NPASS Compound

Natural Product: NPC90489

Natural Product ID	NPC90489
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KYQZWONCHDNPDP-NFRVFMFJSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44257214
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0000507] Isoflavonoid O-glycosides

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 50 53 0 0 0 0 0 0 0 0999 V2000 6.1848 -0.8312 1.4032 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5581 -0.9826 1.3645 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2248 -0.6267 0.2175 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5363 -0.1322 -0.8630 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1454 0.0092 -0.7927 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4584 -0.3406 0.3448 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0149 -0.1742 0.3663 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3362 0.3837 1.4323 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0246 0.5321 1.4456 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2523 0.1644 0.4516 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1389 0.3461 0.5191 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9633 -0.0348 -0.5163 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3657 -0.6158 -1.6527 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9978 -0.7767 -1.6810 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8399 -0.4030 -0.6572 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2095 -0.5711 -0.6999 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7440 -1.0834 -1.6999 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3261 0.0948 -0.5568 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0902 0.6344 0.4483 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7413 1.8958 -0.0914 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8221 1.5550 -1.1050 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7891 0.6318 -0.4215 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0375 -0.5625 0.0928 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0366 -1.4401 0.8278 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4559 -2.5991 1.2999 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0319 -0.2374 0.9855 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4046 1.3303 0.6229 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3228 1.0343 -2.2722 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3498 2.5765 0.9478 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6184 -0.7825 0.1842 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6837 -1.1174 2.3145 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1340 -1.3688 2.1964 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0393 0.1527 -1.7716 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6113 0.4003 -1.6504 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9519 0.6995 2.2747 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5550 0.7996 1.4180 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0142 -0.9164 -2.4694 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4498 -1.2221 -2.5535 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4666 0.9525 1.2972 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9847 2.4890 -0.6070 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3274 2.5191 -1.3438 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5363 0.2579 -1.1531 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6549 -1.1474 -0.7462 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5287 -0.8552 1.6428 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8735 -1.7368 0.1450 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5623 -3.3044 0.6181 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6269 2.2253 0.2671 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0616 0.0990 -2.2479 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9626 3.4731 1.0638 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0151 -1.3943 -0.5277 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 12 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 23 26 1 0 22 27 1 0 21 28 1 0 20 29 1 0 3 30 1 0 6 1 1 0 16 7 1 0 26 19 1 0 15 10 1 0 1 31 1 0 2 32 1 0 4 33 1 0 5 34 1 0 8 35 1 0 11 36 1 0 13 37 1 0 14 38 1 0 19 39 1 1 20 40 1 0 21 41 1 6 22 42 1 6 23 43 1 0 24 44 1 0 24 45 1 0 25 46 1 0 27 47 1 0 28 48 1 0 29 49 1 0 30 50 1 0 M END

Standard InCHIKey	KYQZWONCHDNPDP-NFRVFMFJSA-N
Standard InCHI	InChI=1S/C21H20O9/c22-8-16-18(25)19(26)20(27)21(30-16)29-12-5-6-13-15(7-12)28-9-14(17(13)24)10-1-3-11(23)4-2-10/h1-7,9,16,18-23,25-27H,8H2/t16?,18-,19+,20?,21-/m1/s1
SMILES	c1cc(ccc1c1coc2cc(ccc2c1=O)O[C@H]1C([C@H]([C@@H](C(CO)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	416.11	Volume:	395.567 ? Van der Waals volume.
Dense:	1.052	LogP:	0.109 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.074 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.456 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	24.0
TPSA:	149.82 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.406	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.66	Fsp³:	0.286
MCE-18:	80.889 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.535	Fluc inhibitor:	0.378 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.945 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.764 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.318	Promiscuous compounds:	0.229

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.332	MDCK Permeability:	-5.104
Pgp-inhibitor:	0.0	Pgp-substrate:	0.438
PAMPA:	1.0 ? 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):	0.838
20% Bioavailability (F20%):	0.783	30% Bioavailability (F30%):	0.98
50% Bioavailability (F50%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.418
Plasma Protein Binding (PPB):	76.33%	Volume Distribution (VD):	0.113
Fu:	28.017% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.885
OATP1B3 inhibitor:	0.992	BCRP inhibitor:	0.043
BSEP inhibitor:	0.018

ADMET: Metabolism

CYP1A2-inhibitor:	0.11	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.007
CYP2C9-inhibitor:	0.576	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.003	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.997
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.0 ? 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):

3.18

Half-life (T1/2):

2.853

ADMET: Toxicity

hERG Blockers:	0.131	hERG Blockers (10um):	0.344
Human Hepatotoxicity (H-HT):	0.628	Drug-induced Liver Injury (DILI):	0.759
AMES Toxicity:	0.678	Rat Oral Acute Toxicity:	0.169
Maximum Recommended Daily Dose:	0.187	Skin Sensitization:	0.655
Carcinogencity:	0.391	Eye Corrosion:	0.0
Eye Irritation:	0.23	Respiratory Toxicity:	0.051
Drug-induced Neurotoxicity:	0.086	Ototoxicity:	0.897
Hematotoxicity:	0.133	Drug-induced Nephrotoxicity:	0.453
Genotoxicity:	0.619	RPMI-8226 Immunitoxicity:	0.079
A549 Cytotoxicity:	0.148	Hek293 Cytotoxicity:	0.454
BCF:	0.497 ? 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:	3.187 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.765 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.872 ? 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
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	WrocÃ…â€šaw, Poland	2004Ã¢â‚¬â€œ2005	DOI[10.1016/J.FOODCHEM.2006.08.014]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003Ã¢â‚¬â€œ2005	DOI[10.1016/j.jfca.2006.05.007]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0021-9258(18)90865-3]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0168-9452(02)00136-X]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0168-9452(02)00136-X]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jf950732o]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1023/A:1024390522259]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10775096]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[1622242]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16659156]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16668466]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20963508]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seeds	Tekirdag, Turkey		PMID[24499198]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25053043]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25070365]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[25369450]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25369450]
NPO30303	Pueraria lobata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25679337]
NPO30303	Pueraria lobata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5939	Semen sojae praeparata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8707.1	Pueraria montana var. lobata	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Hypocotyl	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO30892	Pueraria thomsonii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9177	Semen sojae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30303	Pueraria lobata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8707.1	Pueraria montana var. lobata	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5939	Semen sojae praeparata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO8707.2	Pueraria montana var. thomsonii	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9177	Semen sojae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO30892	Pueraria thomsonii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30303	Pueraria lobata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9177	Semen sojae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8707.1	Pueraria montana var. lobata	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8707.2	Pueraria montana var. thomsonii	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8707.2	Pueraria montana var. thomsonii	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8707.1	Pueraria montana var. lobata	Varieties	Fabaceae	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 NPC90489 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	18750
0.1-0.2	26631
0.2-0.3	3211
0.3-0.4	935
0.4-0.5	259
0.5-0.6	38
0.6-0.7	16
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC161749
0.8429	Intermediate Similarity	NPC211014
0.8286	Intermediate Similarity	NPC45165
0.7867	Intermediate Similarity	NPC229729
0.7808	Intermediate Similarity	NPC105511
0.7568	Intermediate Similarity	NPC197896
0.7568	Intermediate Similarity	NPC258035
0.7568	Intermediate Similarity	NPC313163
0.7403	Intermediate Similarity	NPC601607
0.7368	Intermediate Similarity	NPC100720
0.7143	Intermediate Similarity	NPC205076
0.7123	Intermediate Similarity	NPC25547
0.6842	Remote Similarity	NPC135345
0.6582	Remote Similarity	NPC73511
0.6538	Remote Similarity	NPC259070
0.6471	Remote Similarity	NPC181124
0.6456	Remote Similarity	NPC156457
0.6395	Remote Similarity	NPC479405
0.6329	Remote Similarity	NPC348541
0.6322	Remote Similarity	NPC479404
0.625	Remote Similarity	NPC603782
0.622	Remote Similarity	NPC80140
0.619	Remote Similarity	NPC479407
0.6154	Remote Similarity	NPC231194
0.6071	Remote Similarity	NPC479406
0.6049	Remote Similarity	NPC168822
0.6049	Remote Similarity	NPC234739
0.6	Remote Similarity	NPC48773
0.5934	Remote Similarity	NPC51326
0.5882	Remote Similarity	NPC307518
0.5833	Remote Similarity	NPC479402
0.5745	Remote Similarity	NPC235575
0.5714	Remote Similarity	NPC138540
0.5679	Remote Similarity	NPC487214
0.5647	Remote Similarity	NPC224462
0.5647	Remote Similarity	NPC479401
0.561	Remote Similarity	NPC160515
0.5542	Remote Similarity	NPC39360
0.5542	Remote Similarity	NPC29763
0.5542	Remote Similarity	NPC210003
0.5495	Remote Similarity	NPC303913
0.5467	Remote Similarity	NPC103409
0.5465	Remote Similarity	NPC481043
0.5412	Remote Similarity	NPC610763
0.5341	Remote Similarity	NPC607201
0.534	Remote Similarity	NPC76047
0.5319	Remote Similarity	NPC479403
0.5294	Remote Similarity	NPC93337
0.5294	Remote Similarity	NPC297987
0.5294	Remote Similarity	NPC323593
0.5294	Remote Similarity	NPC203500
0.5278	Remote Similarity	NPC605229
0.5233	Remote Similarity	NPC105025
0.5227	Remote Similarity	NPC43761
0.5227	Remote Similarity	NPC610187
0.5176	Remote Similarity	NPC58053
0.5176	Remote Similarity	NPC83283
0.5119	Remote Similarity	NPC124478
0.5116	Remote Similarity	NPC95090
0.5116	Remote Similarity	NPC146792
0.5116	Remote Similarity	NPC27408
0.507	Remote Similarity	NPC182428
0.5062	Remote Similarity	NPC191154
0.5057	Remote Similarity	NPC186807
0.5057	Remote Similarity	NPC24043
0.5057	Remote Similarity	NPC100818

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC90489 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4526
0.1-0.2	4477
0.2-0.3	132
0.3-0.4	10
0.4-0.5	1
0.5-0.6	1
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4381	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3818	Discontinued
0.5119	Remote Similarity	NPD4380	Phase 2

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