NPASS Compound

Natural Product: NPC190629

Natural Product ID	NPC190629
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(+)-Erythro-(7S,8R)-Delta8'-7-Hydroxy-3,4,3',5'-Tetramethoxy-8-O-4'-Neolignan
IUPAC Name	(1S,2R)-1-(3,4-dimethoxyphenyl)-2-(2,6-dimethoxy-4-prop-2-enylphenoxy)propan-1-ol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL463097
PubChem CID	44566598
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

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 7.2726 -0.2741 1.6098 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5821 -0.5708 0.5190 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4135 -1.4949 0.6610 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1948 -0.7737 0.2148 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4807 -0.0602 1.1460 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3224 0.6438 0.7965 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6230 1.3563 1.7610 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1039 1.3519 3.0823 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9259 0.5919 -0.5230 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6285 -0.1194 -1.4774 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7608 -0.7951 -1.0855 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2378 -0.1767 -2.8038 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9344 -0.8909 -3.7874 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7816 1.2773 -0.9056 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5106 0.6992 -0.9197 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4200 1.5258 -0.0766 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7578 0.9838 0.1251 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7181 1.7411 0.7547 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0101 1.2436 0.9574 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3193 -0.0249 0.5176 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3649 -0.8047 -0.1197 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0989 -0.2663 -0.2968 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7214 -2.0750 -0.5450 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8593 -2.9628 -1.1984 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5928 -0.5091 0.7200 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5594 0.2889 1.3687 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4755 2.8564 -0.5765 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9357 0.6814 -2.3804 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1320 0.3964 1.5487 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0287 -0.6655 2.5745 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8361 -0.1728 -0.4403 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2646 -1.8023 1.7126 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5963 -2.4092 0.0613 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7926 -0.0181 2.1895 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1476 1.7552 3.1635 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4908 2.0129 3.7335 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1451 0.3148 3.4327 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3657 -1.3778 -1.7849 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0244 -0.7217 -3.7650 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5820 -0.5406 -4.7852 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7050 -1.9856 -3.6875 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4603 -0.3238 -0.5015 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9448 1.6434 0.9294 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5226 2.7398 1.1163 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7408 1.8691 1.4573 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3728 -0.8778 -0.7913 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9780 -2.9567 -2.3093 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8270 -2.8637 -0.8652 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1854 -4.0001 -0.8924 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4727 -0.3294 1.5090 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8238 1.2018 0.8312 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2061 0.5902 2.3914 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4230 3.0548 -0.7849 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8125 -0.3596 -2.7302 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2888 1.3152 -3.0207 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9704 1.0682 -2.5162 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 1 0 7 8 1 0 6 9 2 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 9 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 1 0 20 25 1 0 25 26 1 0 16 27 1 0 15 28 1 0 11 4 1 0 22 17 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 8 35 1 0 8 36 1 0 8 37 1 0 11 38 1 0 13 39 1 0 13 40 1 0 13 41 1 0 15 42 1 1 16 43 1 1 18 44 1 0 19 45 1 0 22 46 1 0 24 47 1 0 24 48 1 0 24 49 1 0 26 50 1 0 26 51 1 0 26 52 1 0 27 53 1 0 28 54 1 0 28 55 1 0 28 56 1 0 M END

Standard InCHIKey	IQBXVNSNERBTIG-SPLOXXLWSA-N
Standard InCHI	InChI=1S/C22H28O6/c1-7-8-15-11-19(26-5)22(20(12-15)27-6)28-14(2)21(23)16-9-10-17(24-3)18(13-16)25-4/h7,9-14,21,23H,1,8H2,2-6H3/t14-,21-/m1/s1
SMILES	C=CCc1cc(OC)c(c(c1)OC)O[C@@H]([C@H](c1ccc(c(c1)OC)OC)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	388.19	Volume:	406.241 ? Van der Waals volume.
Dense:	0.956	LogP:	2.724 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.821 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.887 ? 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:	0.622	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.11	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:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.297	Fluc inhibitor:	0.107 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.214 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.317	Promiscuous compounds:	0.048

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.623	MDCK Permeability:	-4.763
Pgp-inhibitor:	0.463	Pgp-substrate:	0.002
PAMPA:	0.004 ? 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%):	0.105	30% Bioavailability (F30%):	0.233
50% Bioavailability (F50%):	0.774

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114	MRP1:	0.889
Plasma Protein Binding (PPB):	85.225%	Volume Distribution (VD):	0.318
Fu:	15.255% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.712
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.674
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.009
CYP2C9-inhibitor:	0.435	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.997	CYP2D6-substrate:	0.861
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.956
CYP2B6-substrate:	0.016	CYP2C8-inhibitor:	1.0
HLM stability:	0.211 ? 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):

9.116

Half-life (T1/2):

1.996

ADMET: Toxicity

hERG Blockers:	0.221	hERG Blockers (10um):	0.659
Human Hepatotoxicity (H-HT):	0.628	Drug-induced Liver Injury (DILI):	0.516
AMES Toxicity:	0.347	Rat Oral Acute Toxicity:	0.39
Maximum Recommended Daily Dose:	0.481	Skin Sensitization:	0.658
Carcinogencity:	0.486	Eye Corrosion:	0.029
Eye Irritation:	0.634	Respiratory Toxicity:	0.682
Drug-induced Neurotoxicity:	0.8	Ototoxicity:	0.503
Hematotoxicity:	0.242	Drug-induced Nephrotoxicity:	0.341
Genotoxicity:	0.417	RPMI-8226 Immunitoxicity:	0.099
A549 Cytotoxicity:	0.174	Hek293 Cytotoxicity:	0.55
BCF:	1.154 ? 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:	3.432 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.748 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.941 ? 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

Activity Type	# Activity
EC50	1
MIC	5
IC50	1

Activity Type	# Activity
Individual protein	1
Cell line	1
Organism	5

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5259	Individual protein	Transient receptor potential cation channel subfamily M member 8	Homo sapiens	EC50	>	10000.0	nM	PMID[28740604]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[21978676]
NPT1819	Organism	Microsporum canis	Arthroderma otae	MIC	=	150.0	ug.mL-1	PMID[9249968]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	=	50.0	ug.mL-1	PMID[9249968]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	150.0	ug.mL-1	PMID[9249968]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	80.0	ug.mL-1	PMID[9249968]
NPT328	Organism	Epidermophyton floccosum	Epidermophyton floccosum	MIC	=	40.0	ug.mL-1	PMID[9249968]

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 NPC190629 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	16449
0.1-0.2	29467
0.2-0.3	3686
0.3-0.4	175
0.4-0.5	44
0.5-0.6	27
0.6-0.7	3
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.82	Intermediate Similarity	NPC484134
0.8	Intermediate Similarity	NPC202582
0.8	Intermediate Similarity	NPC243749
0.7	Intermediate Similarity	NPC470258
0.6981	Remote Similarity	NPC203831
0.6923	Remote Similarity	NPC25695
0.6863	Remote Similarity	NPC354196
0.5849	Remote Similarity	NPC94276
0.5849	Remote Similarity	NPC109822
0.5849	Remote Similarity	NPC605984
0.5818	Remote Similarity	NPC3439
0.5818	Remote Similarity	NPC285339
0.5789	Remote Similarity	NPC471719
0.5556	Remote Similarity	NPC473090
0.5455	Remote Similarity	NPC273295
0.5455	Remote Similarity	NPC292792
0.5455	Remote Similarity	NPC222004
0.5455	Remote Similarity	NPC602870
0.5439	Remote Similarity	NPC210674
0.5439	Remote Similarity	NPC260842
0.5439	Remote Similarity	NPC93783
0.5439	Remote Similarity	NPC104934
0.5439	Remote Similarity	NPC320380
0.5385	Remote Similarity	NPC218856
0.5385	Remote Similarity	NPC210623
0.5385	Remote Similarity	NPC226788
0.5263	Remote Similarity	NPC35932
0.5254	Remote Similarity	NPC469613
0.5254	Remote Similarity	NPC30043
0.5254	Remote Similarity	NPC469625
0.52	Remote Similarity	NPC261661
0.52	Remote Similarity	NPC601166
0.5179	Remote Similarity	NPC473091
0.5094	Remote Similarity	NPC28326

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC190629 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3544
0.1-0.2	5300
0.2-0.3	292
0.3-0.4	13
0.4-0.5	1
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