NPASS Compound

Natural Product: NPC291789

Natural Product ID	NPC291789
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Pinosylvin
IUPAC Name	5-[(E)-2-phenylethenyl]benzene-1,3-diol
Synonyms	Pinosylvin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL101506
PubChem CID	5280457
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

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 28 29 0 0 0 0 0 0 0 0999 V2000 -4.9710 -0.3254 0.3565 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5241 0.6619 -0.4916 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1684 0.8511 -0.6582 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2116 0.0741 0.0053 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6991 -0.8937 0.8369 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0676 -1.1074 1.0244 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8007 0.3330 -0.2212 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1481 -0.3527 0.3639 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5688 -0.1263 0.1653 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5038 -0.9101 0.8345 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8566 -0.7145 0.6626 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3145 0.2751 -0.1876 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4265 1.0699 -0.8664 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0596 0.8408 -0.6657 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8878 2.0583 -1.7156 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7746 -1.5227 1.3529 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0522 -0.4724 0.4860 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2593 1.2737 -1.0141 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8078 1.6283 -1.3259 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0511 -1.5346 1.3846 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4387 -1.8797 1.6880 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5050 1.1351 -0.9100 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1381 -1.1358 1.0364 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1188 -1.6836 1.4992 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3927 0.3821 -0.2827 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4202 1.5023 -1.2311 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7590 3.0417 -1.4902 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 -2.4680 1.5464 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 2 0 4 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 11 16 1 0 6 1 1 0 14 9 1 0 1 17 1 0 2 18 1 0 3 19 1 0 5 20 1 0 6 21 1 0 7 22 1 0 8 23 1 0 10 24 1 0 12 25 1 0 14 26 1 0 15 27 1 0 16 28 1 0 M END

Standard InCHIKey	YCVPRTHEGLPYPB-VOTSOKGWSA-N
Standard InCHI	InChI=1S/C14H12O2/c15-13-8-12(9-14(16)10-13)7-6-11-4-2-1-3-5-11/h1-10,15-16H/b7-6+
SMILES	c1ccc(cc1)/C=C/c1cc(cc(c1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	212.08	Volume:	232.713 ? Van der Waals volume.
Dense:	0.911	LogP:	3.713 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.369 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.865 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	13.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.75	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	1.944	Fsp³:	0.0
MCE-18:	10.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.682	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.016 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.12 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.998	Promiscuous compounds:	0.782

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.889	MDCK Permeability:	-4.789
Pgp-inhibitor:	0.03	Pgp-substrate:	0.004
PAMPA:	0.164 ? 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%):	0.252	30% Bioavailability (F30%):	0.383
50% Bioavailability (F50%):	0.861

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.238	MRP1:	0.216
Plasma Protein Binding (PPB):	96.232%	Volume Distribution (VD):	0.083
Fu:	3.952% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.988
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.227
BSEP inhibitor:	0.249

ADMET: Metabolism

CYP1A2-inhibitor:	0.011	CYP1A2-substrate:	0.031
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.432	CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.999	CYP2D6-substrate:	0.708
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.935
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.363 ? 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):

9.857

Half-life (T1/2):

1.221

ADMET: Toxicity

hERG Blockers:	0.297	hERG Blockers (10um):	0.633
Human Hepatotoxicity (H-HT):	0.701	Drug-induced Liver Injury (DILI):	0.092
AMES Toxicity:	0.609	Rat Oral Acute Toxicity:	0.276
Maximum Recommended Daily Dose:	0.787	Skin Sensitization:	0.955
Carcinogencity:	0.363	Eye Corrosion:	0.411
Eye Irritation:	0.998	Respiratory Toxicity:	0.396
Drug-induced Neurotoxicity:	0.525	Ototoxicity:	0.134
Hematotoxicity:	0.042	Drug-induced Nephrotoxicity:	0.114
Genotoxicity:	0.834	RPMI-8226 Immunitoxicity:	0.043
A549 Cytotoxicity:	0.324	Hek293 Cytotoxicity:	0.704
BCF:	1.784 ? 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:	3.644 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.996 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.489 ? 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
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S0040-4020(01)89039-6]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1023/A:1025674116183]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	Mengha, Yunnan Province, China	1991-Aug	PMID[11277741]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11325233]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11430002]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	Leaves, rhizomes, and roots	southeast Thailand near Chonburi	2000-Feb, 2001-Jan	PMID[12088422]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1324982]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[13465274]
NPO4703	Solanum hispidum	Species	Solanaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15217270]
NPO32936	calligonum leucocladum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217293]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1536925]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	slowly dried tubers	Bangkok, Thailand	n.a.	PMID[15679323]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	n.a.	Southeast Thailand near Chonburi, Khao Khieo, close to the Chanthathen waterfall and Sri Racha	n.a.	PMID[15679323]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679323]
NPO46	Onosma hispida	Species	Boraginaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16079517]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180822]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[16562837]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17512094]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18154272]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19376614]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19948405]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21028890]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota	n.a.	root	n.a.	PMID[21902195]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22212722]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23672042]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	seed	n.a.	PMID[24225786]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26767291]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	bark	n.a.	PMID[26767291]
NPO14359	Pentarhizidium orientale	Species	Onocleaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[28984452]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3509958]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36483735]
NPO11747	Ocimum tenuiflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39073007]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461664]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4274	Alcyonium utinomii	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5584	Aldisa sanguinea	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10525	Alnus sieboldiana	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3554	Aonidiella aurantii	Species	Diaspididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18993	Araiostegiella perdurans	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5975	Aspergillus carneus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25760	Aspergillus striatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1242	Balanops australiana	Species	Balanopaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2828	Blaps mucronata	Species	Tenebrionidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27945	Cancrinia discoidea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6231	Cortinarius odoratus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7449	Eleutherobia albiflora	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7007	Eucalyptus jenseni	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO849	Euonymus tingens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15487	Gymnopus confluens	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2250	Hylocomium splendens	Species	Hylocomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO295	Kokoona reflexa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3789	Lyonia formosa	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7760	Macrolepiota neomastoidea	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3956	Maesa ramentacea	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1390	Melolontha melolontha	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2511	Nothofagus sp.	Species	Nothofagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2993	Nototodarus sloanii	Species	Ommastrephidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11747	Ocimum tenuiflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO46	Onosma hispida	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14359	Pentarhizidium orientale	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12624	Pinus sp.	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8058	Pluchea odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1896	Proteus penneri	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1489	Pseudoplexaura flagellosa	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7606	Salacia lehmbachii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4949	Salvia yosgadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3743	Sideritis brevibracteata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5261	Sideroxylon cubense	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4703	Solanum hispidum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12104	Stemona cf. pierrei	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3408	Viguiera decurrens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31022	Nothofagus sp	Species	Nothofagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31087	Pinus sp	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10525	Alnus sieboldiana	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12104	Stemona cf. pierrei	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO46	Onosma hispida	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12104	Stemona cf. pierrei	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10525	Alnus sieboldiana	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12624	Pinus sp.	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2511	Nothofagus sp.	Species	Nothofagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14359	Pentarhizidium orientale	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO46	Onosma hispida	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	leaf and root	n.a.	n.a.	Database[Title]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO849	Euonymus tingens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11747	Ocimum tenuiflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2993	Nototodarus sloanii	Species	Ommastrephidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6231	Cortinarius odoratus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3956	Maesa ramentacea	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7606	Salacia lehmbachii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7007	Eucalyptus jenseni	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5261	Sideroxylon cubense	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2250	Hylocomium splendens	Species	Hylocomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO295	Kokoona reflexa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5975	Aspergillus carneus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18993	Araiostegiella perdurans	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15487	Gymnopus confluens	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4949	Salvia yosgadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3743	Sideritis brevibracteata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7449	Eleutherobia albiflora	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8058	Pluchea odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1390	Melolontha melolontha	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25760	Aspergillus striatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5584	Aldisa sanguinea	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1242	Balanops australiana	Species	Balanopaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3554	Aonidiella aurantii	Species	Diaspididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3789	Lyonia formosa	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7760	Macrolepiota neomastoidea	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14359	Pentarhizidium orientale	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10525	Alnus sieboldiana	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4274	Alcyonium utinomii	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3408	Viguiera decurrens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1489	Pseudoplexaura flagellosa	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27945	Cancrinia discoidea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1896	Proteus penneri	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO46	Onosma hispida	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4703	Solanum hispidum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2828	Blaps mucronata	Species	Tenebrionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	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
IC50	9
Activity	5
Inhibition	3
Efficacy	2
FC	2
MIC	7
TIME	2

Activity Type	# Activity
Individual protein	10
Cell line	5
Organism	7
Others	3
Non-molecular	5

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT13	Individual protein	Tyrosine-protein kinase LCK	Homo sapiens	IC50	=	193000.0	nM	PMID[8411012]
NPT1534	Individual protein	Transient receptor potential cation channel subfamily A member 1	Rattus norvegicus	Efficacy	<	10.0	%	PMID[26750258]
NPT1534	Individual protein	Transient receptor potential cation channel subfamily A member 1	Rattus norvegicus	IC50	=	12100.0	nM	PMID[26750258]
NPT346	Individual protein	Transient receptor potential cation channel subfamily A member 1	Homo sapiens	FC	=	-0.1	n.a.	PMID[28576617]
NPT346	Individual protein	Transient receptor potential cation channel subfamily A member 1	Homo sapiens	FC	=	0.4	n.a.	PMID[28576617]
NPT365	Individual protein	NAD(P)H dehydrogenase [quinone] 1	Mus musculus	Activity	>	20.0	uM	PMID[21215623]
NPT72	Individual protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	114.57	%	PMID[23571415]
NPT73	Individual protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	133.48	%	PMID[23571415]
NPT472	Individual protein	Vanilloid receptor	Homo sapiens	IC50	>	10000.0	nM	PMID[26750258]
NPT472	Individual protein	Vanilloid receptor	Homo sapiens	Efficacy	<	10.0	%	PMID[26750258]

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	=	10600.0	nM	PMID[15501064]
NPT116	Cell line	HL-60	Homo sapiens	Activity	=	36.95	%	PMID[19271734]
NPT1886	Cell line	J774	Mus musculus	IC50	=	16600.0	nM	PMID[29726680]
NPT1886	Cell line	J774	Mus musculus	IC50	=	32100.0	nM	PMID[29726680]
NPT1886	Cell line	J774	Mus musculus	IC50	=	38700.0	nM	PMID[29726680]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	2.04	n.a.	PMID[17316918]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	61.0	%	PMID[17316918]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	25000.0	nM	PMID[21215623]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	TIME	=	0.7167	hr	DOI[10.1007/s00044-009-9236-2]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	TIME	=	2.3	hr	DOI[10.1007/s00044-009-9236-2]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	250.0	ug.mL-1	PMID[15217293]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	125.0	ug.mL-1	PMID[15217293]
NPT1	Others	Radical scavenging activity	n.a.	Inhibition	=	29.8	%	DOI[10.1007/s00044-009-9236-2]
NPT2	Others	Unspecified	n.a.	Activity	=	1.07	uM	PMID[17316918]
NPT2	Others	Unspecified	n.a.	IC50	=	22700.0	nM	PMID[15679323]

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 NPC291789 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	32352
0.1-0.2	15808
0.2-0.3	1506
0.3-0.4	150
0.4-0.5	20
0.5-0.6	10
0.6-0.7	6
0.7-0.8	1
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
0.7143	Intermediate Similarity	NPC248573
0.7143	Intermediate Similarity	NPC161571
0.7143	Intermediate Similarity	NPC275053
0.6552	Remote Similarity	NPC176527
0.6207	Remote Similarity	NPC114392
0.6129	Remote Similarity	NPC34864
0.6129	Remote Similarity	NPC224527
0.6129	Remote Similarity	NPC105727
0.6129	Remote Similarity	NPC58427
0.5882	Remote Similarity	NPC296920
0.5882	Remote Similarity	NPC90520
0.5833	Remote Similarity	NPC114327
0.5833	Remote Similarity	NPC36357
0.5758	Remote Similarity	NPC292452
0.5405	Remote Similarity	NPC94045
0.5294	Remote Similarity	NPC61516
0.5143	Remote Similarity	NPC261343
0.5135	Remote Similarity	NPC232084
0.5135	Remote Similarity	NPC247364

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC291789 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6106
0.1-0.2	2827
0.2-0.3	209
0.3-0.4	7
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
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
0.7143	Intermediate Similarity	NPD1242	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