NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	214.14
Volume:	246.491
LogP:	3.761
LogD:	3.623
LogS:	-4.727
# Rotatable Bonds:	2
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.799
Synthetic Accessibility Score:	2.99
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.388
MDCK Permeability:	1.6619200323475525e-05
Pgp-inhibitor:	0.493
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.982
Plasma Protein Binding (PPB):	93.265380859375%
Volume Distribution (VD):	1.213
Pgp-substrate:	6.0026655197143555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.832
CYP1A2-substrate:	0.913
CYP2C19-inhibitor:	0.566
CYP2C19-substrate:	0.499
CYP2C9-inhibitor:	0.678
CYP2C9-substrate:	0.22
CYP2D6-inhibitor:	0.807
CYP2D6-substrate:	0.243
CYP3A4-inhibitor:	0.47
CYP3A4-substrate:	0.383

ADMET: Excretion

Clearance (CL):	8.373
Half-life (T1/2):	0.556

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.116
Drug-inuced Liver Injury (DILI):	0.54
AMES Toxicity:	0.191
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.782
Carcinogencity:	0.325
Eye Corrosion:	0.038
Eye Irritation:	0.967
Respiratory Toxicity:	0.144

Download Data

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

Natural Product: NPC314690

Natural Product ID:	NPC314690
*Common Name:**	Anmindenol A
IUPAC Name:	[(3E)-5-methyl-3-(2-methylpropylidene)inden-1-yl]methanol
Synonyms:
Standard InCHIKey:	RYMVRCNUFQDGOQ-WUXMJOGZSA-N
Standard InCHI:	InChI=1S/C15H18O/c1-10(2)6-12-8-13(9-16)14-5-4-11(3)7-15(12)14/h4-8,10,16H,9H2,1-3H3/b12-6+
SMILES:	CC(C)/C=C/1C=C(CO)c2ccc(C)cc12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3298067
PubChem CID:	90682923
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000021] Indenes and isoindenes

*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.	n.a.	n.a.	PMID[18081255]
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[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]
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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	23000.0	nM	PMID[491764]

☑ 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 NPC314690 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	197
0.1-0.2	1287
0.2-0.3	3226
0.3-0.4	12901
0.4-0.5	15634
0.5-0.6	7558
0.6-0.7	1580
0.7-0.8	271
0.8-0.85	30
0.85-0.9	10
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8842	High Similarity	NPC289117
0.8791	High Similarity	NPC79917
0.8763	High Similarity	NPC315794
0.8673	High Similarity	NPC471133
0.8652	High Similarity	NPC93843
0.8523	High Similarity	NPC172984
0.8495	Intermediate Similarity	NPC128645
0.8372	Intermediate Similarity	NPC224544
0.837	Intermediate Similarity	NPC1793
0.837	Intermediate Similarity	NPC199567
0.8283	Intermediate Similarity	NPC19856
0.8265	Intermediate Similarity	NPC469481
0.8222	Intermediate Similarity	NPC304538
0.82	Intermediate Similarity	NPC56168
0.8191	Intermediate Similarity	NPC220596
0.8132	Intermediate Similarity	NPC474354
0.8119	Intermediate Similarity	NPC243601
0.8043	Intermediate Similarity	NPC474211
0.8041	Intermediate Similarity	NPC21959
0.8022	Intermediate Similarity	NPC168855
0.8	Intermediate Similarity	NPC87299
0.8	Intermediate Similarity	NPC329319
0.8	Intermediate Similarity	NPC99394
0.8	Intermediate Similarity	NPC103326
0.7961	Intermediate Similarity	NPC27252
0.7961	Intermediate Similarity	NPC472980
0.7961	Intermediate Similarity	NPC472979
0.7907	Intermediate Similarity	NPC108218
0.79	Intermediate Similarity	NPC245927
0.7889	Intermediate Similarity	NPC133050
0.7889	Intermediate Similarity	NPC242628
0.7889	Intermediate Similarity	NPC117180
0.7885	Intermediate Similarity	NPC64642
0.7885	Intermediate Similarity	NPC472982
0.7885	Intermediate Similarity	NPC149455
0.7864	Intermediate Similarity	NPC83409
0.7864	Intermediate Similarity	NPC185763
0.7849	Intermediate Similarity	NPC243166
0.7841	Intermediate Similarity	NPC66655
0.7798	Intermediate Similarity	NPC472862
0.7778	Intermediate Similarity	NPC324602
0.7736	Intermediate Similarity	NPC133308
0.7685	Intermediate Similarity	NPC169616
0.7674	Intermediate Similarity	NPC208302
0.767	Intermediate Similarity	NPC472221
0.767	Intermediate Similarity	NPC472222
0.7664	Intermediate Similarity	NPC471188
0.7664	Intermediate Similarity	NPC111108
0.7619	Intermediate Similarity	NPC112903
0.7614	Intermediate Similarity	NPC189371
0.7609	Intermediate Similarity	NPC475199
0.7609	Intermediate Similarity	NPC283012
0.7596	Intermediate Similarity	NPC471186
0.757	Intermediate Similarity	NPC132720
0.7553	Intermediate Similarity	NPC99482
0.7524	Intermediate Similarity	NPC94751
0.7524	Intermediate Similarity	NPC142326
0.75	Intermediate Similarity	NPC475225
0.7473	Intermediate Similarity	NPC469894
0.7451	Intermediate Similarity	NPC128723
0.7447	Intermediate Similarity	NPC267704
0.7434	Intermediate Similarity	NPC238582
0.7431	Intermediate Similarity	NPC302371
0.7429	Intermediate Similarity	NPC117115
0.7404	Intermediate Similarity	NPC235762
0.7404	Intermediate Similarity	NPC471228
0.74	Intermediate Similarity	NPC289769
0.7391	Intermediate Similarity	NPC328178
0.7391	Intermediate Similarity	NPC164449
0.7391	Intermediate Similarity	NPC184030
0.7387	Intermediate Similarity	NPC469719
0.7383	Intermediate Similarity	NPC64586
0.7368	Intermediate Similarity	NPC133302
0.7358	Intermediate Similarity	NPC21594
0.7358	Intermediate Similarity	NPC37914
0.7353	Intermediate Similarity	NPC77492
0.7353	Intermediate Similarity	NPC6597
0.7353	Intermediate Similarity	NPC79241
0.7347	Intermediate Similarity	NPC274455
0.7347	Intermediate Similarity	NPC70940
0.7347	Intermediate Similarity	NPC26224
0.7347	Intermediate Similarity	NPC86670
0.7333	Intermediate Similarity	NPC238696
0.7327	Intermediate Similarity	NPC8392
0.7326	Intermediate Similarity	NPC82770
0.7326	Intermediate Similarity	NPC78954
0.7326	Intermediate Similarity	NPC239931
0.7321	Intermediate Similarity	NPC137496
0.7321	Intermediate Similarity	NPC154511
0.7321	Intermediate Similarity	NPC247858
0.7321	Intermediate Similarity	NPC474358
0.7321	Intermediate Similarity	NPC212891
0.7321	Intermediate Similarity	NPC257540
0.7321	Intermediate Similarity	NPC474387
0.7321	Intermediate Similarity	NPC92
0.7321	Intermediate Similarity	NPC469663
0.7315	Intermediate Similarity	NPC58865
0.7308	Intermediate Similarity	NPC154905
0.7308	Intermediate Similarity	NPC60373
0.7297	Intermediate Similarity	NPC274839
0.729	Intermediate Similarity	NPC151477
0.729	Intermediate Similarity	NPC66834
0.7257	Intermediate Similarity	NPC477136
0.7255	Intermediate Similarity	NPC312132
0.7255	Intermediate Similarity	NPC259512
0.7248	Intermediate Similarity	NPC95126
0.7248	Intermediate Similarity	NPC475002
0.7248	Intermediate Similarity	NPC474057
0.7241	Intermediate Similarity	NPC18785
0.7234	Intermediate Similarity	NPC73637
0.7234	Intermediate Similarity	NPC106313
0.7234	Intermediate Similarity	NPC121478
0.7232	Intermediate Similarity	NPC192948
0.7232	Intermediate Similarity	NPC35797
0.7217	Intermediate Similarity	NPC146673
0.7217	Intermediate Similarity	NPC233923
0.7216	Intermediate Similarity	NPC211237
0.7212	Intermediate Similarity	NPC174911
0.7212	Intermediate Similarity	NPC211885
0.7212	Intermediate Similarity	NPC264728
0.7212	Intermediate Similarity	NPC72729
0.7209	Intermediate Similarity	NPC6107
0.72	Intermediate Similarity	NPC304541
0.7193	Intermediate Similarity	NPC164649
0.7193	Intermediate Similarity	NPC48342
0.7191	Intermediate Similarity	NPC54269
0.7184	Intermediate Similarity	NPC474073
0.7184	Intermediate Similarity	NPC120393
0.7182	Intermediate Similarity	NPC322753
0.7182	Intermediate Similarity	NPC66208
0.7182	Intermediate Similarity	NPC471189
0.7172	Intermediate Similarity	NPC258219
0.7172	Intermediate Similarity	NPC123273
0.7172	Intermediate Similarity	NPC318325
0.7172	Intermediate Similarity	NPC242240
0.717	Intermediate Similarity	NPC272029
0.7168	Intermediate Similarity	NPC242764
0.7168	Intermediate Similarity	NPC38893
0.7168	Intermediate Similarity	NPC105141
0.7168	Intermediate Similarity	NPC308311
0.7168	Intermediate Similarity	NPC219112
0.7168	Intermediate Similarity	NPC477137
0.7157	Intermediate Similarity	NPC222146
0.7157	Intermediate Similarity	NPC469893
0.7157	Intermediate Similarity	NPC144682
0.7143	Intermediate Similarity	NPC51015
0.7143	Intermediate Similarity	NPC476357
0.7143	Intermediate Similarity	NPC268160
0.713	Intermediate Similarity	NPC151197
0.7129	Intermediate Similarity	NPC325292
0.7129	Intermediate Similarity	NPC138117
0.7117	Intermediate Similarity	NPC287055
0.7117	Intermediate Similarity	NPC206414
0.7117	Intermediate Similarity	NPC306977
0.7117	Intermediate Similarity	NPC250323
0.7117	Intermediate Similarity	NPC242957
0.7117	Intermediate Similarity	NPC228425
0.7115	Intermediate Similarity	NPC252821
0.7115	Intermediate Similarity	NPC33675
0.7115	Intermediate Similarity	NPC299762
0.7115	Intermediate Similarity	NPC122005
0.7105	Intermediate Similarity	NPC304510
0.7105	Intermediate Similarity	NPC172219
0.71	Intermediate Similarity	NPC300017
0.7093	Intermediate Similarity	NPC289915
0.7093	Intermediate Similarity	NPC113837
0.7087	Intermediate Similarity	NPC251579
0.7087	Intermediate Similarity	NPC469891
0.7087	Intermediate Similarity	NPC133135
0.7087	Intermediate Similarity	NPC469892
0.7087	Intermediate Similarity	NPC202986
0.7087	Intermediate Similarity	NPC469890
0.7083	Intermediate Similarity	NPC95429
0.708	Intermediate Similarity	NPC147179
0.708	Intermediate Similarity	NPC9274
0.7071	Intermediate Similarity	NPC25493
0.7071	Intermediate Similarity	NPC113460
0.7069	Intermediate Similarity	NPC183339
0.7069	Intermediate Similarity	NPC234337
0.7069	Intermediate Similarity	NPC133389
0.7069	Intermediate Similarity	NPC68339
0.7064	Intermediate Similarity	NPC11554
0.7059	Intermediate Similarity	NPC152415
0.7059	Intermediate Similarity	NPC245187
0.7059	Intermediate Similarity	NPC316301
0.7059	Intermediate Similarity	NPC27323
0.7054	Intermediate Similarity	NPC196673
0.7054	Intermediate Similarity	NPC715
0.7053	Intermediate Similarity	NPC103387
0.7048	Intermediate Similarity	NPC128248
0.7048	Intermediate Similarity	NPC133809
0.7048	Intermediate Similarity	NPC136810
0.7048	Intermediate Similarity	NPC225079
0.7048	Intermediate Similarity	NPC225506
0.7043	Intermediate Similarity	NPC154030
0.7043	Intermediate Similarity	NPC471671
0.7041	Intermediate Similarity	NPC322387
0.7037	Intermediate Similarity	NPC310456
0.703	Intermediate Similarity	NPC204210
0.703	Intermediate Similarity	NPC306074

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 NPC314690 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	996
0.2-0.3	1399
0.3-0.4	3104
0.4-0.5	2122
0.5-0.6	1058
0.6-0.7	248
0.7-0.8	31
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8283	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD9294	Approved
0.7653	Intermediate Similarity	NPD845	Approved
0.75	Intermediate Similarity	NPD1101	Approved
0.7347	Intermediate Similarity	NPD1090	Approved
0.7347	Intermediate Similarity	NPD1086	Approved
0.7347	Intermediate Similarity	NPD1089	Approved
0.7255	Intermediate Similarity	NPD288	Approved
0.7245	Intermediate Similarity	NPD800	Approved
0.7228	Intermediate Similarity	NPD1693	Approved
0.7228	Intermediate Similarity	NPD4814	Discontinued
0.7207	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1088	Approved
0.7193	Intermediate Similarity	NPD7741	Discontinued
0.7193	Intermediate Similarity	NPD3091	Approved
0.7157	Intermediate Similarity	NPD844	Approved
0.7157	Intermediate Similarity	NPD1809	Phase 2
0.7129	Intermediate Similarity	NPD1409	Phase 3
0.7117	Intermediate Similarity	NPD7635	Approved
0.7075	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6647	Phase 2
0.7059	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6049	Phase 2
0.7043	Intermediate Similarity	NPD2227	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD1087	Approved
0.7009	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD1710	Approved
0.6972	Remote Similarity	NPD6406	Approved
0.6972	Remote Similarity	NPD2342	Discontinued
0.697	Remote Similarity	NPD531	Approved
0.6961	Remote Similarity	NPD3718	Approved
0.6961	Remote Similarity	NPD3719	Approved
0.6952	Remote Similarity	NPD3020	Approved
0.6949	Remote Similarity	NPD3092	Approved
0.6937	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3095	Discontinued
0.6923	Remote Similarity	NPD5125	Phase 3
0.6923	Remote Similarity	NPD5126	Approved
0.6909	Remote Similarity	NPD4718	Approved
0.6909	Remote Similarity	NPD4720	Approved
0.6909	Remote Similarity	NPD4717	Approved
0.6893	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1616	Discontinued
0.6863	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD9612	Approved
0.6857	Remote Similarity	NPD9611	Approved
0.6857	Remote Similarity	NPD9609	Approved
0.6842	Remote Similarity	NPD5951	Approved
0.6837	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD2860	Approved
0.6827	Remote Similarity	NPD2859	Approved
0.6822	Remote Similarity	NPD855	Approved
0.6822	Remote Similarity	NPD854	Approved
0.6822	Remote Similarity	NPD4818	Approved
0.6822	Remote Similarity	NPD4817	Approved
0.6807	Remote Similarity	NPD5618	Discontinued
0.6804	Remote Similarity	NPD3971	Phase 1
0.6792	Remote Similarity	NPD2066	Phase 3
0.678	Remote Similarity	NPD4059	Approved
0.6771	Remote Similarity	NPD9250	Approved
0.6765	Remote Similarity	NPD1239	Approved
0.6765	Remote Similarity	NPD530	Approved
0.6762	Remote Similarity	NPD1566	Phase 3
0.6762	Remote Similarity	NPD1564	Approved
0.6762	Remote Similarity	NPD1565	Approved
0.6759	Remote Similarity	NPD3683	Approved
0.6759	Remote Similarity	NPD3680	Approved
0.6759	Remote Similarity	NPD3682	Approved
0.6759	Remote Similarity	NPD3681	Approved
0.6731	Remote Similarity	NPD2933	Approved
0.6731	Remote Similarity	NPD2934	Approved
0.6724	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD3094	Phase 2
0.6698	Remote Similarity	NPD9495	Approved
0.6667	Remote Similarity	NPD111	Approved
0.6667	Remote Similarity	NPD1989	Approved
0.6667	Remote Similarity	NPD4719	Phase 2
0.6667	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD2932	Approved
0.6639	Remote Similarity	NPD3019	Approved
0.6633	Remote Similarity	NPD9491	Approved
0.6607	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4231	Approved
0.6606	Remote Similarity	NPD5765	Approved
0.6606	Remote Similarity	NPD4229	Approved
0.6581	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD1445	Approved
0.6577	Remote Similarity	NPD1444	Approved
0.6577	Remote Similarity	NPD6685	Approved
0.6574	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5347	Phase 2
0.6569	Remote Similarity	NPD5346	Phase 2
0.6552	Remote Similarity	NPD2629	Approved
0.6549	Remote Similarity	NPD4750	Phase 3
0.6549	Remote Similarity	NPD1792	Phase 2
0.6545	Remote Similarity	NPD311	Approved
0.6545	Remote Similarity	NPD315	Approved
0.6545	Remote Similarity	NPD1237	Approved
0.6545	Remote Similarity	NPD3048	Approved
0.6545	Remote Similarity	NPD3046	Approved
0.6545	Remote Similarity	NPD3047	Approved
0.6545	Remote Similarity	NPD10	Approved
0.6545	Remote Similarity	NPD310	Approved
0.6545	Remote Similarity	NPD314	Approved
0.6545	Remote Similarity	NPD309	Approved
0.6538	Remote Similarity	NPD752	Approved
0.6538	Remote Similarity	NPD9251	Approved
0.6514	Remote Similarity	NPD940	Approved
0.6514	Remote Similarity	NPD846	Approved
0.6505	Remote Similarity	NPD3672	Approved
0.6505	Remote Similarity	NPD3673	Approved
0.65	Remote Similarity	NPD4626	Approved
0.65	Remote Similarity	NPD7725	Approved
0.65	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD1673	Approved
0.648	Remote Similarity	NPD5736	Approved
0.6476	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD1563	Approved
0.6476	Remote Similarity	NPD719	Approved
0.6476	Remote Similarity	NPD720	Approved
0.6471	Remote Similarity	NPD4479	Discontinued
0.6466	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4658	Approved
0.6455	Remote Similarity	NPD1929	Approved
0.6455	Remote Similarity	NPD4656	Approved
0.6455	Remote Similarity	NPD1930	Approved
0.6449	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD226	Approved
0.6408	Remote Similarity	NPD689	Discontinued
0.6404	Remote Similarity	NPD3022	Approved
0.6404	Remote Similarity	NPD3021	Approved
0.64	Remote Similarity	NPD4624	Approved
0.64	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6085	Phase 2
0.6393	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4793	Discontinued
0.6373	Remote Similarity	NPD9538	Approved
0.6364	Remote Similarity	NPD1751	Approved
0.6364	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD3317	Approved
0.6356	Remote Similarity	NPD4198	Discontinued
0.6348	Remote Similarity	NPD4253	Approved
0.6348	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD4254	Approved
0.6339	Remote Similarity	NPD5048	Discontinued
0.6325	Remote Similarity	NPD6010	Discontinued
0.6321	Remote Similarity	NPD1066	Discontinued
0.6316	Remote Similarity	NPD9716	Approved
0.6316	Remote Similarity	NPD2684	Approved
0.6311	Remote Similarity	NPD3895	Approved
0.6311	Remote Similarity	NPD3897	Approved
0.6311	Remote Similarity	NPD3898	Approved
0.6311	Remote Similarity	NPD3896	Approved
0.6308	Remote Similarity	NPD7431	Approved
0.6308	Remote Similarity	NPD7430	Approved
0.6306	Remote Similarity	NPD1415	Approved
0.6304	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD3123	Discovery
0.629	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD4093	Discontinued
0.6281	Remote Similarity	NPD5691	Approved
0.6279	Remote Similarity	NPD6663	Approved
0.6273	Remote Similarity	NPD2553	Approved
0.6273	Remote Similarity	NPD2558	Approved
0.6273	Remote Similarity	NPD2550	Approved
0.6273	Remote Similarity	NPD2552	Approved
0.6273	Remote Similarity	NPD2555	Approved
0.6273	Remote Similarity	NPD2549	Approved
0.6271	Remote Similarity	NPD4766	Approved
0.6271	Remote Similarity	NPD497	Approved
0.627	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.627	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD3772	Phase 3
0.626	Remote Similarity	NPD4097	Suspended
0.625	Remote Similarity	NPD5909	Discontinued
0.625	Remote Similarity	NPD9249	Phase 1
0.625	Remote Similarity	NPD7008	Discontinued
0.625	Remote Similarity	NPD7610	Discontinued
0.624	Remote Similarity	NPD1283	Approved
0.6239	Remote Similarity	NPD1138	Approved
0.6231	Remote Similarity	NPD3620	Phase 2
0.6231	Remote Similarity	NPD4140	Approved
0.6231	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.623	Remote Similarity	NPD2286	Discontinued
0.6228	Remote Similarity	NPD9532	Phase 3
0.6224	Remote Similarity	NPD9490	Approved
0.6218	Remote Similarity	NPD4032	Approved
0.6218	Remote Similarity	NPD4031	Approved
0.6216	Remote Similarity	NPD4189	Approved
0.6216	Remote Similarity	NPD4188	Approved
0.6216	Remote Similarity	NPD4119	Approved
0.6198	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7009	Phase 2
0.6198	Remote Similarity	NPD5304	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