NPASS Compound

Natural Product: NPC141529

Natural Product ID	NPC141529
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YRXTUYZHIHAYPF-LHSJRXKWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	52326161
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

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 56 57 0 0 0 0 0 0 0 0999 V2000 -6.8807 -0.4860 -1.2035 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1237 0.0469 -0.2624 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4035 -0.8148 0.6904 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9420 -0.5775 0.5844 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1154 -1.2687 -0.2638 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7570 -1.0261 -0.3413 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2088 -0.0550 0.4613 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0018 0.6747 1.3387 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3552 0.3911 1.3757 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4730 1.6593 2.1585 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3497 2.3535 3.0210 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1228 0.2021 0.4040 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7340 1.1430 -0.4581 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3101 2.2341 0.4021 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7758 0.4626 -1.3121 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7247 -0.3435 -0.4976 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5627 -1.7026 -0.3056 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4428 -2.4495 0.4501 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5364 -1.8697 1.0555 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7118 -0.5144 0.8734 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8265 0.2211 0.1167 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8272 0.0474 1.4974 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0213 1.4385 1.3198 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4347 -2.6204 1.8244 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4086 1.3206 -2.1755 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1949 1.0456 -3.5133 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9916 -1.7790 -1.2345 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5944 -2.7733 -2.0473 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4266 0.1179 -1.9237 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9820 -1.5520 -1.2879 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0279 1.1219 -0.1854 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6553 -1.8814 0.5443 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7087 -0.5723 1.7374 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5503 -2.0294 -0.8911 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0036 0.9444 2.0517 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8396 3.1324 3.6095 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7927 1.5800 3.6986 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2091 2.7819 2.4452 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0746 1.5953 -1.0645 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0650 2.8375 -0.1637 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7216 1.8511 1.3570 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5103 2.9637 0.6790 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2250 -0.2713 -1.9526 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6917 -2.1606 -0.7890 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3005 -3.5087 0.5890 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9848 1.2803 -0.0116 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0324 1.6424 0.2126 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0954 1.9342 1.7108 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9354 1.8154 1.7799 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3835 -2.2903 1.9635 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6958 1.7249 -4.1975 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4481 -0.0366 -3.6944 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1027 1.1260 -3.6973 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9119 -3.1623 -2.8089 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9790 -3.6041 -1.4089 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4683 -2.3404 -2.5914 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 12 13 1 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 19 24 1 0 15 25 1 0 25 26 1 0 6 27 1 0 27 28 1 0 9 4 1 0 21 16 1 0 1 29 1 0 1 30 1 0 2 31 1 0 3 32 1 0 3 33 1 0 5 34 1 0 9 35 1 0 11 36 1 0 11 37 1 0 11 38 1 0 13 39 1 6 14 40 1 0 14 41 1 0 14 42 1 0 15 43 1 6 17 44 1 0 18 45 1 0 21 46 1 0 23 47 1 0 23 48 1 0 23 49 1 0 24 50 1 0 26 51 1 0 26 52 1 0 26 53 1 0 28 54 1 0 28 55 1 0 28 56 1 0 M END

Standard InCHIKey	YRXTUYZHIHAYPF-LHSJRXKWSA-N
Standard InCHI	InChI=1S/C22H28O6/c1-7-8-15-11-19(25-4)22(20(12-15)26-5)28-14(2)21(27-6)16-9-10-17(23)18(13-16)24-3/h7,9-14,21,23H,1,8H2,2-6H3/t14-,21+/m0/s1
SMILES	C=CCc1cc(c(c(c1)OC)O[C@@H](C)[C@H](c1ccc(c(c1)OC)O)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	388.19	Volume:	406.241 ? Van der Waals volume.
Dense:	0.956	LogP:	3.133 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.122 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.218 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	13.0
TPSA:	66.38 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	1.0	Rings:	2.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.612	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.326	Fsp³:	0.364
MCE-18:	30.0 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.144	Fluc inhibitor:	0.296 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.026 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.323 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.447	Promiscuous compounds:	0.059

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.619	MDCK Permeability:	-4.661
Pgp-inhibitor:	0.602	Pgp-substrate:	0.001
PAMPA:	0.003 ? 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%):	0.235	30% Bioavailability (F30%):	0.428
50% Bioavailability (F50%):	0.911

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.806
Plasma Protein Binding (PPB):	92.793%	Volume Distribution (VD):	0.147
Fu:	8.272% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.123
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.348	CYP1A2-substrate:	0.867
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.5
CYP2C9-inhibitor:	0.901	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.95	CYP2D6-substrate:	0.998
CYP3A4-inhibitor:	0.994	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.016	CYP2C8-inhibitor:	1.0
HLM stability:	0.033 ? 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):

9.27

Half-life (T1/2):

1.517

ADMET: Toxicity

hERG Blockers:	0.245	hERG Blockers (10um):	0.754
Human Hepatotoxicity (H-HT):	0.509	Drug-induced Liver Injury (DILI):	0.398
AMES Toxicity:	0.385	Rat Oral Acute Toxicity:	0.452
Maximum Recommended Daily Dose:	0.564	Skin Sensitization:	0.83
Carcinogencity:	0.416	Eye Corrosion:	0.159
Eye Irritation:	0.907	Respiratory Toxicity:	0.84
Drug-induced Neurotoxicity:	0.764	Ototoxicity:	0.388
Hematotoxicity:	0.187	Drug-induced Nephrotoxicity:	0.311
Genotoxicity:	0.218	RPMI-8226 Immunitoxicity:	0.123
A549 Cytotoxicity:	0.288	Hek293 Cytotoxicity:	0.516
BCF:	1.263 ? 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:	3.698 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.069 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.347 ? 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
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17998162]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955885]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20879744]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27419473]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32515616]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33444950]
NPO7237	Xanthostemon oppositifolius	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2665	Andinobates fulguritus	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17811	Cephalonoplos segetum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5162	Comaster multifida	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8532	Helipterum tenellum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5334	Rhodotypos scandens	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6113	Piper pedicellosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5746	Pancratium trianthum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO490	Lophozonia menziesii	Species	Nothofagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28409	Lens phaseoloides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19928	Lachnoanaerobaculum saburreum	Species	Lachnospiraceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4539	Ipomoea cristulata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7393	Esenbeckia nesiotica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Aril	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7237	Xanthostemon oppositifolius	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28409	Lens phaseoloides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8532	Helipterum tenellum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6113	Piper pedicellosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5162	Comaster multifida	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19928	Lachnoanaerobaculum saburreum	Species	Lachnospiraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4539	Ipomoea cristulata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO490	Lophozonia menziesii	Species	Nothofagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17811	Cephalonoplos segetum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5746	Pancratium trianthum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7393	Esenbeckia nesiotica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5334	Rhodotypos scandens	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2665	Andinobates fulguritus	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5241	Myristica fragrans	Species	Myristicaceae	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 NPC141529 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	19269
0.1-0.2	24060
0.2-0.3	5728
0.3-0.4	676
0.4-0.5	116
0.5-0.6	6
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	0

Similarity Score	Similarity Level	Natural Product ID
0.6102	Remote Similarity	NPC203831
0.6034	Remote Similarity	NPC210674
0.6034	Remote Similarity	NPC104934
0.5893	Remote Similarity	NPC307042
0.54	Remote Similarity	NPC257124
0.5323	Remote Similarity	NPC485477
0.5263	Remote Similarity	NPC604372
0.5091	Remote Similarity	NPC209567
0.5077	Remote Similarity	NPC470095

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC141529 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4009
0.1-0.2	4910
0.2-0.3	222
0.3-0.4	8
0.4-0.5	0
0.5-0.6	1
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
0.54	Remote Similarity	NPD228	Phase 0

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