NPASS Compound

Natural Product: NPC18297

Natural Product ID	NPC18297
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RVOYIHAAPJNILN-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5316884
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 -1.5154 -3.8764 3.0026 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1338 -3.1681 1.8390 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0645 -2.2770 1.8984 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6073 -2.1062 3.1173 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6684 -1.2359 3.2191 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0786 -0.5286 2.1324 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1355 0.3516 2.1930 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7435 0.5180 3.2602 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4518 1.0083 1.0168 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7818 0.8282 -0.1696 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1159 1.5213 -1.4112 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1485 2.4214 -1.4656 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4804 3.0895 -2.6393 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7745 2.8630 -3.7895 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7342 1.9636 -3.7570 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4131 1.3030 -2.5778 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1414 3.5526 -4.9379 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7691 -0.0407 -0.1499 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4046 -0.7021 0.9162 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3481 -1.5645 0.8026 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3315 -1.7252 -0.4605 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0676 -2.6755 -1.3831 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5814 -2.8197 -2.5734 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6495 -2.0078 -2.8613 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0813 -1.0431 -1.9639 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1511 -0.2208 -2.2376 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7809 -0.3111 -3.3138 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4797 0.7107 -1.2403 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7864 0.8055 -0.0631 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1354 1.7822 0.9765 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1736 2.6578 0.8324 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5108 3.5854 1.8122 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7845 3.6394 2.9770 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7315 2.7517 3.1238 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4055 1.8410 2.1541 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1432 4.5709 3.9310 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7580 -0.0229 0.1395 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4184 -0.9047 -0.7624 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3063 -2.1508 -4.0611 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1628 -3.4615 -1.0141 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5877 -4.4403 -1.9436 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3608 -1.0398 4.4144 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3004 -4.6091 2.8163 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6422 -4.4494 3.4301 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8451 -3.1882 3.8056 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2869 -2.6626 3.9777 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2810 1.6997 1.0623 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7486 2.6560 -0.6154 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3033 3.7974 -2.6540 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1818 1.7912 -4.6717 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5999 0.5974 -2.5449 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0804 4.5601 -5.0020 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2356 -3.5794 -3.2714 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3254 1.3608 -1.4564 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7698 2.6538 -0.0594 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3312 4.2618 1.6734 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1460 2.7865 4.0487 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5894 1.1360 2.2407 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9288 5.5376 3.7936 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4454 -3.0537 -4.5008 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1518 -3.9839 -2.8036 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2691 -5.1278 -1.3662 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7457 -5.0684 -2.2825 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8577 -0.5581 5.1516 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 7 9 1 0 9 10 2 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 14 17 1 0 10 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 33 36 1 0 29 37 1 0 37 38 1 0 24 39 1 0 22 40 1 0 40 41 1 0 5 42 1 0 20 3 1 0 38 21 1 0 19 6 1 0 38 25 2 0 16 11 1 0 35 30 1 0 1 43 1 0 1 44 1 0 1 45 1 0 4 46 1 0 9 47 1 0 12 48 1 0 13 49 1 0 15 50 1 0 16 51 1 0 17 52 1 0 23 53 1 0 28 54 1 0 31 55 1 0 32 56 1 0 34 57 1 0 35 58 1 0 36 59 1 0 39 60 1 0 41 61 1 0 41 62 1 0 41 63 1 0 42 64 1 0 M END

Standard InCHIKey	RVOYIHAAPJNILN-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C32H22O10/c1-39-25-13-21(37)27-19(35)11-23(15-3-7-17(33)8-4-15)41-31(27)29(25)30-26(40-2)14-22(38)28-20(36)12-24(42-32(28)30)16-5-9-18(34)10-6-16/h3-14,33-34,37-38H,1-2H3
SMILES	COc1cc(c2c(=O)cc(c3ccc(cc3)O)oc2c1c1c(cc(c2c(=O)cc(c3ccc(cc3)O)oc12)O)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	566.12	Volume:	556.408 ? Van der Waals volume.
Dense:	1.017	LogP:	4.321 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.422 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.272 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	36.0
TPSA:	159.8 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.203	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.967	Fsp³:	0.062
MCE-18:	36.0 ? 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:	0.993	Fluc inhibitor:	0.205 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.947 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.997 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.328	Promiscuous compounds:	0.907

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.972	MDCK Permeability:	-4.771
Pgp-inhibitor:	0.034	Pgp-substrate:	0.2
PAMPA:	0.205 ? 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%):	0.041	30% Bioavailability (F30%):	0.311
50% Bioavailability (F50%):	0.945

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.606
Plasma Protein Binding (PPB):	96.755%	Volume Distribution (VD):	-0.373
Fu:	3.564% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.989
OATP1B3 inhibitor:	0.978	BCRP inhibitor:	0.701
BSEP inhibitor:	0.99

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.563
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.01
CYP2C9-inhibitor:	0.437	CYP2C9-substrate:	0.46
CYP2D6-inhibitor:	0.997	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.423
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.807 ? 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):

3.401

Half-life (T1/2):

1.709

ADMET: Toxicity

hERG Blockers:	0.085	hERG Blockers (10um):	0.498
Human Hepatotoxicity (H-HT):	0.503	Drug-induced Liver Injury (DILI):	0.993
AMES Toxicity:	0.651	Rat Oral Acute Toxicity:	0.586
Maximum Recommended Daily Dose:	0.959	Skin Sensitization:	0.507
Carcinogencity:	0.882	Eye Corrosion:	0.001
Eye Irritation:	0.972	Respiratory Toxicity:	0.859
Drug-induced Neurotoxicity:	0.017	Ototoxicity:	0.075
Hematotoxicity:	0.048	Drug-induced Nephrotoxicity:	0.021
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.115
A549 Cytotoxicity:	0.559	Hek293 Cytotoxicity:	0.963
BCF:	1.3 ? 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:	4.36 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.685 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.445 ? 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
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	leaves	Soorkesh Valley, Gollestan, Iran	n.a.	PMID[15104493]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	Leaves and branches	Soorkesh Valley, Gollestan, Iran	n.a.	PMID[15104493]
NPO28430	Biota orientalis	n.a.	n.a.	n.a.	n.a.	twig	n.a.	PMID[21793559]
NPO28430	Biota orientalis	n.a.	n.a.	n.a.	n.a.	leaf	n.a.	PMID[21793559]
NPO23434	Fissistigma latifolium	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29160716]
NPO13468.1	Cryptomeria japonica var. sinensis	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30485090]
NPO24272	Akania lucens	Species	Akaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28430	Biota orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23434	Fissistigma latifolium	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11495	Pellia epiphylla	Species	Pelliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15446	Quercus coccifera	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11328	Juniperus chinensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22216	Chimonanthus fragrans	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21146	Aloidendron sabaea	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14674	Vallesia glabra	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5174	Helenium mexicanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23575	Aspergillus restrictus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22365	Osbeckia chinensis	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28430	Biota orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO23814	Elsholtzia splendens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22216	Chimonanthus fragrans	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5174	Helenium mexicanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13513	Agathis palmerstonii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11495	Pellia epiphylla	Species	Pelliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11328	Juniperus chinensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11353	Viscaria vulgaris	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21146	Aloidendron sabaea	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20124	Xylopia discreta	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5174	Helenium mexicanum	Species	Asteraceae	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]
NPO22216	Chimonanthus fragrans	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28430	Biota orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23814	Elsholtzia splendens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28430	Biota orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22216	Chimonanthus fragrans	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23434	Fissistigma latifolium	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23814	Elsholtzia splendens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13513	Agathis palmerstonii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28430	Biota orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO11495	Pellia epiphylla	Species	Pelliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24272	Akania lucens	Species	Akaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11328	Juniperus chinensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22216	Chimonanthus fragrans	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15446	Quercus coccifera	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12500	Inga umbellifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24429	Cestrum pallidissimum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8387	Lactarius flavidulus	Species	Lactariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13599	Dryopteris abbreviata	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22365	Osbeckia chinensis	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7689	Cota triumfettii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14835	Lepraria chlorina	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11353	Viscaria vulgaris	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23575	Aspergillus restrictus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24351	Sclerotinia libertiana	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21146	Aloidendron sabaea	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24234	Agrocybe aegerita	Species	Bolbitiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25084	Dasiphora fruticosa	Species	Rosaceae	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]
NPO14674	Vallesia glabra	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23153	Eria smithii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24155	Nepeta annua	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20124	Xylopia discreta	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5174	Helenium mexicanum	Species	Asteraceae	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 NPC18297 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	29929
0.1-0.2	16244
0.2-0.3	2734
0.3-0.4	686
0.4-0.5	207
0.5-0.6	41
0.6-0.7	12
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC610914
0.8	Intermediate Similarity	NPC52611
0.7097	Intermediate Similarity	NPC601984
0.7097	Intermediate Similarity	NPC603508
0.6984	Remote Similarity	NPC290830
0.6875	Remote Similarity	NPC159707
0.6852	Remote Similarity	NPC234133
0.6769	Remote Similarity	NPC215203
0.6364	Remote Similarity	NPC301323
0.6226	Remote Similarity	NPC222713
0.6212	Remote Similarity	NPC158027
0.6182	Remote Similarity	NPC607196
0.6176	Remote Similarity	NPC601565
0.6071	Remote Similarity	NPC71334
0.6071	Remote Similarity	NPC241498
0.6071	Remote Similarity	NPC275836
0.5965	Remote Similarity	NPC198826
0.5965	Remote Similarity	NPC231018
0.5965	Remote Similarity	NPC120163
0.5909	Remote Similarity	NPC248739
0.5882	Remote Similarity	NPC194593
0.5882	Remote Similarity	NPC186227
0.5862	Remote Similarity	NPC159275
0.5862	Remote Similarity	NPC78913
0.5789	Remote Similarity	NPC47815
0.5634	Remote Similarity	NPC265624
0.5614	Remote Similarity	NPC226973
0.5593	Remote Similarity	NPC108406
0.5517	Remote Similarity	NPC306821
0.5517	Remote Similarity	NPC127447
0.5517	Remote Similarity	NPC187498
0.5517	Remote Similarity	NPC29353
0.5507	Remote Similarity	NPC71061
0.5479	Remote Similarity	NPC55443
0.5455	Remote Similarity	NPC50898
0.5424	Remote Similarity	NPC250266
0.5357	Remote Similarity	NPC296197
0.5323	Remote Similarity	NPC137062
0.5303	Remote Similarity	NPC293852
0.5286	Remote Similarity	NPC600396
0.5273	Remote Similarity	NPC216318
0.5238	Remote Similarity	NPC67322
0.5167	Remote Similarity	NPC231772
0.5167	Remote Similarity	NPC143799
0.5167	Remote Similarity	NPC146679
0.5167	Remote Similarity	NPC188203
0.5167	Remote Similarity	NPC605144
0.5161	Remote Similarity	NPC124784
0.5152	Remote Similarity	NPC288840
0.5139	Remote Similarity	NPC121649
0.5088	Remote Similarity	NPC130230
0.5085	Remote Similarity	NPC131624
0.5079	Remote Similarity	NPC183950
0.507	Remote Similarity	NPC303485
0.5068	Remote Similarity	NPC205026
0.5068	Remote Similarity	NPC111341
0.5068	Remote Similarity	NPC607327

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC18297 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5651
0.1-0.2	3416
0.2-0.3	75
0.3-0.4	6
0.4-0.5	2
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