NPASS Compound

Natural Product: NPC279013

Natural Product ID	NPC279013
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XLXOFHHXAZAIHM-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5316145
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

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 64 69 0 0 0 0 0 0 0 0999 V2000 10.7371 0.5295 -2.3938 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2792 -0.6279 -1.7277 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0144 -0.6474 -1.1457 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2128 0.4597 -1.2200 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9628 0.4909 -0.6648 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4615 -0.6332 0.0079 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2587 -1.7422 0.0850 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5391 -1.7486 -0.4939 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1263 -0.5514 0.5820 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5992 -1.6269 1.2474 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3150 -1.5635 1.8057 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 -2.5294 2.4195 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6195 -0.3939 1.6583 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1995 0.6530 0.9802 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4771 1.8188 0.8465 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1931 1.9667 1.3714 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6248 0.9096 2.0483 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3463 -0.2538 2.1813 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8049 -1.3270 2.8524 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6435 1.0053 2.5867 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7594 0.6583 1.8650 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6530 0.2014 0.5714 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8020 -0.1469 -0.1470 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0436 -0.0481 0.3983 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1368 0.4108 1.6948 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0199 0.7668 2.4413 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2560 -0.4038 -0.3269 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2565 -0.8646 -1.6106 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4174 -1.1944 -2.2748 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4304 -1.6173 -3.4501 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6314 -1.0541 -1.6179 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7984 -1.3749 -2.2557 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9790 -1.2164 -1.5554 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9587 -0.7464 -0.2507 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7756 -0.4335 0.3618 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5731 -0.5859 -0.3263 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4429 -0.2850 0.2642 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1373 -0.5869 0.4522 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7513 -1.8363 -3.5517 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4604 3.1199 1.2474 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9754 4.2623 0.5608 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4027 0.5532 0.4731 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8310 0.4187 -2.6074 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1632 0.7205 -3.2995 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6219 1.4157 -1.7130 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5707 1.3480 -1.7343 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3131 1.3578 -0.7130 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9057 -2.6247 0.5946 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1178 -2.6406 -0.4035 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1060 -2.5760 1.3931 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9137 2.6617 0.3143 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3495 -2.0508 2.3022 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6758 0.1186 0.1283 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6509 -0.4915 -1.1382 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0927 0.5140 2.1899 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1443 1.1218 3.4556 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3419 -0.9865 -2.1505 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9129 -1.4504 -2.0026 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8065 -0.0705 1.3797 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3272 0.3343 0.8362 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3424 -2.5589 -3.9249 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3574 3.9814 -0.4436 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8618 4.6280 1.1420 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2334 5.0629 0.5367 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 6 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 17 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 24 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 34 38 1 0 32 39 1 0 16 40 1 0 40 41 1 0 14 42 1 0 8 3 1 0 42 9 1 0 18 13 1 0 26 21 1 0 37 27 1 0 36 31 1 0 1 43 1 0 1 44 1 0 1 45 1 0 4 46 1 0 5 47 1 0 7 48 1 0 8 49 1 0 10 50 1 0 15 51 1 0 19 52 1 0 22 53 1 0 23 54 1 0 25 55 1 0 26 56 1 0 28 57 1 0 33 58 1 0 35 59 1 0 38 60 1 0 39 61 1 0 41 62 1 0 41 63 1 0 41 64 1 0 M END

Standard InCHIKey	XLXOFHHXAZAIHM-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C32H22O10/c1-38-19-7-3-16(4-8-19)25-14-23(36)30-27(42-25)15-28(39-2)32(31(30)37)40-20-9-5-17(6-10-20)24-13-22(35)29-21(34)11-18(33)12-26(29)41-24/h3-15,33-34,37H,1-2H3
SMILES	COc1ccc(cc1)c1cc(=O)c2c(cc(c(c2O)Oc2ccc(cc2)c2cc(=O)c3c(cc(cc3o2)O)O)OC)o1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	566.12	Volume:	556.408 ? Van der Waals volume.
Dense:	1.017	LogP:	4.267 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.239 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.33 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	36.0
TPSA:	148.8 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.214	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.855	Fsp³:	0.062
MCE-18:	35.0 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.985	Fluc inhibitor:	0.839 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.97 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.998 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.377	Promiscuous compounds:	0.912

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.06	MDCK Permeability:	-4.805
Pgp-inhibitor:	0.683	Pgp-substrate:	0.192
PAMPA:	0.208 ? 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):	0.017
20% Bioavailability (F20%):	0.384	30% Bioavailability (F30%):	0.841
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.967
Plasma Protein Binding (PPB):	98.227%	Volume Distribution (VD):	-0.305
Fu:	0.902% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.926
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.994
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.639	CYP1A2-substrate:	0.283
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.005
CYP2C9-inhibitor:	0.998	CYP2C9-substrate:	0.932
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.016	CYP3A4-substrate:	0.683
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.928 ? 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):

2.608

Half-life (T1/2):

1.36

ADMET: Toxicity

hERG Blockers:	0.221	hERG Blockers (10um):	0.585
Human Hepatotoxicity (H-HT):	0.451	Drug-induced Liver Injury (DILI):	0.994
AMES Toxicity:	0.761	Rat Oral Acute Toxicity:	0.517
Maximum Recommended Daily Dose:	0.976	Skin Sensitization:	0.29
Carcinogencity:	0.902	Eye Corrosion:	0.006
Eye Irritation:	0.989	Respiratory Toxicity:	0.872
Drug-induced Neurotoxicity:	0.022	Ototoxicity:	0.063
Hematotoxicity:	0.069	Drug-induced Nephrotoxicity:	0.023
Genotoxicity:	0.995	RPMI-8226 Immunitoxicity:	0.077
A549 Cytotoxicity:	0.553	Hek293 Cytotoxicity:	0.954
BCF:	1.375 ? 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:	4.626 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.475 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.174 ? 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
NPO30638	Cryptomeria fortunei	Species	Cupressaceae	Eukaryota	bark	n.a.	n.a.	PMID[18549276]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19481938]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28294615]
NPO13468.1	Cryptomeria japonica var. sinensis	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30485090]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31291099]
NPO1257	Distephanus angulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10922	Pentaclethra macrophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9704	Sonneratia caseolaris	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9319	Pterocaulon virgatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12205	Eucalyptus apodophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30638	Cryptomeria fortunei	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13468.1	Cryptomeria japonica var. sinensis	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30638	Cryptomeria fortunei	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22691	Mentha cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13468.1	Cryptomeria japonica var. sinensis	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6289	Ceropegia dichotoma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9704	Sonneratia caseolaris	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23384	Rhodiola semenovii	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10638	Plectranthus myrianthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3873	Crotalaria candicans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11843	Stephania zippeliana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12565	Hypericum polyanthemum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11190	Veronica polita	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10922	Pentaclethra macrophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5043	Eria japonica	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8934	Gypsophila perfoliata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9532	Vernonia cistifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1815	Breonia chinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5456	Juniperus drupacea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1257	Distephanus angulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9319	Pterocaulon virgatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21720	Talaromyces variabilis	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7822.1	Eucalyptus globulus subsp. bicostata	Subspecies	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12091	Martensia denticulata	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO526	Salvia sessei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12205	Eucalyptus apodophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11576	Glycosmis macrophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10605	Tristania conferta	Species	Myrtaceae	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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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 NPC279013 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	29180
0.1-0.2	17826
0.2-0.3	1875
0.3-0.4	737
0.4-0.5	183
0.5-0.6	42
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8939	High Similarity	NPC272064
0.7465	Intermediate Similarity	NPC600396
0.7419	Intermediate Similarity	NPC231772
0.7	Intermediate Similarity	NPC183
0.6528	Remote Similarity	NPC196179
0.6364	Remote Similarity	NPC145379
0.6324	Remote Similarity	NPC12200
0.6119	Remote Similarity	NPC62536
0.6087	Remote Similarity	NPC52005
0.6027	Remote Similarity	NPC112954
0.5974	Remote Similarity	NPC150908
0.597	Remote Similarity	NPC156222
0.597	Remote Similarity	NPC29353
0.5897	Remote Similarity	NPC303485
0.5882	Remote Similarity	NPC483773
0.5867	Remote Similarity	NPC34089
0.5823	Remote Similarity	NPC186227
0.5679	Remote Similarity	NPC601565
0.5652	Remote Similarity	NPC120464
0.5652	Remote Similarity	NPC601901
0.5634	Remote Similarity	NPC606638
0.5616	Remote Similarity	NPC605634
0.5556	Remote Similarity	NPC183950
0.55	Remote Similarity	NPC72425
0.5455	Remote Similarity	NPC50898
0.5455	Remote Similarity	NPC78540
0.5429	Remote Similarity	NPC184136
0.5429	Remote Similarity	NPC59951
0.5429	Remote Similarity	NPC57030
0.5429	Remote Similarity	NPC241838
0.5429	Remote Similarity	NPC120163
0.5375	Remote Similarity	NPC600972
0.5366	Remote Similarity	NPC143851
0.5352	Remote Similarity	NPC600900
0.5352	Remote Similarity	NPC603662
0.5309	Remote Similarity	NPC71061
0.5286	Remote Similarity	NPC239128
0.5286	Remote Similarity	NPC600177
0.5278	Remote Similarity	NPC69394
0.5244	Remote Similarity	NPC14606
0.5211	Remote Similarity	NPC234133
0.5211	Remote Similarity	NPC266597
0.5205	Remote Similarity	NPC160951
0.5205	Remote Similarity	NPC195202
0.5181	Remote Similarity	NPC121649
0.5181	Remote Similarity	NPC215203
0.5119	Remote Similarity	NPC18699
0.5072	Remote Similarity	NPC279121
0.507	Remote Similarity	NPC241498
0.507	Remote Similarity	NPC127447
0.5068	Remote Similarity	NPC255350
0.5062	Remote Similarity	NPC134796

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC279013 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5396
0.1-0.2	3672
0.2-0.3	71
0.3-0.4	9
0.4-0.5	0
0.5-0.6	2
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5072	Remote Similarity	NPD1511	Phase 2
0.5068	Remote Similarity	NPD2801	Pre-clinical

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