NPASS Compound

Natural Product: NPC151719

Natural Product ID	NPC151719
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(Z)-Tricos-9-Ene
IUPAC Name	(Z)-tricos-9-ene
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1894305
PubChem CID	5365075
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002837] Hydrocarbons [CHEMONTID:0004475] Unsaturated hydrocarbons [CHEMONTID:0004476] Unsaturated aliphatic hydrocarbons

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 69 68 0 0 0 0 0 0 0 0999 V2000 -9.3801 -0.7560 -1.2311 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4346 -1.8304 -0.7622 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0524 -1.1131 -0.6019 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2872 -0.0568 0.3987 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2232 0.8136 0.8776 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4609 1.7184 0.0191 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6467 1.0632 -1.0422 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6438 0.0706 -0.4335 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7250 0.7468 0.4827 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4288 0.7817 0.3233 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7269 0.1518 -0.7894 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2424 -0.8900 -0.2516 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2607 -0.2510 0.6626 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1755 -1.3894 1.1253 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2421 -0.8714 2.0550 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1185 0.1810 1.3800 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1641 0.6650 2.3356 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1213 1.6425 1.8354 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2176 1.4223 0.9279 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2096 0.7756 -0.3726 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0502 -0.7139 -0.4432 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0520 -1.1623 -1.9185 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8931 -0.4647 -2.5896 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1037 -1.1708 -1.9615 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8619 0.0779 -1.7590 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9889 -0.3376 -0.3912 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6983 -2.1462 0.2515 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3355 -2.6300 -1.4985 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3115 -1.8458 -0.2895 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8569 -0.7972 -1.6398 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1852 0.5705 0.1074 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6950 -0.6030 1.3245 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7093 1.4835 1.6876 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5151 0.2088 1.5445 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0953 2.5140 -0.4689 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7136 2.3301 0.6317 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9839 1.8951 -1.5065 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1708 0.5563 -1.8500 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2945 -0.6338 0.1553 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1849 -0.5287 -1.2318 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1641 1.2517 1.3581 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8200 1.3176 1.0605 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3228 -0.3376 -1.5531 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0661 0.9108 -1.3268 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7677 -1.3930 -1.1062 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2923 -1.6620 0.3389 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7359 0.1488 1.5450 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8112 0.4773 0.0690 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6949 -1.8161 0.2426 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5953 -2.1600 1.6699 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8507 -1.7045 2.4406 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7314 -0.4056 2.9408 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3725 1.0512 1.2345 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3878 -0.1309 0.4020 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6374 -0.1947 2.8931 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5752 1.1746 3.1733 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5756 2.2000 2.7493 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4877 2.5162 1.4176 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1430 0.9868 1.4869 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6679 2.4909 0.7338 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2347 0.9713 -0.8466 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5226 1.2806 -1.1170 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0162 -1.1859 -0.0490 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2002 -1.1692 0.0297 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9945 -0.9222 -2.4132 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8089 -2.2413 -1.8927 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2192 0.5210 -2.9815 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0698 -0.3215 -1.8730 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5319 -1.1315 -3.4022 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 1 24 1 0 1 25 1 0 1 26 1 0 2 27 1 0 2 28 1 0 3 29 1 0 3 30 1 0 4 31 1 0 4 32 1 0 5 33 1 0 5 34 1 0 6 35 1 0 6 36 1 0 7 37 1 0 7 38 1 0 8 39 1 0 8 40 1 0 9 41 1 0 10 42 1 0 11 43 1 0 11 44 1 0 12 45 1 0 12 46 1 0 13 47 1 0 13 48 1 0 14 49 1 0 14 50 1 0 15 51 1 0 15 52 1 0 16 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 18 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 20 61 1 0 20 62 1 0 21 63 1 0 21 64 1 0 22 65 1 0 22 66 1 0 23 67 1 0 23 68 1 0 23 69 1 0 M END

Standard InCHIKey	IGOWHGRNPLFNDJ-ZPHPHTNESA-N
Standard InCHI	InChI=1S/C23H46/c1-3-5-7-9-11-13-15-17-19-21-23-22-20-18-16-14-12-10-8-6-4-2/h17,19H,3-16,18,20-23H2,1-2H3/b19-17-
SMILES	CCCCCCCC/C=CCCCCCCCCCCCCC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	322.36	Volume:	403.728 ? Van der Waals volume.
Dense:	0.798	LogP:	10.255 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.208 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-10.194 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	19.0	Rigid Bonds:	1.0
TPSA:	0.0 ? Topological Polar Surface Area.	H-Bond Acceptor:	0.0
H-Bond Donor:	0.0	Rings:	0.0
Heavy Atoms:	0.0

MedChem Properties

QED Drug-Likeness Score:	0.164	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	1.69	Fsp³:	0.913
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:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.659	Fluc inhibitor:	0.208 ? 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:	0.007 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.997	Promiscuous compounds:	0.32

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.052	MDCK Permeability:	-4.844
Pgp-inhibitor:	0.198	Pgp-substrate:	0.001
PAMPA:	0.0 ? 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):	0.57
20% Bioavailability (F20%):	0.95	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019	MRP1:	0.994
Plasma Protein Binding (PPB):	100.13%	Volume Distribution (VD):	1.379
Fu:	0.175% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.05
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.981
BSEP inhibitor:	0.996

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.574
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.506	CYP2C8-inhibitor:	1.0
HLM stability:	0.003 ? 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):

5.069

Half-life (T1/2):

0.806

ADMET: Toxicity

hERG Blockers:	0.723	hERG Blockers (10um):	0.932
Human Hepatotoxicity (H-HT):	0.282	Drug-induced Liver Injury (DILI):	0.006
AMES Toxicity:	0.057	Rat Oral Acute Toxicity:	0.131
Maximum Recommended Daily Dose:	0.306	Skin Sensitization:	1.0
Carcinogencity:	0.106	Eye Corrosion:	0.999
Eye Irritation:	0.997	Respiratory Toxicity:	0.946
Drug-induced Neurotoxicity:	0.007	Ototoxicity:	0.102
Hematotoxicity:	0.028	Drug-induced Nephrotoxicity:	0.207
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.058
A549 Cytotoxicity:	0.976	Hek293 Cytotoxicity:	0.478
BCF:	0.661 ? 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:	5.388 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.225 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.014 ? 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
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[15387656]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	Niigata City, Niigata Province, Japan	2000-Nov	PMID[15730243]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	ripe fruit	n.a.	PMID[16205005]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933868]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253842]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	Niigata City, Niigata Province, Japan	2001-NOV	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	n.a.	n.a.	PMID[17595134]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18409045]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[19926279]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[2092947]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	berry	n.a.	n.a.	PMID[21216145]
NPO29279	Aralia elata	Species	Araliaceae	Eukaryota	bark	n.a.	n.a.	PMID[21889336]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24290061]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24968750]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25152999]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	stems-leaves	n.a.	n.a.	PMID[26420067]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[27914541]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[28345906]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29693393]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[33253570]
NPO30289	Rosa damascena	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33861759]
NPO54179	Magnolia sumatrana var. glauca	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34328033]
NPO46827	Alhagi mannifera	Genus	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34384010]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36362399]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[3701342]
NPO30289	Rosa damascena	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38005389]
NPO29279	Aralia elata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39204353]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	Leaves; Stems	n.a.	n.a.	PMID[9214727]
NPO30289	Rosa damascena	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8714	Elaeocarpus mastersii	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29279	Aralia elata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30289	Rosa damascena	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29279	Aralia elata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29279	Aralia elata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29279	Aralia elata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29279	Aralia elata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8714	Elaeocarpus mastersii	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18932	Melia azedarach	Species	Meliaceae	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
NPO29279	Aralia elata	Oil	n.a.	2.28	n.a.	n.a.	%	PMID[39204353]
NPO30289	Rosa damascena	Oil	n.a.	0.61Â±0.00	n.a.	n.a.	%	PMID[33861759]
NPO30289	Rosa damascena	Oil	n.a.	0.92Â±0.00	n.a.	n.a.	%	PMID[33861759]
NPO30289	Rosa damascena	Oil	n.a.	0.82Â±0.00	n.a.	n.a.	%	PMID[33861759]
NPO46827	Alhagi mannifera	n.a.	n.a.	3.37	n.a.	n.a.	%	PMID[34384010]
NPO54179	Magnolia sumatrana var. glauca	Oil	Branches	0.15	n.a.	n.a.	%	PMID[34328033]

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
Potency	3

Activity Type	# Activity
Individual protein	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT198	Individual protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	1.4	nM	PubChem BioAssay data set
NPT540	Individual protein	Bile acid receptor FXR	Homo sapiens	Potency	n.a.	1.0	nM	PubChem BioAssay data set
NPT46	Individual protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	n.a.	44668.4	nM	PubChem BioAssay data set

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
-	Rattus norvegicus	LD50	>	23070.0	mg/kg	ToxVal
-	Oryctolagus cuniculus	LD50	>	2025.0	mg/kg	ToxVal

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 NPC151719 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	43591
0.1-0.2	4938
0.2-0.3	890
0.3-0.4	310
0.4-0.5	65
0.5-0.6	28
0.6-0.7	23
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
0.6842	Remote Similarity	NPC182392
0.65	Remote Similarity	NPC44363
0.65	Remote Similarity	NPC125129
0.65	Remote Similarity	NPC110234
0.65	Remote Similarity	NPC76976
0.65	Remote Similarity	NPC163751
0.625	Remote Similarity	NPC266539
0.625	Remote Similarity	NPC179103
0.625	Remote Similarity	NPC88325
0.625	Remote Similarity	NPC287191
0.625	Remote Similarity	NPC31891
0.625	Remote Similarity	NPC266144
0.625	Remote Similarity	NPC76765
0.6	Remote Similarity	NPC34671
0.6	Remote Similarity	NPC11487
0.6	Remote Similarity	NPC67920
0.6	Remote Similarity	NPC239754
0.6	Remote Similarity	NPC252978
0.6	Remote Similarity	NPC33489
0.6	Remote Similarity	NPC298710
0.6	Remote Similarity	NPC311716
0.6	Remote Similarity	NPC217923
0.6	Remote Similarity	NPC287397
0.5909	Remote Similarity	NPC261571
0.5909	Remote Similarity	NPC188341
0.55	Remote Similarity	NPC33761
0.5417	Remote Similarity	NPC474642
0.5417	Remote Similarity	NPC473913
0.5417	Remote Similarity	NPC309606
0.5385	Remote Similarity	NPC273385
0.5385	Remote Similarity	NPC278711
0.5385	Remote Similarity	NPC98925
0.5385	Remote Similarity	NPC64370
0.5385	Remote Similarity	NPC82648
0.5385	Remote Similarity	NPC227986
0.5385	Remote Similarity	NPC239406
0.5385	Remote Similarity	NPC77249
0.5385	Remote Similarity	NPC26974
0.5385	Remote Similarity	NPC136996
0.5385	Remote Similarity	NPC302327
0.5385	Remote Similarity	NPC154477
0.5385	Remote Similarity	NPC89422
0.5385	Remote Similarity	NPC26229
0.5333	Remote Similarity	NPC178306
0.5217	Remote Similarity	NPC15934
0.5217	Remote Similarity	NPC155880
0.5217	Remote Similarity	NPC609384
0.52	Remote Similarity	NPC49494
0.52	Remote Similarity	NPC262968
0.52	Remote Similarity	NPC600749
0.52	Remote Similarity	NPC601019

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC151719 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8570
0.1-0.2	509
0.2-0.3	50
0.3-0.4	11
0.4-0.5	6
0.5-0.6	2
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
0.52	Remote Similarity	NPD28	Approved
0.52	Remote Similarity	NPD29	Phase 4

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