NPASS Compound

Natural Product: NPC213322

Natural Product ID	NPC213322
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(S)-5,7-Dihydroxy-8-Methyl-2-Phenylchroman-4-One
IUPAC Name	(2S)-5,7-dihydroxy-8-methyl-2-phenyl-2,3-dihydrochromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1269161
PubChem CID	6453244
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] Flavanones

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 34 36 0 0 0 0 0 0 0 0999 V2000 -2.0494 -2.3786 -0.2045 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3248 -0.9427 0.0548 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5743 -0.5410 0.4640 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8429 0.8101 0.7107 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8584 1.7627 0.5476 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6085 1.3710 0.1396 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5089 2.3157 -0.0575 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7777 3.5209 -0.2413 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8683 1.7622 -0.0239 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9772 0.4587 -0.7760 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2828 -0.1671 -0.4369 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2591 0.5149 0.2572 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4665 -0.0722 0.5676 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7226 -1.3697 0.1842 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7496 -2.0773 -0.5182 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5476 -1.4644 -0.8164 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1025 -0.4053 -0.5158 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3576 0.0297 -0.1008 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0668 3.1094 0.7765 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5776 -1.4599 0.6367 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9646 -2.6026 -0.1887 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6412 -3.0029 0.4726 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3903 -2.6100 -1.2480 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8213 1.1345 1.0323 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0941 1.5591 1.0505 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5394 2.5013 -0.4801 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9957 0.6388 -1.8787 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0781 1.5572 0.5762 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1840 0.5279 1.1156 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6791 -1.8415 0.4276 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9587 -3.0977 -0.8163 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8148 -2.0503 -1.3657 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3300 3.7306 0.0256 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4205 -1.2217 1.1095 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 10 17 1 0 17 18 1 0 5 19 1 0 3 20 1 0 18 2 1 0 18 6 2 0 16 11 1 0 1 21 1 0 1 22 1 0 1 23 1 0 4 24 1 0 9 25 1 0 9 26 1 0 10 27 1 6 12 28 1 0 13 29 1 0 14 30 1 0 15 31 1 0 16 32 1 0 19 33 1 0 20 34 1 0 M END

Standard InCHIKey	QSRIZZQWNHKERT-AWEZNQCLSA-N
Standard InCHI	InChI=1S/C16H14O4/c1-9-11(17)7-12(18)15-13(19)8-14(20-16(9)15)10-5-3-2-4-6-10/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1
SMILES	Cc1c(cc(c2C(=O)C[C@@H](c3ccccc3)Oc12)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	270.09	Volume:	276.329 ? Van der Waals volume.
Dense:	0.977	LogP:	3.567 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.307 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.733 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	18.0
TPSA:	66.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.835	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.862	Fsp³:	0.188
MCE-18:	54.579 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.668	Fluc inhibitor:	0.815 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.313 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.331 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.37	Promiscuous compounds:	0.039

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.929	MDCK Permeability:	-4.755
Pgp-inhibitor:	0.871	Pgp-substrate:	0.024
PAMPA:	0.075 ? 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%):	0.002	30% Bioavailability (F30%):	0.077
50% Bioavailability (F50%):	0.693

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.625	MRP1:	0.991
Plasma Protein Binding (PPB):	97.876%	Volume Distribution (VD):	0.172
Fu:	1.766% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.582
OATP1B3 inhibitor:	0.81	BCRP inhibitor:	0.506
BSEP inhibitor:	0.966

ADMET: Metabolism

CYP1A2-inhibitor:	0.569	CYP1A2-substrate:	0.994
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.997
CYP2C9-inhibitor:	0.011	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.238
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.865
HLM stability:	0.988 ? 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):

3.326

Half-life (T1/2):

1.436

ADMET: Toxicity

hERG Blockers:	0.085	hERG Blockers (10um):	0.487
Human Hepatotoxicity (H-HT):	0.818	Drug-induced Liver Injury (DILI):	0.504
AMES Toxicity:	0.676	Rat Oral Acute Toxicity:	0.769
Maximum Recommended Daily Dose:	0.687	Skin Sensitization:	0.942
Carcinogencity:	0.228	Eye Corrosion:	0.152
Eye Irritation:	0.994	Respiratory Toxicity:	0.934
Drug-induced Neurotoxicity:	0.744	Ototoxicity:	0.34
Hematotoxicity:	0.201	Drug-induced Nephrotoxicity:	0.685
Genotoxicity:	0.949	RPMI-8226 Immunitoxicity:	0.139
A549 Cytotoxicity:	0.667	Hek293 Cytotoxicity:	0.454
BCF:	1.486 ? 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:	4.154 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.472 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.823 ? 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
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF00579992]
NPO30425	Cleistocalyx operculatus	n.a.	n.a.	n.a.	n.a.	flower bud	n.a.	DOI[10.1021/np1002753]
NPO16098	Boronia pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076549]
NPO22142	Hippocratea excelsa	Species	n.a.	n.a.	root bark	n.a.	n.a.	PMID[17385912]
NPO22142	Hippocratea excelsa	Species	n.a.	n.a.	n.a.	root	n.a.	PMID[17385912]
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	stems, roots, and leaves	Da-Han Mountain, Kaohsiung, Taiwan	2004-OCT	PMID[17417907]
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17417907]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19829679]
NPO28807	Laggera pterodonta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506820]
NPO6364	Pongamiopsis pervilleana	Species	Fabaceae	Eukaryota	n.a.	Madagascar Dry Forest	n.a.	PMID[20804165]
NPO30425	Cleistocalyx operculatus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20886838]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[21087019]
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21469692]
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21469692]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22314230]
NPO22142	Hippocratea excelsa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[2292687]
NPO7890	Cleistanthus indochinensis	Species	Phyllanthaceae	Eukaryota	fruits	n.a.	n.a.	PMID[22938151]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23521110]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	leaves	n.a.	n.a.	PMID[26238320]
NPO28171	Anacyclus pyrethrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29775308]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30931559]
NPO28807	Laggera pterodonta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31664789]
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36441179]
NPO28171	Anacyclus pyrethrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37513251]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37569279]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38868673]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38999684]
NPO28171	Anacyclus pyrethrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39220961]
NPO28701	Salvia lanigera	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[8824952]
NPO27927	Alligator sinensis	Species	Alligatoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9287418]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834167]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24010	Buglossoides arvensis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28895	Pinus monticola	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8679	Streptomyces sparsogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30425	Cleistocalyx operculatus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23092	Ammodendron karelinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16098	Boronia pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27927	Alligator sinensis	Species	Alligatoridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28807	Laggera pterodonta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28414	Medicosma fareana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17288	Piliostigma thonningii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28213	Humicola grisea	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15005	Sargassum muticum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28855	Salix petiolaris	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12101	Ajuga genevensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28669	Cuscuta australis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28842	Oscillatoria raoi	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28701	Salvia lanigera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28464	Mentha sylvestris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28171	Anacyclus pyrethrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28065	Pentachondra pumila	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12835	Cyrtomium falcatum	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28145	Dendrodoris limbata	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24144	Ophiomastix mixta	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7890	Cleistanthus indochinensis	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28830	Acronychia haplophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28326	Uncaria longiflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28895	Pinus monticola	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28830	Acronychia haplophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28669	Cuscuta australis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28464	Mentha sylvestris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28326	Uncaria longiflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28669	Cuscuta australis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15319	Glochidion sphaerogynum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27988	Salvia pisidica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28895	Pinus monticola	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24010	Buglossoides arvensis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28830	Acronychia haplophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28464	Mentha sylvestris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28932	Myrrhis odorata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28830	Acronychia haplophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28807	Laggera pterodonta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28669	Cuscuta australis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24010	Buglossoides arvensis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28337	Pimpinella peregrina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28464	Mentha sylvestris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27968	Phoma linga	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28895	Pinus monticola	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28701	Salvia lanigera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28559	Julbernardia globifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12835	Cyrtomium falcatum	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28842	Oscillatoria raoi	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28623	Phlox decussata	Species	Polemoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28213	Humicola grisea	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28435	Solanum crinitum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28127	Ursinia speciosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28171	Anacyclus pyrethrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28932	Myrrhis odorata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28326	Uncaria longiflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28145	Dendrodoris limbata	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23092	Ammodendron karelinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12101	Ajuga genevensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21547	Crinum giganteum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8679	Streptomyces sparsogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28545	Scymnorhinus lichia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28578	Uperoleia inundata	Species	Myobatrachidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28280	Cetraria komarovii	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28414	Medicosma fareana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16098	Boronia pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24144	Ophiomastix mixta	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27880	Mimusops laurifolia	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7890	Cleistanthus indochinensis	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28739	Othonna macrophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28112	Amauris niavius	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27927	Alligator sinensis	Species	Alligatoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28489	Euphrasia regelii	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28196	Brachylaena perrieri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28807	Laggera pterodonta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27988	Salvia pisidica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28669	Cuscuta australis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28384	Ascotricha chartarum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28065	Pentachondra pumila	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28266	Phlomis ostrowskiana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28501	Hortonia angustifolia	Species	Monimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1118	Elymus repens	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28233	Diplotropis ferruginea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17288	Piliostigma thonningii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28855	Salix petiolaris	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15005	Sargassum muticum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6364	Pongamiopsis pervilleana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22142	Hippocratea excelsa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15319	Glochidion sphaerogynum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21904	Tarenaya spinosa	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28830	Acronychia haplophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17282	Pinguicula vulgaris	Species	Lentibulariaceae	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	2

Activity Type	# Activity
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT493	Individual protein	Neuraminidase	Influenza A virus	IC50	>	500000.0	nM	PMID[20886838]

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 NPC213322 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	24458
0.1-0.2	22035
0.2-0.3	2792
0.3-0.4	365
0.4-0.5	142
0.5-0.6	42
0.6-0.7	13
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8	Intermediate Similarity	NPC482121
0.8	Intermediate Similarity	NPC270964
0.8	Intermediate Similarity	NPC603284
0.7447	Intermediate Similarity	NPC4743
0.7234	Intermediate Similarity	NPC248372
0.6939	Remote Similarity	NPC194432
0.6939	Remote Similarity	NPC110776
0.6792	Remote Similarity	NPC76372
0.6792	Remote Similarity	NPC37496
0.66	Remote Similarity	NPC110038
0.6531	Remote Similarity	NPC243083
0.6531	Remote Similarity	NPC13768
0.6531	Remote Similarity	NPC287246
0.64	Remote Similarity	NPC177354
0.6346	Remote Similarity	NPC2416
0.6346	Remote Similarity	NPC271590
0.6275	Remote Similarity	NPC215885
0.6078	Remote Similarity	NPC312391
0.5849	Remote Similarity	NPC476153
0.5789	Remote Similarity	NPC109183
0.5769	Remote Similarity	NPC150648
0.5769	Remote Similarity	NPC37392
0.5769	Remote Similarity	NPC167624
0.5769	Remote Similarity	NPC166482
0.569	Remote Similarity	NPC175504
0.566	Remote Similarity	NPC482119
0.566	Remote Similarity	NPC296917
0.566	Remote Similarity	NPC482120
0.566	Remote Similarity	NPC170907
0.5614	Remote Similarity	NPC480991
0.5593	Remote Similarity	NPC176229
0.5577	Remote Similarity	NPC204515
0.5577	Remote Similarity	NPC482487
0.5556	Remote Similarity	NPC324134
0.5556	Remote Similarity	NPC40833
0.5517	Remote Similarity	NPC107572
0.5517	Remote Similarity	NPC32739
0.549	Remote Similarity	NPC265871
0.549	Remote Similarity	NPC205093
0.5424	Remote Similarity	NPC122894
0.5424	Remote Similarity	NPC148757
0.5424	Remote Similarity	NPC3642
0.5373	Remote Similarity	NPC605489
0.5373	Remote Similarity	NPC606578
0.5373	Remote Similarity	NPC609921
0.537	Remote Similarity	NPC255106
0.537	Remote Similarity	NPC235165
0.5283	Remote Similarity	NPC32441
0.5283	Remote Similarity	NPC79943
0.5273	Remote Similarity	NPC485881
0.5273	Remote Similarity	NPC192083
0.5254	Remote Similarity	NPC306829
0.5185	Remote Similarity	NPC20354
0.5167	Remote Similarity	NPC250214
0.5094	Remote Similarity	NPC476480
0.5094	Remote Similarity	NPC84585
0.5091	Remote Similarity	NPC274784
0.5091	Remote Similarity	NPC20709
0.5082	Remote Similarity	NPC470133
0.5082	Remote Similarity	NPC66515

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC213322 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3556
0.1-0.2	5343
0.2-0.3	239
0.3-0.4	6
0.4-0.5	3
0.5-0.6	2
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
0.6531	Remote Similarity	NPD1550	Phase 2
0.5283	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.5273	Remote Similarity	NPD2393	Clinical (unspecified phase)

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