NPASS Compound

Natural Product: NPC135452

Natural Product ID	NPC135452
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JRFVOMWWESIGRR-OAHLLOKOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	46210886
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

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 52 55 0 0 0 0 0 0 0 0999 V2000 -1.7216 2.1425 0.6729 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5724 1.9349 0.0638 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5649 1.3903 0.7923 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7041 1.2160 -0.1769 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5111 0.4581 -1.3278 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5405 0.2925 -2.2353 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7841 0.8500 -2.0636 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9533 1.6059 -0.9025 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9305 1.7747 0.0059 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2156 2.1882 -0.7010 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4050 2.9603 0.4731 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8124 0.6803 -2.9757 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3578 0.1544 1.5447 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2180 -0.0530 2.6111 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0903 -1.1892 3.3760 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1118 -2.1178 3.0855 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7370 -1.9151 2.0344 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7098 -2.8243 1.7327 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8248 -3.8524 2.4267 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5354 -2.5790 0.6705 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3844 -1.4353 -0.0769 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2155 -1.0994 -1.2231 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8851 -0.0282 -2.0418 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6537 0.3656 -3.1279 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8064 -0.3339 -3.4230 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1674 -1.3968 -2.6413 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3572 -1.7674 -1.5403 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4218 -0.5554 0.2374 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6308 -0.7701 1.2392 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4922 -3.5138 0.4023 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0459 -3.2802 3.8417 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2122 0.8644 2.9294 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5951 2.5512 0.1534 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7890 1.8931 1.7285 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4945 2.1781 -0.9765 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9592 2.1877 1.5360 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5399 -0.0025 -1.5103 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3828 -0.3004 -3.1326 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0970 2.3841 0.9017 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2737 2.3427 1.3809 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7160 3.8515 0.4879 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4320 3.4060 0.4217 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7570 0.9054 -2.7161 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7492 -1.3919 4.2261 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9794 0.5110 -1.8229 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3676 1.2024 -3.7389 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4381 -0.0483 -4.2771 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0669 -1.9552 -2.8569 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7113 -2.6013 -0.9684 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1954 -4.4639 0.2274 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2912 -4.1387 3.4096 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1888 1.3222 3.8442 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 7 12 1 0 3 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 21 28 1 0 28 29 1 0 20 30 1 0 16 31 1 0 14 32 1 0 9 4 1 0 29 13 1 0 29 17 2 0 27 22 1 0 1 33 1 0 1 34 1 0 2 35 1 0 3 36 1 1 5 37 1 0 6 38 1 0 9 39 1 0 11 40 1 0 11 41 1 0 11 42 1 0 12 43 1 0 15 44 1 0 23 45 1 0 24 46 1 0 25 47 1 0 26 48 1 0 27 49 1 0 30 50 1 0 31 51 1 0 32 52 1 0 M END

Standard InCHIKey	JRFVOMWWESIGRR-OAHLLOKOSA-N
Standard InCHI	InChI=1S/C25H20O7/c1-3-15(14-9-10-16(26)19(11-14)31-2)20-17(27)12-18(28)21-22(29)23(30)24(32-25(20)21)13-7-5-4-6-8-13/h3-12,15,26-28,30H,1H2,2H3/t15-/m1/s1
SMILES	C=C[C@H](c1ccc(c(c1)OC)O)c1c(cc(c2c(=O)c(c(c3ccccc3)oc12)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	432.12	Volume:	436.624 ? Van der Waals volume.
Dense:	0.99	LogP:	3.323 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.926 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.426 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	25.0
TPSA:	120.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.34	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.347	Fsp³:	0.08
MCE-18:	50.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.976	Fluc inhibitor:	0.654 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.61 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.651 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.425	Promiscuous compounds:	0.508

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.269	MDCK Permeability:	-4.829
Pgp-inhibitor:	0.895	Pgp-substrate:	0.004
PAMPA:	0.077 ? 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%):	0.08	30% Bioavailability (F30%):	0.928
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.983
Plasma Protein Binding (PPB):	98.323%	Volume Distribution (VD):	-0.559
Fu:	0.931% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.977
BSEP inhibitor:	0.994

ADMET: Metabolism

CYP1A2-inhibitor:	0.053	CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	0.601	CYP2C19-substrate:	0.998
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.643	CYP2D6-substrate:	0.831
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.91
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.447 ? 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):

3.373

Half-life (T1/2):

1.684

ADMET: Toxicity

hERG Blockers:	0.091	hERG Blockers (10um):	0.365
Human Hepatotoxicity (H-HT):	0.797	Drug-induced Liver Injury (DILI):	0.924
AMES Toxicity:	0.251	Rat Oral Acute Toxicity:	0.675
Maximum Recommended Daily Dose:	0.968	Skin Sensitization:	0.671
Carcinogencity:	0.064	Eye Corrosion:	0.001
Eye Irritation:	0.89	Respiratory Toxicity:	0.984
Drug-induced Neurotoxicity:	0.128	Ototoxicity:	0.135
Hematotoxicity:	0.027	Drug-induced Nephrotoxicity:	0.072
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.07
A549 Cytotoxicity:	0.639	Hek293 Cytotoxicity:	0.598
BCF:	1.172 ? 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:	4.274 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.103 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.808 ? 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
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17548953]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[20166702]
NPO40884	Mexican propolis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20307087]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21114277]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21171571]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24675423]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Bako, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Enemore, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Gedo, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Holleta, Ethiopia		PMID[24926420]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29094598]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14169	Acrocarpia paniculata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13876	Cedrela salvadorensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13669	Hertia cheirifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9569	Licaria chrysophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13178	Ornithoglossum viride	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4700	Pertusaria truncata	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14369	Pocillopora eydouxi	Species	Pocilloporidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14470	Polypodium decumanum	Species	Polypodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5280	Rubia tetragona	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12521	Sphaeranthus confertifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO40884	Mexican propolis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5280	Rubia tetragona	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14369	Pocillopora eydouxi	Species	Pocilloporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4700	Pertusaria truncata	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12521	Sphaeranthus confertifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14470	Polypodium decumanum	Species	Polypodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14169	Acrocarpia paniculata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13178	Ornithoglossum viride	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13876	Cedrela salvadorensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9569	Licaria chrysophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13669	Hertia cheirifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11266	Garcinia cambogia	Species	Clusiaceae	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

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

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 NPC135452 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	24335
0.1-0.2	21706
0.2-0.3	3456
0.3-0.4	320
0.4-0.5	39
0.5-0.6	2
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	Natural Product ID
0.5493	Remote Similarity	NPC603348
0.5132	Remote Similarity	NPC607815

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC135452 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3851
0.1-0.2	5214
0.2-0.3	80
0.3-0.4	4
0.4-0.5	0
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