phase 2
0.6324	Remote Similarity	NPD7556	Discontinued
0.632	Remote Similarity	NPD6733	Discontinued
0.632	Remote Similarity	NPD6452	Discontinued
0.6318	Remote Similarity	NPD2307	Discontinued
0.6314	Remote Similarity	NPD5928	Phase 1
0.6311	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD5608	Approved
0.6307	Remote Similarity	NPD5609	Approved
0.6305	Remote Similarity	NPD3945	Discontinued
0.6304	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7665	Phase 2
0.6301	Remote Similarity	NPD7302	Phase 3
0.6301	Remote Similarity	NPD7300	Phase 3
0.6301	Remote Similarity	NPD7666	Phase 3
0.6299	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD1572	Phase 2
0.6292	Remote Similarity	NPD4558	Phase 2
0.629	Remote Similarity	NPD8426	Approved
0.629	Remote Similarity	NPD8425	Approved
0.629	Remote Similarity	NPD8459	Approved
0.629	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.629	Remote Similarity	NPD8460	Approved
0.6288	Remote Similarity	NPD5821	Approved
0.6286	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6285	Remote Similarity	NPD5930	Phase 3
0.6282	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD8100	Phase 3

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