NPASS Compound

Natural Product: NPC266689

Natural Product ID	NPC266689
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Xanthoangelol
IUPAC Name	(E)-1-[3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms	Xanthoangelol; Xanthoangerol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL494083
PubChem CID	643007
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003509] 3-prenylated chalcones

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 57 58 0 0 0 0 0 0 0 0999 V2000 -7.2369 3.2372 0.4677 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9424 2.6018 0.8271 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7904 1.3056 0.6210 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5362 0.5504 0.9408 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0082 -0.0636 -0.3087 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7374 -0.8456 -0.0456 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2298 -0.9249 1.1530 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0559 -1.5948 1.6503 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1895 -2.4003 0.8240 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5224 -3.6689 0.4173 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3114 -4.4547 -0.3321 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5290 -3.9831 -0.7041 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9479 -2.6807 -0.3234 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2570 -2.2540 -0.7597 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9531 -3.0721 -1.4572 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8441 -0.9829 -0.4744 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0751 -0.7095 -0.9426 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7361 0.5608 -0.6933 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0227 0.7706 -1.2139 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7225 1.9395 -1.0286 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1708 2.9744 -0.3055 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9111 2.7953 0.2159 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1998 1.6004 0.0245 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8329 4.1729 -0.0890 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0805 -1.9329 0.4251 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4421 -0.6438 0.8272 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7562 -4.1925 0.7741 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1050 -1.5022 -1.2061 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8367 3.4218 1.4124 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0739 4.0562 -0.2808 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9287 2.4810 0.0573 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7234 3.6541 1.3899 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6049 0.7418 0.1991 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8560 1.3043 1.3882 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8450 -0.2543 1.6343 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7460 -0.8122 -0.6617 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8228 0.6369 -1.1237 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8451 -0.3524 1.9368 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3823 -0.7749 2.1170 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2981 -2.1780 2.6213 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0133 -5.4449 -0.6312 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1976 -4.5894 -1.2944 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3496 -0.2193 0.1040 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5585 -1.4774 -1.5170 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4485 -0.0551 -1.7835 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7273 2.0621 -1.4536 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4642 3.5794 0.7779 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2110 1.5068 0.4546 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8258 4.1756 0.1209 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8638 0.1599 0.6187 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1230 -4.1220 1.7053 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4528 -0.9038 -2.1073 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3976 -2.5655 -1.3437 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0132 -1.4253 -1.2698 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1053 4.4915 1.4537 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9595 3.2601 0.7266 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5709 3.0407 2.4109 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 21 24 1 0 13 25 2 0 25 26 1 0 10 27 1 0 6 28 1 0 2 29 1 0 25 9 1 0 23 18 1 0 1 30 1 0 1 31 1 0 1 32 1 0 3 33 1 0 4 34 1 0 4 35 1 0 5 36 1 0 5 37 1 0 7 38 1 0 8 39 1 0 8 40 1 0 11 41 1 0 12 42 1 0 16 43 1 0 17 44 1 0 19 45 1 0 20 46 1 0 22 47 1 0 23 48 1 0 24 49 1 0 26 50 1 0 27 51 1 0 28 52 1 0 28 53 1 0 28 54 1 0 29 55 1 0 29 56 1 0 29 57 1 0 M END

Standard InCHIKey	LRSMBOSQWGHYCW-MDGZPELGSA-N
Standard InCHI	InChI=1S/C25H28O4/c1-17(2)5-4-6-18(3)7-13-21-24(28)16-14-22(25(21)29)23(27)15-10-19-8-11-20(26)12-9-19/h5,7-12,14-16,26,28-29H,4,6,13H2,1-3H3/b15-10+,18-7+
SMILES	CC(=CCC/C(=C/Cc1c(ccc(C(=O)/C=C/c2ccc(cc2)O)c1O)O)/C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	392.2	Volume:	432.639 ? Van der Waals volume.
Dense:	0.907	LogP:	6.031 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.235 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.548 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	16.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	2.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.295	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.719	Fsp³:	0.24
MCE-18:	15.0 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	1.0	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.477 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.598 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.659	Promiscuous compounds:	0.16

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.083	MDCK Permeability:	-4.81
Pgp-inhibitor:	0.995	Pgp-substrate:	0.0
PAMPA:	0.011 ? 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):	0.001
20% Bioavailability (F20%):	0.588	30% Bioavailability (F30%):	0.822
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.059
Plasma Protein Binding (PPB):	97.474%	Volume Distribution (VD):	0.096
Fu:	2.577% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.185
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	0.194	CYP2C19-substrate:	0.986
CYP2C9-inhibitor:	0.668	CYP2C9-substrate:	0.666
CYP2D6-inhibitor:	0.995	CYP2D6-substrate:	0.714
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.94 ? 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):

4.601

Half-life (T1/2):

1.126

ADMET: Toxicity

hERG Blockers:	0.151	hERG Blockers (10um):	0.577
Human Hepatotoxicity (H-HT):	0.745	Drug-induced Liver Injury (DILI):	0.5
AMES Toxicity:	0.152	Rat Oral Acute Toxicity:	0.222
Maximum Recommended Daily Dose:	0.552	Skin Sensitization:	0.985
Carcinogencity:	0.108	Eye Corrosion:	0.002
Eye Irritation:	0.964	Respiratory Toxicity:	0.917
Drug-induced Neurotoxicity:	0.483	Ototoxicity:	0.324
Hematotoxicity:	0.113	Drug-induced Nephrotoxicity:	0.371
Genotoxicity:	0.73	RPMI-8226 Immunitoxicity:	0.132
A549 Cytotoxicity:	0.473	Hek293 Cytotoxicity:	0.745
BCF:	1.652 ? 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:	5.256 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.771 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.343 ? 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
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	exudates	n.a.	n.a.	PMID[16441065]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[18558745]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18841906]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19102656]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21824777]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21954959]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	roots	Whitessence Srl, Viterbo, Italy	2005-OCT	PMID[21954959]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[25891102]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28075580]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	LanZhou, GanSu, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	DingXi, GanSu, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	Maturation	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	50 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	40 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	80 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	30 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	20 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	10 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	70 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	20 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	60 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	90 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	50 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	40 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	30 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	10 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	70 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	80 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	90 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	Maturation	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	60 days after pollination	PMID[33131958]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8326318]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350086]
NPO10080	Teucrium betonicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12131	Salvia calycina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14058	Papaver pavoninum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14430	Grateloupia carnosa	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15554	Eucalyptus amplifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7819.1	Epichloe festucae var. lolii	Varieties	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14309	Desmodium tortuosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12371	Artocarpus nobilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6190	Angelica archangelica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6190	Angelica archangelica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12371	Artocarpus nobilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6190	Angelica archangelica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6190	Angelica archangelica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12131	Salvia calycina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10080	Teucrium betonicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15554	Eucalyptus amplifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14309	Desmodium tortuosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14430	Grateloupia carnosa	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7819.1	Epichloe festucae var. lolii	Varieties	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6190	Angelica archangelica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12371	Artocarpus nobilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14058	Papaver pavoninum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16886	Amorpha fruticosa	Species	Fabaceae	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
Potency	36
EC50	5
AC50	4
IC50	17
Inhibition	1
Ratio	2
Activity	9
MIC	21
IC90	4
MIC50	1
MIC90	1
Ratio IC50	2
CC50	1

Activity Type	# Activity
Individual protein	37
Cell line	17
Organism	31
Unchecked	2
Protein-protein interaction	1
Others	16

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1254	Individual protein	Streptokinase A	Streptococcus pyogenes serotype M1	EC50	=	1019.0	nM	PubChem BioAssay data set
NPT2866	Individual protein	Replicative DNA helicase	Mycobacterium tuberculosis	AC50	=	3186.0	nM	PubChem BioAssay data set
NPT2867	Individual protein	Protein RecA	Mycobacterium tuberculosis	EC50	=	88400.0	nM	PubChem BioAssay data set
NPT2866	Individual protein	Replicative DNA helicase	Mycobacterium tuberculosis	AC50	=	16420.0	nM	PubChem BioAssay data set
NPT154	Individual protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	31622.8	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	32642.7	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	18356.4	nM	PubChem BioAssay data set
NPT101	Individual protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	10000.0	nM	PubChem BioAssay data set
NPT159	Individual protein	Aberrant vpr protein	Human immunodeficiency virus 1	Potency	n.a.	39810.7	nM	PubChem BioAssay data set
NPT160	Individual protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT105	Individual protein	Muscleblind-like protein 1	Homo sapiens	Potency	n.a.	125.9	nM	PubChem BioAssay data set
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	79.79	%	PMID[25891102]
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	1.97	ug.mL-1	PMID[25891102]
NPT3143	Individual protein	Solute carrier family 2, facilitated glucose transporter member 4	Rattus norvegicus	Ratio	=	1.9	n.a.	PMID[25638569]
NPT261	Individual protein	Monoamine oxidase A	Homo sapiens	IC50	>	40000.0	nM	PMID[32920430]
NPT483	Individual protein	Prelamin-A/C	Homo sapiens	Potency	=	14125.4	nM	PubChem BioAssay data set
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	35481.3	nM	PubChem BioAssay data set
NPT803	Individual protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	79432.8	nM	PubChem BioAssay data set
NPT501	Individual protein	Alpha-galactosidase A	Homo sapiens	Potency	n.a.	50118.7	nM	PubChem BioAssay data set
NPT582	Individual protein	Monoamine oxidase B	Homo sapiens	IC50	=	13200.0	nM	PMID[32920430]
NPT791	Individual protein	Cruzipain	Trypanosoma cruzi	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT94	Individual protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	3981.1	nM	PubChem BioAssay data set
NPT54	Individual protein	Nonstructural protein 1	Influenza A virus	Potency	=	11220.2	nM	PubChem BioAssay data set
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	4466.8	nM	PubChem BioAssay data set
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	19952.6	nM	PubChem BioAssay data set
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	7943.3	nM	PubChem BioAssay data set
NPT60	Individual protein	Lysosomal alpha-glucosidase	Homo sapiens	Potency	=	177.8	nM	PubChem BioAssay data set
NPT63	Individual protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	50118.7	nM	PubChem BioAssay data set
NPT478	Individual protein	Ataxin-2	Homo sapiens	Potency	n.a.	31622.8	nM	PubChem BioAssay data set
NPT5619	Individual protein	ADP-ribosylation factor GTPase-activating protein 1	Rattus norvegicus	IC50	n.a.	164708.0	nM	PubChem BioAssay data set
NPT861	Individual protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	25929.0	nM	PubChem BioAssay data set
NPT920	Individual protein	Alpha-synuclein	Homo sapiens	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT442	Individual protein	Ferritin light chain	Equus caballus	Potency	=	50118.7	nM	PubChem BioAssay data set
NPT197	Protein-protein interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	4466.8	nM	PubChem BioAssay data set
NPT532	Individual protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	39810.7	nM	PubChem BioAssay data set
NPT5	Individual protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	50118.7	nM	PubChem BioAssay data set
NPT49	Individual protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	3981.1	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[16441065]
NPT65	Cell line	HepG2	Homo sapiens	Potency	n.a.	25118.9	nM	PubChem BioAssay data set
NPT71	Cell line	HEK293	Homo sapiens	Potency	n.a.	12995.3	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	IC50	=	3980.0	nM	PMID[25590864]
NPT737	Cell line	HUVEC	Homo sapiens	IC50	>	100000.0	nM	PMID[25590864]
NPT111	Cell line	K562	Homo sapiens	Activity	=	62.3	%	PMID[25590864]
NPT171	Cell line	MRC5	Homo sapiens	IC50	=	25000.0	nM	PMID[28075580]
NPT1970	Cell line	THP-1	Homo sapiens	IC50	=	25000.0	nM	PMID[28075580]
NPT1970	Cell line	THP-1	Homo sapiens	IC50	=	23600.0	nM	PMID[31648878]
NPT171	Cell line	MRC5	Homo sapiens	IC50	=	21700.0	nM	PMID[31648878]
NPT71	Cell line	HEK293	Homo sapiens	IC50	=	21500.0	nM	PMID[31648878]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	13700.0	nM	PMID[31648878]
NPT1970	Cell line	THP-1	Homo sapiens	IC90	=	39100.0	nM	PMID[31648878]
NPT171	Cell line	MRC5	Homo sapiens	IC90	=	27600.0	nM	PMID[31648878]
NPT71	Cell line	HEK293	Homo sapiens	IC90	=	44800.0	nM	PMID[31648878]
NPT65	Cell line	HepG2	Homo sapiens	IC90	=	37400.0	nM	PMID[31648878]
NPT174	Organism	Streptococcus	Streptococcus	EC50	=	1681.0	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	8275.3	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PubChem BioAssay data set
NPT28438	Unchecked	Unchecked	n.a.	Ratio IC50	>	3.03	n.a.	PMID[32920430]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	4.0	ug.mL-1	PMID[31877539]
NPT1252	Organism	Streptococcus sp. 'group A'	Streptococcus sp. 'group A'	EC50	=	1048.0	nM	PubChem BioAssay data set
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	50000.0	nM	PMID[28075580]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	3125.0	nM	PMID[31648878]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	4.0	ug.mL-1	PMID[31877539]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25000.0	nM	PMID[28075580]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3100.0	nM	PMID[28075580]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	12500.0	nM	PMID[28075580]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	6300.0	nM	PMID[28075580]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6250.0	nM	PMID[31648878]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3125.0	nM	PMID[31648878]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	6250.0	nM	PMID[31648878]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	3125.0	nM	PMID[31648878]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100000.0	nM	PMID[31648878]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	100.0	%	PMID[31648878]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	<	20.0	CFU/ml	PMID[31648878]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC50	=	960.0	nM	PMID[31648878]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC90	=	1330.0	nM	PMID[31648878]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	4.0	ug.mL-1	PMID[31877539]
NPT2	Others	Unspecified	n.a.	IC50	=	1030.0	nM	PMID[18841906]
NPT2	Others	Unspecified	n.a.	IC50	=	1830.0	nM	PMID[18841906]
NPT2	Others	Unspecified	n.a.	IC50	>	40000.0	nM	PMID[18558745]
NPT2	Others	Unspecified	n.a.	Activity	=	20.3	%	PMID[16441065]
NPT2	Others	Unspecified	n.a.	Activity	=	0.0	%	PMID[16441065]
NPT2	Others	Unspecified	n.a.	Activity	=	64.7	%	PMID[16441065]
NPT2	Others	Unspecified	n.a.	Activity	=	87.3	%	PMID[16441065]
NPT2	Others	Unspecified	n.a.	IC50	=	273.0	molar ratio	PMID[16441065]
NPT2	Others	Unspecified	n.a.	Ratio	=	2.4	n.a.	PMID[16441065]
NPT2	Others	Unspecified	n.a.	IC50	=	980.0	nM	PMID[19102656]
NPT2	Others	Unspecified	n.a.	Potency	=	29092.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	=	9494.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	=	6421.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	25118.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	22387.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	39810.7	nM	PubChem BioAssay data set
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	12500.0	nM	PMID[28075580]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	3100.0	nM	PMID[28075580]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	MIC	>	50000.0	nM	PMID[28075580]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	MIC	>	100000.0	nM	PMID[31648878]
NPT20632	Organism	Chikungunya virus	Chikungunya virus	EC50	=	7100.0	nM	PMID[36940609]
NPT20632	Organism	Chikungunya virus	Chikungunya virus	Activity	=	8.4	%	PMID[36940609]
NPT29320	Cell line	BHK-21	Mesocricetus auratus	CC50	=	11800.0	nM	PMID[36940609]

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 NPC266689 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	16895
0.1-0.2	28620
0.2-0.3	3672
0.3-0.4	502
0.4-0.5	114
0.5-0.6	31
0.6-0.7	11
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC264112
0.8077	Intermediate Similarity	NPC72158
0.7667	Intermediate Similarity	NPC475042
0.7667	Intermediate Similarity	NPC470210
0.7458	Intermediate Similarity	NPC23126
0.7213	Intermediate Similarity	NPC21305
0.7193	Intermediate Similarity	NPC479645
0.7193	Intermediate Similarity	NPC479648
0.7049	Intermediate Similarity	NPC484873
0.6885	Remote Similarity	NPC474998
0.6875	Remote Similarity	NPC484872
0.6875	Remote Similarity	NPC477242
0.6842	Remote Similarity	NPC59319
0.6825	Remote Similarity	NPC274109
0.6786	Remote Similarity	NPC62952
0.6724	Remote Similarity	NPC100067
0.6562	Remote Similarity	NPC19622
0.6562	Remote Similarity	NPC112789
0.6552	Remote Similarity	NPC162612
0.6167	Remote Similarity	NPC213485
0.5857	Remote Similarity	NPC275903
0.5833	Remote Similarity	NPC98254
0.5738	Remote Similarity	NPC166995
0.5692	Remote Similarity	NPC483966
0.56	Remote Similarity	NPC479647
0.56	Remote Similarity	NPC479646
0.56	Remote Similarity	NPC155253
0.5538	Remote Similarity	NPC473017
0.5517	Remote Similarity	NPC91105
0.5484	Remote Similarity	NPC169250
0.5441	Remote Similarity	NPC294387
0.541	Remote Similarity	NPC190043
0.541	Remote Similarity	NPC30501
0.541	Remote Similarity	NPC65761
0.5385	Remote Similarity	NPC249606
0.5342	Remote Similarity	NPC262039
0.5325	Remote Similarity	NPC85393
0.5323	Remote Similarity	NPC472029
0.5312	Remote Similarity	NPC168105
0.5278	Remote Similarity	NPC470211
0.5278	Remote Similarity	NPC228504
0.5273	Remote Similarity	NPC19174
0.5273	Remote Similarity	NPC115159
0.5217	Remote Similarity	NPC484050
0.5217	Remote Similarity	NPC483636
0.5205	Remote Similarity	NPC237994
0.5161	Remote Similarity	NPC144343
0.5156	Remote Similarity	NPC481727
0.5156	Remote Similarity	NPC481726
0.5125	Remote Similarity	NPC271944
0.5077	Remote Similarity	NPC269694

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC266689 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4036
0.1-0.2	5008
0.2-0.3	104
0.3-0.4	2
0.4-0.5	0
0.5-0.6	0
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
		NPD

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