NPASS Compound

Natural Product: NPC222522

Natural Product ID	NPC222522
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-(8Z-Heptadecenyl)-1,3-Benzenediol
IUPAC Name	5-[(Z)-heptadec-8-enyl]benzene-1,3-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL462807
PubChem CID	14235910
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 63 63 0 0 0 0 0 0 0 0999 V2000 -9.6176 -0.3833 0.3608 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1178 -0.8323 0.4910 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7283 -1.1961 -0.8902 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4260 -1.7507 -1.2144 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1451 -1.0583 -0.9639 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7219 -0.7830 0.4140 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4980 0.0081 0.6817 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1989 -0.4362 0.1437 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0575 -0.3553 -1.2946 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1342 0.4207 -1.8609 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1961 1.2487 -1.1157 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2102 0.7546 -1.4898 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2977 1.5143 -0.8051 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2441 1.4386 0.6889 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3670 2.2154 1.3432 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7184 1.7195 0.9464 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9359 0.2696 1.3200 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2842 -0.2042 0.9174 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3682 -0.0917 1.7887 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6228 -0.5245 1.4332 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8687 -1.0878 0.2049 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8052 -1.2075 -0.6724 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5468 -0.7717 -0.3122 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0691 -1.7837 -1.9224 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6725 -0.3965 2.3233 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6815 0.3911 -0.4197 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2006 -1.2652 0.0615 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9805 -0.0547 1.3516 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6147 0.0833 0.8938 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1361 -1.6887 1.1546 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0281 -0.3579 -1.6151 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4988 -1.9956 -1.2068 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3630 -2.7902 -0.7513 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4515 -1.9871 -2.3429 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3768 -1.8750 -1.3226 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9484 -0.2348 -1.6575 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5294 -0.2696 1.0323 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5591 -1.7629 0.9966 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6824 1.1119 0.4185 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3774 0.0204 1.8295 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0879 -1.5741 0.4098 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3351 -0.0323 0.7350 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6768 -0.9249 -2.0087 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0587 0.4528 -2.9532 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2619 1.2724 -0.0445 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2717 2.3405 -1.4395 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2476 -0.2962 -1.1049 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3315 0.6924 -2.5765 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3164 2.5630 -1.1673 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2616 1.0688 -1.1385 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3044 1.9746 1.0136 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1532 0.4081 1.0317 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2747 3.2629 0.9755 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2050 2.1900 2.4204 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4705 2.3060 1.5162 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9251 1.8791 -0.1143 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8228 0.1000 2.3946 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1390 -0.3197 0.8029 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1682 0.3560 2.7624 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8742 -1.4314 -0.0719 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7132 -0.8747 -1.0222 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2469 -1.1313 -2.6950 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4967 -0.3103 3.3364 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 20 25 1 0 23 18 1 0 1 26 1 0 1 27 1 0 1 28 1 0 2 29 1 0 2 30 1 0 3 31 1 0 3 32 1 0 4 33 1 0 4 34 1 0 5 35 1 0 5 36 1 0 6 37 1 0 6 38 1 0 7 39 1 0 7 40 1 0 8 41 1 0 8 42 1 0 9 43 1 0 10 44 1 0 11 45 1 0 11 46 1 0 12 47 1 0 12 48 1 0 13 49 1 0 13 50 1 0 14 51 1 0 14 52 1 0 15 53 1 0 15 54 1 0 16 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 19 59 1 0 21 60 1 0 23 61 1 0 24 62 1 0 25 63 1 0 M END

Standard InCHIKey	DQSWQRFGZIJUCI-KTKRTIGZSA-N
Standard InCHI	InChI=1S/C23H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21-18-22(24)20-23(25)19-21/h9-10,18-20,24-25H,2-8,11-17H2,1H3/b10-9-
SMILES	CCCCCCCC/C=CCCCCCCCc1cc(cc(c1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	346.29	Volume:	404.842 ? Van der Waals volume.
Dense:	0.855	LogP:	9.134 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.148 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.119 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	7.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	1.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.258	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.316	Fsp³:	0.652
MCE-18:	6.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.732	Fluc inhibitor:	0.352 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.053 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.947	Promiscuous compounds:	0.084

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.243	MDCK Permeability:	-4.708
Pgp-inhibitor:	0.391	Pgp-substrate:	0.0
PAMPA:	0.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.859	30% Bioavailability (F30%):	0.946
50% Bioavailability (F50%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04	MRP1:	0.949
Plasma Protein Binding (PPB):	99.118%	Volume Distribution (VD):	0.526
Fu:	0.249% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.15
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.869
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.551
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.996
CYP2D6-inhibitor:	0.989	CYP2D6-substrate:	0.998
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.142 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

4.103

Half-life (T1/2):

1.03

ADMET: Toxicity

hERG Blockers:	0.708	hERG Blockers (10um):	0.905
Human Hepatotoxicity (H-HT):	0.315	Drug-induced Liver Injury (DILI):	0.003
AMES Toxicity:	0.152	Rat Oral Acute Toxicity:	0.138
Maximum Recommended Daily Dose:	0.599	Skin Sensitization:	1.0
Carcinogencity:	0.099	Eye Corrosion:	0.989
Eye Irritation:	0.997	Respiratory Toxicity:	0.807
Drug-induced Neurotoxicity:	0.016	Ototoxicity:	0.125
Hematotoxicity:	0.011	Drug-induced Nephrotoxicity:	0.16
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.064
A549 Cytotoxicity:	0.95	Hek293 Cytotoxicity:	0.889
BCF:	1.205 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	5.142 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.107 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.793 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO25294	Merulius incarnatus	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643059]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17124632]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17124632]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	roots	n.a.	n.a.	PMID[17125236]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125236]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25294	Merulius incarnatus	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25294	Merulius incarnatus	Species	Meruliaceae	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	Organism Name	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	7

Activity Type	# Activity
Cell line	5
Organism	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell line	A549	Homo sapiens	IC50	=	460.0	nM	PMID[18926710]
NPT179	Cell line	A2780	Homo sapiens	IC50	=	1060.0	nM	PMID[20363140]
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	=	1070.0	nM	PMID[21910504]
NPT547	Cell line	BGC-823	Homo sapiens	IC50	=	1430.0	nM	PMID[16180824]
NPT180	Cell line	HCT-8	Homo sapiens	IC50	=	780.0	nM	PMID[19691293]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IC50	=	10.0	ug.mL-1	PMID[26890118]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	8.0	ug.mL-1	DrugMatrix in vivo data: Pathology

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC222522 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	26982
0.1-0.2	20632
0.2-0.3	1936
0.3-0.4	177
0.4-0.5	47
0.5-0.6	30
0.6-0.7	14
0.7-0.8	0
0.8-0.85	9
0.85-0.9	2
0.9-0.95	8
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC146798
1.0	High Similarity	NPC106396
1.0	High Similarity	NPC94351
1.0	High Similarity	NPC168303
0.9697	High Similarity	NPC53051
0.9697	High Similarity	NPC24404
0.9697	High Similarity	NPC313030
0.9167	High Similarity	NPC71002
0.9167	High Similarity	NPC249828
0.9091	High Similarity	NPC470700
0.9091	High Similarity	NPC54844
0.9091	High Similarity	NPC39097
0.9091	High Similarity	NPC302681
0.9091	High Similarity	NPC118286
0.9091	High Similarity	NPC109691
0.8649	High Similarity	NPC302219
0.8571	High Similarity	NPC39664
0.8182	Intermediate Similarity	NPC294186
0.8182	Intermediate Similarity	NPC147310
0.8182	Intermediate Similarity	NPC137415
0.8182	Intermediate Similarity	NPC166313
0.8182	Intermediate Similarity	NPC192032
0.8182	Intermediate Similarity	NPC24407
0.8182	Intermediate Similarity	NPC11280
0.8158	Intermediate Similarity	NPC242342
0.8158	Intermediate Similarity	NPC85479
0.7895	Intermediate Similarity	NPC166761
0.7692	Intermediate Similarity	NPC10588
0.7674	Intermediate Similarity	NPC305603
0.75	Intermediate Similarity	NPC72947
0.7273	Intermediate Similarity	NPC246056
0.725	Intermediate Similarity	NPC94139
0.725	Intermediate Similarity	NPC284011
0.725	Intermediate Similarity	NPC147284
0.7179	Intermediate Similarity	NPC232523
0.7	Intermediate Similarity	NPC488413
0.7	Intermediate Similarity	NPC483454
0.7	Intermediate Similarity	NPC162314
0.7	Intermediate Similarity	NPC488412
0.6889	Remote Similarity	NPC61033
0.675	Remote Similarity	NPC486908
0.6667	Remote Similarity	NPC123559
0.6522	Remote Similarity	NPC127894
0.6522	Remote Similarity	NPC470759
0.6364	Remote Similarity	NPC210497
0.6327	Remote Similarity	NPC140521
0.6279	Remote Similarity	NPC158253
0.6154	Remote Similarity	NPC241891
0.6154	Remote Similarity	NPC134829
0.6098	Remote Similarity	NPC55561
0.6087	Remote Similarity	NPC470760
0.6047	Remote Similarity	NPC129373
0.6047	Remote Similarity	NPC488416
0.5952	Remote Similarity	NPC196479
0.5952	Remote Similarity	NPC487734
0.587	Remote Similarity	NPC483450
0.5854	Remote Similarity	NPC177420
0.575	Remote Similarity	NPC3358
0.575	Remote Similarity	NPC306884
0.575	Remote Similarity	NPC603092
0.5652	Remote Similarity	NPC192
0.5652	Remote Similarity	NPC219070
0.5652	Remote Similarity	NPC483449
0.5641	Remote Similarity	NPC59506
0.5625	Remote Similarity	NPC486909
0.561	Remote Similarity	NPC487946
0.561	Remote Similarity	NPC487945
0.56	Remote Similarity	NPC17840
0.56	Remote Similarity	NPC247477
0.5556	Remote Similarity	NPC204901
0.551	Remote Similarity	NPC249836
0.55	Remote Similarity	NPC488411
0.55	Remote Similarity	NPC488410
0.55	Remote Similarity	NPC488409
0.5385	Remote Similarity	NPC123273
0.5385	Remote Similarity	NPC318325
0.5349	Remote Similarity	NPC280347
0.5319	Remote Similarity	NPC48730
0.5294	Remote Similarity	NPC470699
0.525	Remote Similarity	NPC37802
0.5217	Remote Similarity	NPC114064
0.52	Remote Similarity	NPC15860
0.5111	Remote Similarity	NPC487735

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC222522 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6245
0.1-0.2	2770
0.2-0.3	126
0.3-0.4	6
0.4-0.5	3
0.5-0.6	0
0.6-0.7	0
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
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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