NPASS Compound

Natural Product: NPC9713

Natural Product ID	NPC9713
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IYLRRIUNGGQRTN-NWRWZVFGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	7069830
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003755] Aspidofractine alkaloids

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 51 56 0 0 0 0 0 0 0 0999 V2000 4.1799 -1.2440 2.4494 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0492 -0.7052 1.7961 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0520 -0.4484 0.4484 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1451 -0.7338 -0.1516 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9552 0.0981 -0.3020 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4261 1.4556 0.2114 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1941 1.7664 -0.6576 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2004 3.1900 -0.6160 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0306 3.6521 0.4975 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7730 2.5920 1.2679 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9758 1.4278 1.3165 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4543 0.3362 2.1123 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4786 -0.7583 1.6106 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4746 -0.4901 0.1617 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3598 -1.5084 -0.4777 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7164 -1.6402 -0.6697 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2159 -2.7504 -1.2968 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3800 -3.7653 -1.7530 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0204 -3.6349 -1.5620 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5078 -2.5016 -0.9221 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8519 -2.1195 -0.6200 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7801 -0.6963 -0.6146 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3708 -0.2887 -2.0694 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3887 1.2417 -2.0575 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9318 0.9148 -0.0524 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8735 -2.1085 3.0872 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7017 -0.4706 3.0477 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9015 -1.5818 1.6755 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4163 0.4261 -1.3097 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1440 1.4056 1.2766 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1812 2.2299 0.0649 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7495 3.8042 -0.6292 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6760 3.4382 -1.6112 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4236 4.2208 1.2616 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7867 4.3830 0.1322 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0654 3.0082 2.2465 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7021 2.3698 0.6891 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4912 0.0464 1.9104 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2738 0.5308 3.1713 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4479 -0.7069 2.1610 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9972 -1.7206 1.8720 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3463 -0.8291 -0.3017 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3010 -2.8432 -1.4438 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8477 -4.6007 -2.2328 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3792 -4.4394 -1.9251 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6120 -2.7877 -0.4641 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1192 -0.6814 -2.7614 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6568 -0.6689 -2.2365 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3121 1.6079 -2.5031 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5142 1.5500 -2.6420 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8715 1.0282 -0.5849 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 6 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 14 13 1 1 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 22 21 1 6 22 23 1 0 23 24 1 0 14 25 1 0 22 5 1 0 24 7 1 0 25 7 1 0 25 11 1 0 22 14 1 0 20 15 1 0 1 26 1 0 1 27 1 0 1 28 1 0 5 29 1 6 6 30 1 0 6 31 1 0 8 32 1 0 8 33 1 0 9 34 1 0 9 35 1 0 10 36 1 0 10 37 1 0 12 38 1 0 12 39 1 0 13 40 1 0 13 41 1 0 16 42 1 0 17 43 1 0 18 44 1 0 19 45 1 0 21 46 1 0 23 47 1 0 23 48 1 0 24 49 1 0 24 50 1 0 25 51 1 6 M END

Standard InCHIKey	IYLRRIUNGGQRTN-NWRWZVFGSA-N
Standard InCHI	InChI=1S/C21H26N2O2/c1-25-17(24)15-13-19-7-4-11-23-12-10-20(18(19)23)14-5-2-3-6-16(14)22-21(15,20)9-8-19/h2-3,5-6,15,18,22H,4,7-13H2,1H3/t15-,18-,19+,20+,21+/m0/s1
SMILES	COC(=O)[C@@H]1C[C@@]23CCCN4CC[C@@]5(c6ccccc6N[C@]15CC2)[C@H]34

Calculated Properties

Physi-Chem Properties

Molecular Weight:	338.2	Volume:	349.462 ? Van der Waals volume.
Dense:	0.968	LogP:	2.849 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.83 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.768 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	41.57 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	7.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.8	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.897	Fsp³:	0.667
MCE-18:	156.514 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.281	Fluc inhibitor:	0.006 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.401 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.071 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.026

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.288	MDCK Permeability:	-4.917
Pgp-inhibitor:	0.005	Pgp-substrate:	0.966
PAMPA:	0.016 ? 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):	0.0
20% Bioavailability (F20%):	0.021	30% Bioavailability (F30%):	0.503
50% Bioavailability (F50%):	0.379

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.994	MRP1:	0.96
Plasma Protein Binding (PPB):	69.022%	Volume Distribution (VD):	0.408
Fu:	30.69% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.792
OATP1B3 inhibitor:	0.339	BCRP inhibitor:	0.061
BSEP inhibitor:	0.222

ADMET: Metabolism

CYP1A2-inhibitor:	0.196	CYP1A2-substrate:	0.03
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.943
CYP2D6-inhibitor:	0.619	CYP2D6-substrate:	0.756
CYP3A4-inhibitor:	0.985	CYP3A4-substrate:	0.931
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.002
HLM stability:	0.365 ? 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):

7.264

Half-life (T1/2):

1.54

ADMET: Toxicity

hERG Blockers:	0.337	hERG Blockers (10um):	0.542
Human Hepatotoxicity (H-HT):	0.769	Drug-induced Liver Injury (DILI):	0.043
AMES Toxicity:	0.342	Rat Oral Acute Toxicity:	0.91
Maximum Recommended Daily Dose:	0.901	Skin Sensitization:	0.959
Carcinogencity:	0.796	Eye Corrosion:	0.001
Eye Irritation:	0.129	Respiratory Toxicity:	0.98
Drug-induced Neurotoxicity:	0.46	Ototoxicity:	0.288
Hematotoxicity:	0.229	Drug-induced Nephrotoxicity:	0.776
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.015
A549 Cytotoxicity:	0.207	Hek293 Cytotoxicity:	0.547
BCF:	1.504 ? 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:	4.003 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.318 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.867 ? 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
NPO3634	Robinia pseudoacacia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11551759]
NPO18923	Coleus xanthanthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027731]
NPO10	Alexandrium ostenfeldii	Species	Pyrocystaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872129]
NPO10	Alexandrium ostenfeldii	Species	Pyrocystaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19572609]
NPO3634	Robinia pseudoacacia	Species	Fabaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21214467]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21428274]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[21428274]
NPO17129	Melodinus hemsleyanus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32683864]
NPO10	Alexandrium ostenfeldii	Species	Pyrocystaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3634	Robinia pseudoacacia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3460	Vepris uguenensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28069.1	Artemisia cana subsp. viscidula	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3679	Psilocybe baeocystis	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17129	Melodinus hemsleyanus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18923	Coleus xanthanthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20028	Lethariella sernanderi	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13485	Prismatomeris sessiliflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21640	Pygmaeopremna herbacea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21313	Rabdosia lasiocarpa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17662	Scutellaria glabrata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8358	Senecio halimifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7972	Solaster endeca	Species	Solasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17897	Streptomyces albospinus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19196	Lecocarpus pinnatifidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1824	Callitris rhomboidea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3634	Robinia pseudoacacia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18923	Coleus xanthanthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3634	Robinia pseudoacacia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17129	Melodinus hemsleyanus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18923	Coleus xanthanthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21640	Pygmaeopremna herbacea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO28069.1	Artemisia cana subsp. viscidula	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3634	Robinia pseudoacacia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3634	Robinia pseudoacacia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28069.1	Artemisia cana subsp. viscidula	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2744	Aphloia madagascariensis	Species	Aphloiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21640	Pygmaeopremna herbacea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7972	Solaster endeca	Species	Solasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13485	Prismatomeris sessiliflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8358	Senecio halimifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20028	Lethariella sernanderi	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18923	Coleus xanthanthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17662	Scutellaria glabrata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3679	Psilocybe baeocystis	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17897	Streptomyces albospinus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21313	Rabdosia lasiocarpa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3460	Vepris uguenensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1824	Callitris rhomboidea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO671	Kopsia larutensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19196	Lecocarpus pinnatifidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17129	Melodinus hemsleyanus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10	Alexandrium ostenfeldii	Species	Pyrocystaceae	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
EC50	1

Activity Type	# Activity
Tissue	1

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
NPT26252	Tissue	Aortic artery	Rattus norvegicus	EC50	>	10000.0	nM	PMID[32683864]

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 NPC9713 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	27059
0.1-0.2	22394
0.2-0.3	345
0.3-0.4	42
0.4-0.5	9
0.5-0.6	4
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC99632
1.0	High Similarity	NPC282339
0.6883	Remote Similarity	NPC483474
0.68	Remote Similarity	NPC483476
0.6625	Remote Similarity	NPC483472
0.5432	Remote Similarity	NPC137589
0.5412	Remote Similarity	NPC52262
0.5229	Remote Similarity	NPC483481
0.5135	Remote Similarity	NPC483482

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC9713 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3450
0.1-0.2	5555
0.2-0.3	145
0.3-0.4	0
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