NPASS Compound

Natural Product: NPC27973

Natural Product ID	NPC27973
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FMQQLXJREAGPHS-OJWSHTDTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5491814
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

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 68 72 0 0 0 0 0 0 0 0999 V2000 -5.2384 -1.0941 -2.4079 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6482 -0.8112 -3.6835 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2907 0.3617 -4.3236 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5075 1.2368 -3.6317 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0771 0.9610 -2.3160 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4301 -0.1829 -1.7052 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0639 -0.5064 -0.3140 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1031 0.0894 0.4220 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8569 -0.3120 1.7433 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9627 0.2476 2.4287 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5926 -1.3272 2.3105 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3790 -1.7537 3.6103 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1346 -2.7745 4.1415 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1087 -3.3668 3.3595 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2997 -2.9264 2.0779 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5545 -1.8962 1.5065 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7458 -1.4892 0.2917 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8715 -4.4072 3.9146 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3897 -1.1417 4.3838 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3037 1.1074 -0.0724 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0287 0.8428 -0.6335 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6945 1.5503 -1.8921 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8133 1.8627 -1.9586 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5572 0.7353 -1.2674 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1280 0.6969 0.1905 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1709 1.4693 1.0034 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4135 0.8097 0.7997 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5855 1.2836 1.4095 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4387 2.3087 2.1247 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8831 0.6511 1.2395 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0688 -0.4763 0.4711 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3226 -1.0568 0.3254 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4055 -0.4939 0.9629 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2155 0.6341 1.7309 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9651 1.2009 1.8675 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3165 1.2055 2.3782 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6869 -1.0598 0.8337 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5417 -2.1918 -0.4412 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1160 1.2933 0.3554 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9172 0.8700 -1.4225 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1209 3.0951 -1.4429 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9227 0.6530 -2.9628 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1098 2.4332 -4.2108 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7360 0.5957 -5.6205 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5264 -2.0137 -1.9229 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2682 -1.5351 -4.1903 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4869 1.7106 -1.8189 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9667 -3.1078 5.1570 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0615 -3.3965 1.4796 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8689 -4.4914 3.7715 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7478 -1.7849 4.8599 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8892 -0.2540 -0.6393 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2303 2.4691 -2.0939 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0883 1.8410 -3.0257 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2359 -0.2181 -1.7513 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0459 -0.3491 0.5183 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8578 1.4191 2.0532 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2213 2.4837 0.5850 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2372 -0.9295 -0.0330 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8581 2.0886 2.4810 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5620 2.1614 2.0840 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7728 -2.0071 1.1648 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0702 -2.9547 0.0018 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1775 1.7222 -1.8593 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3464 3.6844 -1.3030 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8232 -0.2830 -2.6898 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2521 3.2679 -3.6470 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7367 1.5499 -5.9976 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 14 18 1 0 12 19 1 0 8 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 34 36 1 0 33 37 1 0 32 38 1 0 25 39 1 0 24 40 1 0 23 41 1 0 22 42 1 0 4 43 1 0 3 44 1 0 6 1 1 0 17 7 1 0 39 21 1 0 16 11 1 0 35 30 1 0 1 45 1 0 2 46 1 0 5 47 1 0 13 48 1 0 15 49 1 0 18 50 1 0 19 51 1 0 21 52 1 6 22 53 1 6 23 54 1 6 24 55 1 6 25 56 1 1 26 57 1 0 26 58 1 0 31 59 1 0 35 60 1 0 36 61 1 0 37 62 1 0 38 63 1 0 40 64 1 0 41 65 1 0 42 66 1 0 43 67 1 0 44 68 1 0 M END

Standard InCHIKey	FMQQLXJREAGPHS-OJWSHTDTSA-N
Standard InCHI	InChI=1S/C28H24O16/c29-11-6-14(32)19-17(7-11)42-25(9-1-2-12(30)13(31)3-9)26(22(19)37)44-28-24(39)23(38)21(36)18(43-28)8-41-27(40)10-4-15(33)20(35)16(34)5-10/h1-7,18,21,23-24,28-36,38-39H,8H2/t18-,21+,23+,24-,28+/m1/s1
SMILES	c1cc(c(cc1c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](COC(=O)c2cc(c(c(c2)O)O)O)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	616.11	Volume:	559.068 ? Van der Waals volume.
Dense:	1.102	LogP:	0.922 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.913 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.809 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	31.0
TPSA:	277.27 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.104	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.335	Fsp³:	0.214
MCE-18:	115.294 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.722	Fluc inhibitor:	0.299 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.89 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.658 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.18	Promiscuous compounds:	0.983

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.566	MDCK Permeability:	-4.789
Pgp-inhibitor:	0.0	Pgp-substrate:	0.037
PAMPA:	0.997 ? 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%):	0.915	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.991
Plasma Protein Binding (PPB):	84.376%	Volume Distribution (VD):	-0.023
Fu:	14.236% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.984
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.994
BSEP inhibitor:	0.885

ADMET: Metabolism

CYP1A2-inhibitor:	0.03	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.74
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
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):

3.703

Half-life (T1/2):

4.005

ADMET: Toxicity

hERG Blockers:	0.015	hERG Blockers (10um):	0.818
Human Hepatotoxicity (H-HT):	0.08	Drug-induced Liver Injury (DILI):	0.9
AMES Toxicity:	0.468	Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.747	Skin Sensitization:	1.0
Carcinogencity:	0.111	Eye Corrosion:	0.0
Eye Irritation:	0.953	Respiratory Toxicity:	0.091
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.952
Hematotoxicity:	0.001	Drug-induced Nephrotoxicity:	0.001
Genotoxicity:	0.976	RPMI-8226 Immunitoxicity:	0.007
A549 Cytotoxicity:	0.995	Hek293 Cytotoxicity:	0.585
BCF:	0.748 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.575 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.561 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.194 ? 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
NPO12926	Dendrospora tenella	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[10217713]
NPO13747	Psittacanthus cucullaris	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425137]
NPO6039	Aglaia laxiflora	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10785416]
NPO8621	Cylindrospermopsis raciborskii	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11223086]
NPO9973	Euphorbia turczaninowii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520228]
NPO8621	Cylindrospermopsis raciborskii	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14559084]
NPO7381	Ircinia spinosula	Species	Irciniidae	Eukaryota	n.a.	Bay of Naples, Italy	n.a.	PMID[7714539]
NPO5065	Cladonia fallax	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9207	Styrax ferrugineus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6039	Aglaia laxiflora	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2723	Artemisia carvifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO550	Callicarpa maingayi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3119	Cephalaria uralensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15448	Chrysothamnus parryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5541	Crotalaria aegyptiaca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8621	Cylindrospermopsis raciborskii	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7013	Dicoma capensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO762	Digitalis isabelliana	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8437	Encyothalia cliftonii	Species	Sporochnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9973	Euphorbia turczaninowii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4073	Geranium sylvaticum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26170	Haliclona mucosa	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5301	Haplophyllum ferganicum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7381	Ircinia spinosula	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2174	Polysiphonia elongata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8909	Pteris radiata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7625	Scopolia hladnikiana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8773	Sonchus ortunoi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16913	Helianthus maximiliani	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13091	Helianthus ciliaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18664	Ageratina dendroides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12926	Dendrospora tenella	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24263	Cornus kousa	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15186	Laurencia caraibica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11384	Tibouchina semidecandra	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20658	Lonicera caerulea	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13747	Psittacanthus cucullaris	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13415	Securigera coronilla	Species	Romaleidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10422	Penicillium thymicola	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14122	Clutia richardiana	Species	Peraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14772	Lesquerella auriculata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14990	Ectyoplasia ferox	Species	Raspailiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6238	Pseudo-nitzschia multiseries	Species	Bacillariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12431	Cytospora rhizophorae	Species	Valsaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12771	Eucalyptus alba	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13919	Agathis microstachya	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16913	Helianthus maximiliani	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5065	Cladonia fallax	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5065	Cladonia fallax	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13091	Helianthus ciliaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9207	Styrax ferrugineus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28816	Capnoides sempervirens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17446	Cassia kleinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16913	Helianthus maximiliani	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7310	Corchorus trilocularis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5766	Relbunium atherodes	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10049	Coleophoma empetri	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7013	Dicoma capensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5301	Haplophyllum ferganicum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4073	Geranium sylvaticum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13091	Helianthus ciliaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26170	Haliclona mucosa	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13415	Securigera coronilla	Species	Romaleidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6039	Aglaia laxiflora	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12771	Eucalyptus alba	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13625	Salacia beddomei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11384	Tibouchina semidecandra	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8909	Pteris radiata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3119	Cephalaria uralensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28041	Scaevola taccada	Species	Goodeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13518	Senecio stabianus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO762	Digitalis isabelliana	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20658	Lonicera caerulea	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5065	Cladonia fallax	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10422	Penicillium thymicola	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4245	Fagara rubescens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12431	Cytospora rhizophorae	Species	Valsaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12462	Dipodium punctatum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8437	Encyothalia cliftonii	Species	Sporochnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13919	Agathis microstachya	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7381	Ircinia spinosula	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2174	Polysiphonia elongata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12245	Lasiosiphon burchellii	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14122	Clutia richardiana	Species	Peraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO550	Callicarpa maingayi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6238	Pseudo-nitzschia multiseries	Species	Bacillariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8621	Cylindrospermopsis raciborskii	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15448	Chrysothamnus parryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17446	Cassia kleinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9973	Euphorbia turczaninowii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9097	Solanum hypomalacophyllum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5541	Crotalaria aegyptiaca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2723	Artemisia carvifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8773	Sonchus ortunoi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11782	Vateria indica	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4425	Delphinium honanense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9207	Styrax ferrugineus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19295	Bromelia plumieri	Species	Bromeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7310	Corchorus trilocularis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7625	Scopolia hladnikiana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18664	Ageratina dendroides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12926	Dendrospora tenella	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24263	Cornus kousa	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28816	Capnoides sempervirens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16913	Helianthus maximiliani	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15186	Laurencia caraibica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14772	Lesquerella auriculata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13747	Psittacanthus cucullaris	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14990	Ectyoplasia ferox	Species	Raspailiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14613	Aromadendron elegans	n.a.	n.a.	n.a.	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 NPC27973 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	18770
0.1-0.2	27357
0.2-0.3	2742
0.3-0.4	535
0.4-0.5	230
0.5-0.6	106
0.6-0.7	73
0.7-0.8	1
0.8-0.85	3
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC37668
0.9277	High Similarity	NPC270448
0.9268	High Similarity	NPC154741
0.8588	High Similarity	NPC296018
0.809	Intermediate Similarity	NPC486577
0.8046	Intermediate Similarity	NPC129264
0.8	Intermediate Similarity	NPC135831
0.7889	Intermediate Similarity	NPC97119
0.7674	Intermediate Similarity	NPC116864
0.7674	Intermediate Similarity	NPC244776
0.7312	Intermediate Similarity	NPC603079
0.7222	Intermediate Similarity	NPC67326
0.7188	Intermediate Similarity	NPC81042
0.7143	Intermediate Similarity	NPC203259
0.7143	Intermediate Similarity	NPC33054
0.7143	Intermediate Similarity	NPC176740
0.7143	Intermediate Similarity	NPC471725
0.7143	Intermediate Similarity	NPC134532
0.7143	Intermediate Similarity	NPC156869
0.7143	Intermediate Similarity	NPC602582
0.7083	Intermediate Similarity	NPC223426
0.6941	Remote Similarity	NPC127546
0.6941	Remote Similarity	NPC57625
0.6941	Remote Similarity	NPC173637
0.6941	Remote Similarity	NPC317489
0.6941	Remote Similarity	NPC223424
0.6941	Remote Similarity	NPC600591
0.6882	Remote Similarity	NPC35167
0.6882	Remote Similarity	NPC144097
0.686	Remote Similarity	NPC145038
0.686	Remote Similarity	NPC56077
0.686	Remote Similarity	NPC281131
0.686	Remote Similarity	NPC253662
0.686	Remote Similarity	NPC179950
0.686	Remote Similarity	NPC88789
0.686	Remote Similarity	NPC491374
0.6818	Remote Similarity	NPC175107
0.6809	Remote Similarity	NPC253521
0.6809	Remote Similarity	NPC113836
0.6667	Remote Similarity	NPC214621
0.6667	Remote Similarity	NPC34267
0.6667	Remote Similarity	NPC39834
0.6559	Remote Similarity	NPC471079
0.6531	Remote Similarity	NPC85751
0.6531	Remote Similarity	NPC471669
0.6531	Remote Similarity	NPC19240
0.6512	Remote Similarity	NPC67037
0.6512	Remote Similarity	NPC255615
0.6489	Remote Similarity	NPC173582
0.6489	Remote Similarity	NPC265885
0.6489	Remote Similarity	NPC181465
0.6489	Remote Similarity	NPC215710
0.6489	Remote Similarity	NPC473438
0.6489	Remote Similarity	NPC253788
0.6458	Remote Similarity	NPC470125
0.6458	Remote Similarity	NPC153755
0.6437	Remote Similarity	NPC135599
0.6437	Remote Similarity	NPC73855
0.6437	Remote Similarity	NPC113968
0.6437	Remote Similarity	NPC328940
0.6437	Remote Similarity	NPC277174
0.6437	Remote Similarity	NPC606877
0.6395	Remote Similarity	NPC276222
0.6395	Remote Similarity	NPC274618
0.6395	Remote Similarity	NPC118284
0.6395	Remote Similarity	NPC608147
0.6364	Remote Similarity	NPC19388
0.6364	Remote Similarity	NPC240431
0.6364	Remote Similarity	NPC55786
0.6316	Remote Similarity	NPC196127
0.6311	Remote Similarity	NPC292019
0.6311	Remote Similarity	NPC202908
0.6289	Remote Similarity	NPC61904
0.6286	Remote Similarity	NPC139571
0.625	Remote Similarity	NPC111929
0.625	Remote Similarity	NPC320283
0.625	Remote Similarity	NPC41121
0.6211	Remote Similarity	NPC258044
0.6211	Remote Similarity	NPC217387
0.6211	Remote Similarity	NPC609888
0.618	Remote Similarity	NPC77672
0.618	Remote Similarity	NPC133671
0.618	Remote Similarity	NPC135391
0.618	Remote Similarity	NPC78263
0.618	Remote Similarity	NPC250069
0.6162	Remote Similarity	NPC473327
0.6095	Remote Similarity	NPC217520
0.6061	Remote Similarity	NPC297503
0.6042	Remote Similarity	NPC29958
0.604	Remote Similarity	NPC476472
0.604	Remote Similarity	NPC294815
0.604	Remote Similarity	NPC16194
0.6023	Remote Similarity	NPC34531
0.6	Remote Similarity	NPC477895
0.5979	Remote Similarity	NPC471748
0.596	Remote Similarity	NPC488074
0.5934	Remote Similarity	NPC64305
0.5918	Remote Similarity	NPC605592
0.5914	Remote Similarity	NPC235260
0.5914	Remote Similarity	NPC60735
0.5914	Remote Similarity	NPC155763
0.5914	Remote Similarity	NPC219904
0.5914	Remote Similarity	NPC26230
0.5882	Remote Similarity	NPC89127
0.5876	Remote Similarity	NPC476773
0.5851	Remote Similarity	NPC120099
0.5843	Remote Similarity	NPC288084
0.5842	Remote Similarity	NPC122467
0.5806	Remote Similarity	NPC472459
0.58	Remote Similarity	NPC488073
0.58	Remote Similarity	NPC126784
0.58	Remote Similarity	NPC241423
0.5789	Remote Similarity	NPC223747
0.5755	Remote Similarity	NPC189564
0.5745	Remote Similarity	NPC182121
0.573	Remote Similarity	NPC54802
0.573	Remote Similarity	NPC197304
0.5729	Remote Similarity	NPC203050
0.5729	Remote Similarity	NPC225434
0.5714	Remote Similarity	NPC476771
0.5699	Remote Similarity	NPC52550
0.569	Remote Similarity	NPC487499
0.5673	Remote Similarity	NPC470445
0.567	Remote Similarity	NPC254855
0.567	Remote Similarity	NPC94610
0.567	Remote Similarity	NPC95866
0.5664	Remote Similarity	NPC241781
0.5652	Remote Similarity	NPC476772
0.5625	Remote Similarity	NPC156785
0.5619	Remote Similarity	NPC470446
0.56	Remote Similarity	NPC65563
0.56	Remote Similarity	NPC470949
0.5591	Remote Similarity	NPC265530
0.5579	Remote Similarity	NPC159579
0.5575	Remote Similarity	NPC480444
0.5532	Remote Similarity	NPC305811
0.5532	Remote Similarity	NPC271692
0.5521	Remote Similarity	NPC609478
0.5505	Remote Similarity	NPC303694
0.5487	Remote Similarity	NPC162394
0.5487	Remote Similarity	NPC488740
0.5487	Remote Similarity	NPC488736
0.5487	Remote Similarity	NPC488733
0.5474	Remote Similarity	NPC42773
0.5474	Remote Similarity	NPC138927
0.5474	Remote Similarity	NPC45522
0.5474	Remote Similarity	NPC325555
0.5474	Remote Similarity	NPC226304
0.5465	Remote Similarity	NPC484156
0.5463	Remote Similarity	NPC470451
0.5446	Remote Similarity	NPC155877
0.5437	Remote Similarity	NPC470443
0.5429	Remote Similarity	NPC473073
0.5426	Remote Similarity	NPC136042
0.54	Remote Similarity	NPC139320
0.5393	Remote Similarity	NPC25389
0.5392	Remote Similarity	NPC255157
0.5392	Remote Similarity	NPC259896
0.5391	Remote Similarity	NPC488737
0.5377	Remote Similarity	NPC36138
0.537	Remote Similarity	NPC121703
0.5368	Remote Similarity	NPC27640
0.5339	Remote Similarity	NPC21359
0.5339	Remote Similarity	NPC460984
0.5312	Remote Similarity	NPC599850
0.5288	Remote Similarity	NPC12013
0.5288	Remote Similarity	NPC245452
0.5288	Remote Similarity	NPC11432
0.5288	Remote Similarity	NPC477613
0.5243	Remote Similarity	NPC473571
0.5243	Remote Similarity	NPC110941
0.5243	Remote Similarity	NPC186816
0.5238	Remote Similarity	NPC104883
0.5238	Remote Similarity	NPC488679
0.5229	Remote Similarity	NPC203145
0.5204	Remote Similarity	NPC189913
0.5185	Remote Similarity	NPC470450
0.5182	Remote Similarity	NPC470416
0.5181	Remote Similarity	NPC286342
0.5152	Remote Similarity	NPC605784
0.5146	Remote Similarity	NPC473862
0.514	Remote Similarity	NPC470447
0.514	Remote Similarity	NPC477629
0.5138	Remote Similarity	NPC96605
0.5138	Remote Similarity	NPC280642
0.513	Remote Similarity	NPC480445
0.5122	Remote Similarity	NPC487502
0.5104	Remote Similarity	NPC158674
0.5102	Remote Similarity	NPC129217
0.5102	Remote Similarity	NPC488071
0.51	Remote Similarity	NPC170052
0.51	Remote Similarity	NPC476215
0.51	Remote Similarity	NPC135846
0.5098	Remote Similarity	NPC187379
0.5093	Remote Similarity	NPC292929
0.5093	Remote Similarity	NPC470449
0.5093	Remote Similarity	NPC221342
0.5093	Remote Similarity	NPC476470
0.5086	Remote Similarity	NPC474522
0.5079	Remote Similarity	NPC487500

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC27973 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4548
0.1-0.2	4540
0.2-0.3	51
0.3-0.4	7
0.4-0.5	2
0.5-0.6	1
0.6-0.7	0
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7143	Intermediate Similarity	NPD6797	Phase 2
0.5429	Remote Similarity	NPD7251	Phase 2

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