NPASS Compound

Natural Product: NPC26062

Natural Product ID	NPC26062
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OJISWRZIEWCUBN-KWBDAJKESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5365865
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001357] Acyclic diterpenoids

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 55 54 0 0 0 0 0 0 0 0999 V2000 8.6495 1.1434 0.4731 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3889 0.3630 0.3627 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4985 0.7440 -0.5367 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2309 0.0074 -0.6902 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1028 0.9925 -0.4130 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7974 0.3176 -0.5500 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9580 0.2535 0.4714 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6496 -0.4307 0.3107 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4655 0.5540 0.5796 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7869 -0.1413 0.4161 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6603 0.2787 -0.4828 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9750 -0.3734 -0.6812 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1233 0.5872 -0.4353 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4355 -0.0514 -0.6272 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3471 -0.1551 0.3189 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2116 0.3379 1.6982 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2052 1.2924 2.0067 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7811 -0.6276 -1.9849 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0909 -1.3191 1.2939 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4211 -0.2960 -1.8470 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1593 -0.8058 1.2472 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3397 0.7633 -0.3269 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4216 2.2335 0.3069 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0578 0.9892 1.4898 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6567 1.6034 -1.1939 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2039 -0.8045 0.0580 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1569 -0.4314 -1.7058 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2224 1.3503 0.6076 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1811 1.8380 -1.1114 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2133 0.6944 1.4251 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5574 -1.2285 1.1046 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5494 -0.9487 -0.6450 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3680 0.8822 1.6371 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4080 1.4607 -0.0370 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3994 1.1277 -1.0904 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0931 -0.7420 -1.7324 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0180 -1.2533 -0.0378 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0891 1.4224 -1.2078 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9833 1.0709 0.5133 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2938 -0.6561 0.0489 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4282 -0.5013 2.4092 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2101 0.6734 1.9329 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2809 1.8654 1.1816 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9464 -1.1416 -2.4558 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1590 0.1688 -2.6523 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5950 -1.3714 -1.8643 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0165 -2.2769 0.7472 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0899 -1.1796 1.7771 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3613 -1.3548 2.1211 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2044 -1.3840 -1.7547 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2655 -0.2173 -2.5609 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5649 0.2484 -2.3230 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1714 -1.7215 0.6114 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2211 -0.7186 1.8311 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9785 -0.9007 1.9659 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 14 18 1 0 10 19 1 0 6 20 1 0 2 21 1 0 1 22 1 0 1 23 1 0 1 24 1 0 3 25 1 0 4 26 1 0 4 27 1 0 5 28 1 0 5 29 1 0 7 30 1 0 8 31 1 0 8 32 1 0 9 33 1 0 9 34 1 0 11 35 1 0 12 36 1 0 12 37 1 0 13 38 1 0 13 39 1 0 15 40 1 0 16 41 1 0 16 42 1 0 17 43 1 0 18 44 1 0 18 45 1 0 18 46 1 0 19 47 1 0 19 48 1 0 19 49 1 0 20 50 1 0 20 51 1 0 20 52 1 0 21 53 1 0 21 54 1 0 21 55 1 0 M END

Standard InCHIKey	OJISWRZIEWCUBN-KWBDAJKESA-N
Standard InCHI	InChI=1S/C20H34O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h9,11,13,15,21H,6-8,10,12,14,16H2,1-5H3/b18-11+,19-13+,20-15-
SMILES	CC(=CCC/C(=C/CC/C(=C/CC/C(=CCO)/C)/C)/C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	290.26	Volume:	352.721 ? Van der Waals volume.
Dense:	0.823	LogP:	7.044 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.251 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.632 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	4.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	0.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.48	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.952	Fsp³:	0.6
MCE-18:	0.0 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.395	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.967	Promiscuous compounds:	0.111

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.469	MDCK Permeability:	-4.752
Pgp-inhibitor:	0.999	Pgp-substrate:	0.001
PAMPA:	0.002 ? 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):	0.038
20% Bioavailability (F20%):	0.003	30% Bioavailability (F30%):	0.005
50% Bioavailability (F50%):	0.415

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014	MRP1:	0.973
Plasma Protein Binding (PPB):	89.68%	Volume Distribution (VD):	-0.305
Fu:	8.236% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.0
BSEP inhibitor:	0.991

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.006
CYP2C19-inhibitor:	0.994	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.895	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.985	CYP2D6-substrate:	0.721
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.172
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.214
HLM stability:	0.96 ? 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):

9.788

Half-life (T1/2):

0.983

ADMET: Toxicity

hERG Blockers:	0.062	hERG Blockers (10um):	0.393
Human Hepatotoxicity (H-HT):	0.831	Drug-induced Liver Injury (DILI):	0.019
AMES Toxicity:	0.098	Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.052	Skin Sensitization:	0.999
Carcinogencity:	0.122	Eye Corrosion:	0.438
Eye Irritation:	0.992	Respiratory Toxicity:	0.937
Drug-induced Neurotoxicity:	0.419	Ototoxicity:	0.447
Hematotoxicity:	0.246	Drug-induced Nephrotoxicity:	0.378
Genotoxicity:	0.004	RPMI-8226 Immunitoxicity:	0.043
A549 Cytotoxicity:	0.044	Hek293 Cytotoxicity:	0.04
BCF:	2.376 ? 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:	5.288 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.621 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.464 ? 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
NPO14864	Clerodendrum cyrtophyllum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473423]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575948]
NPO12347	Pseudomonas syringae	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14714872]
NPO15548	Sinularia leptoclados	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724859]
NPO13549	Otanthus maritimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39715713]
NPO3974	Ferula gummosa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20070	Crinum stuhlmannii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4699	Dracaena ombet	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11683	Crotalaria mitchellii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6367	Cortinarius viola	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14864	Clerodendrum cyrtophyllum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26712	Cladrastis kentukea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4503	Bryonopsis laciniosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14191	Berkheya rhapontica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11151	Arnebia decumbens	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19872	Achillea magnifica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14989	Acanthothamnus aphyllus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4518.1	Saccharothrix mutabilis subsp. capreolus	Subspecies	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22084	Stypandra imbricata	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12121	Streptomyces naraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15548	Sinularia leptoclados	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1027	Scrophularia leucoclada	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13320	Glycosmis puberula	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5469	Pseudoxandra sclerocarpa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12993	Polypodium vulgare	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15066	Iridaea membranacea	Species	Gigartinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13549	Otanthus maritimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11505	Nigella aristata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7042	Myrica arborea	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12539	Lissoclinum japonicum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8392	Iryanthera polyneura	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9338	Polygala aureocauda	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12993	Polypodium vulgare	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12993	Polypodium vulgare	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7042	Myrica arborea	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8392	Iryanthera polyneura	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12993	Polypodium vulgare	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22084	Stypandra imbricata	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1027	Scrophularia leucoclada	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15066	Iridaea membranacea	Species	Gigartinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11505	Nigella aristata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14989	Acanthothamnus aphyllus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12121	Streptomyces naraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12993	Polypodium vulgare	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12347	Pseudomonas syringae	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11683	Crotalaria mitchellii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14864	Clerodendrum cyrtophyllum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19872	Achillea magnifica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8392	Iryanthera polyneura	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4699	Dracaena ombet	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15548	Sinularia leptoclados	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11151	Arnebia decumbens	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4503	Bryonopsis laciniosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20070	Crinum stuhlmannii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12539	Lissoclinum japonicum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5469	Pseudoxandra sclerocarpa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7042	Myrica arborea	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4518.1	Saccharothrix mutabilis subsp. capreolus	Subspecies	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6367	Cortinarius viola	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13549	Otanthus maritimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26712	Cladrastis kentukea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3974	Ferula gummosa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13320	Glycosmis puberula	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14191	Berkheya rhapontica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9338	Polygala aureocauda	Species	Polygalaceae	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 NPC26062 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	30292
0.1-0.2	17847
0.2-0.3	1401
0.3-0.4	233
0.4-0.5	56
0.5-0.6	12
0.6-0.7	6
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC29091
1.0	High Similarity	NPC103213
1.0	High Similarity	NPC300623
1.0	High Similarity	NPC213538
1.0	High Similarity	NPC269823
1.0	High Similarity	NPC39222
1.0	High Similarity	NPC9860
0.9091	High Similarity	NPC182840
0.9091	High Similarity	NPC255042
0.8148	Intermediate Similarity	NPC140501
0.7692	Intermediate Similarity	NPC116934
0.7	Intermediate Similarity	NPC604226
0.6774	Remote Similarity	NPC138935
0.6774	Remote Similarity	NPC601961
0.6522	Remote Similarity	NPC123965
0.6522	Remote Similarity	NPC115959
0.625	Remote Similarity	NPC474496
0.6	Remote Similarity	NPC122239
0.5926	Remote Similarity	NPC160628
0.5667	Remote Similarity	NPC67761
0.5667	Remote Similarity	NPC209279
0.5667	Remote Similarity	NPC194586
0.5667	Remote Similarity	NPC108494
0.5667	Remote Similarity	NPC51758
0.5556	Remote Similarity	NPC474495
0.5556	Remote Similarity	NPC305759
0.5556	Remote Similarity	NPC473672
0.5333	Remote Similarity	NPC128280
0.5172	Remote Similarity	NPC185839
0.5172	Remote Similarity	NPC180840

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC26062 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8218
0.1-0.2	901
0.2-0.3	19
0.3-0.4	6
0.4-0.5	4
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8148	Intermediate Similarity	NPD4265	Phase 2
0.5172	Remote Similarity	NPD5783	Phase 3

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