NPASS Compound

Natural Product: NPC209431

Natural Product ID	NPC209431
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(4S)-4-Prop-1-En-2-Ylcyclohexene-1-Carbaldehyde
IUPAC Name	(4S)-4-prop-1-en-2-ylcyclohexene-1-carbaldehyde
Synonyms	S(-)-Perillaldehyde
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL442913
PubChem CID	2724159
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001401] Menthane monoterpenoids

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 25 25 0 0 0 0 0 0 0 0999 V2000 4.2387 0.8024 1.2411 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6488 -0.0122 0.5175 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2310 0.1844 0.2002 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5801 1.2278 0.6834 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1383 1.3457 0.3065 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5035 0.0170 0.6501 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1728 -1.1378 -0.0209 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4864 -0.7655 -0.6615 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9641 0.0919 0.3647 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5129 1.1381 -0.2231 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8436 -1.0451 0.7508 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1552 -0.8802 0.1045 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0618 1.9722 1.3265 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3039 2.1517 0.9260 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0322 1.5656 -0.7692 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3810 -0.1156 1.7451 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3880 -1.9677 0.7143 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4850 -1.5822 -0.7881 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1001 -1.6881 -0.7265 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3678 -0.3810 -1.6960 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9438 2.0036 -0.5342 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5735 1.1450 -0.4079 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2146 -1.9629 0.7784 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2386 -0.8823 1.7711 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6364 -1.2245 0.0070 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 1 0 6 7 1 0 7 8 1 0 6 9 1 0 9 10 2 0 9 11 1 0 8 3 1 0 2 12 1 0 4 13 1 0 5 14 1 0 5 15 1 0 6 16 1 1 7 17 1 0 7 18 1 0 8 19 1 0 8 20 1 0 10 21 1 0 10 22 1 0 11 23 1 0 11 24 1 0 11 25 1 0 M END

Standard InCHIKey	RUMOYJJNUMEFDD-SNVBAGLBSA-N
Standard InCHI	InChI=1S/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,7,10H,1,4-6H2,2H3/t10-/m1/s1
SMILES	O=CC1=CC[C@H](CC1)C(=C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	150.1	Volume:	173.841 ? Van der Waals volume.
Dense:	0.863	LogP:	2.665 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.523 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.185 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	8.0
TPSA:	17.07 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	0.0	Rings:	1.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.436	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.684	Fsp³:	0.5
MCE-18:	15.2 ? 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:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.108	Fluc inhibitor:	0.109 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	1.0	Promiscuous compounds:	0.151

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.548	MDCK Permeability:	-4.517
Pgp-inhibitor:	0.515	Pgp-substrate:	0.051
PAMPA:	0.178 ? 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):	0.013
20% Bioavailability (F20%):	0.058	30% Bioavailability (F30%):	0.194
50% Bioavailability (F50%):	0.217

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.887	MRP1:	0.629
Plasma Protein Binding (PPB):	83.808%	Volume Distribution (VD):	0.346
Fu:	15.464% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.205
OATP1B3 inhibitor:	0.415	BCRP inhibitor:	0.196
BSEP inhibitor:	0.568

ADMET: Metabolism

CYP1A2-inhibitor:	0.066	CYP1A2-substrate:	0.068
CYP2C19-inhibitor:	0.968	CYP2C19-substrate:	0.011
CYP2C9-inhibitor:	0.752	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.179	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.245	CYP3A4-substrate:	0.155
CYP2B6-substrate:	0.186	CYP2C8-inhibitor:	0.558
HLM stability:	0.103 ? 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):

7.896

Half-life (T1/2):

1.425

ADMET: Toxicity

hERG Blockers:	0.083	hERG Blockers (10um):	0.468
Human Hepatotoxicity (H-HT):	0.438	Drug-induced Liver Injury (DILI):	0.309
AMES Toxicity:	0.638	Rat Oral Acute Toxicity:	0.448
Maximum Recommended Daily Dose:	0.453	Skin Sensitization:	0.744
Carcinogencity:	0.668	Eye Corrosion:	0.988
Eye Irritation:	0.996	Respiratory Toxicity:	0.709
Drug-induced Neurotoxicity:	0.393	Ototoxicity:	0.192
Hematotoxicity:	0.255	Drug-induced Nephrotoxicity:	0.198
Genotoxicity:	0.248	RPMI-8226 Immunitoxicity:	0.055
A549 Cytotoxicity:	0.148	Hek293 Cytotoxicity:	0.176
BCF:	1.128 ? 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:	3.663 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.235 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.796 ? 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
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2009.03.042]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.3136/fstr.15.499]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB10.140]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB2010.000-3252]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16038540]
NPO14358	Rhodobacter sphaeroides	Species	Rhodobacteraceae	Bacteria	n.a.	n.a.	n.a.	PMID[1612412]
NPO8068	Blumea mollis	Species	Asteraceae	Eukaryota	n.a.	leaf	n.a.	PMID[18566831]
NPO14162	Chlorophytum borivilianum	Species	Asparagaceae	Eukaryota	roots	n.a.	n.a.	PMID[19128156]
NPO7016	Gardenia tubifera	Species	Rubiaceae	Eukaryota	exudate	n.a.	n.a.	PMID[20028108]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20674349]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[21428274]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21428274]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22272932]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	Tongxiang, China	n.a.	PMID[24621197]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25320841]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26169681]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28248102]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34771092]
NPO1539	Artemisia giraldii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36364129]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37049761]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37656744]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38786901]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14358	Rhodobacter sphaeroides	Species	Rhodobacteraceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13467	Anarsia lineatella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14057	Apollonias barbujana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4004	Aquilegia ecalcarata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10550	Artemisia hanseniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8068	Blumea mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13766	Ceanothus velutinus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14162	Chlorophytum borivilianum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12509	Dipterocarpus dyeri	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7016	Gardenia tubifera	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16703	Isodon lophanthoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO205	Lasianthus fordii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11998	Ledebouria socialis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO746	Panax innovans	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5191	Penicillium cinerascens	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4671	Persea mexicana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8892	Sordaria araneosa	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1539	Artemisia giraldii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16703	Isodon lophanthoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4004	Aquilegia ecalcarata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5191	Penicillium cinerascens	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1539	Artemisia giraldii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4671	Persea mexicana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8892	Sordaria araneosa	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14358	Rhodobacter sphaeroides	Species	Rhodobacteraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13766	Ceanothus velutinus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4004	Aquilegia ecalcarata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14057	Apollonias barbujana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16703	Isodon lophanthoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11998	Ledebouria socialis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO746	Panax innovans	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10550	Artemisia hanseniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13467	Anarsia lineatella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14162	Chlorophytum borivilianum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12509	Dipterocarpus dyeri	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7016	Gardenia tubifera	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO205	Lasianthus fordii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8068	Blumea mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10082	Citrus unshiu	Species	Rutaceae	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
NPO1539	Artemisia giraldii	Oil	n.a.	0.14	n.a.	n.a.	%	PMID[36364129]

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	7

Activity Type	# Activity
Individual protein	1
Others	6

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	61130.6	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	Potency	n.a.	138	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	54482.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	48557.7	nM	PubChem BioAssay data set

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 NPC209431 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	24924
0.1-0.2	23159
0.2-0.3	1672
0.3-0.4	86
0.4-0.5	10
0.5-0.6	3
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	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC100809
0.6	Remote Similarity	NPC190810
0.6	Remote Similarity	NPC34764
0.6	Remote Similarity	NPC76145
0.5172	Remote Similarity	NPC148216
0.5172	Remote Similarity	NPC130209
0.5172	Remote Similarity	NPC148163

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC209431 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7256
0.1-0.2	1833
0.2-0.3	58
0.3-0.4	1
0.4-0.5	0
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	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6	Remote Similarity	NPD319	Phase 2
0.5172	Remote Similarity	NPD342	Phase 1

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