NPASS Compound

Natural Product: NPC186727

Natural Product ID	NPC186727
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FYBMGZSDYDNBFX-GXPPAHCZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5491657
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 73 77 0 0 0 0 0 0 0 0999 V2000 2.5508 2.6199 1.9761 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1787 1.9975 0.7644 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6497 2.3612 0.6354 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2646 1.3255 -0.2804 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1645 0.8958 -1.2645 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1113 0.1453 -0.5130 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0879 0.6037 0.8196 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8081 0.3471 -1.0119 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1916 -0.8213 -1.3337 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9766 -0.8923 -2.8651 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6654 -2.3497 -3.1021 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5127 -2.8018 -2.2819 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7395 -4.3060 -2.4725 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7118 -4.5384 -3.8291 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5166 -2.4430 -0.9748 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1517 -1.0809 -0.7674 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3521 -0.7693 0.6025 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5936 -0.6510 1.1539 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1331 -1.8733 1.6171 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4809 -2.9188 1.5074 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3708 -1.9197 2.1872 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8879 -3.1133 2.6335 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1336 -3.1771 3.2088 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8745 -2.0249 3.3394 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3543 -0.8344 2.8924 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0929 -0.7642 2.3089 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5775 0.3362 1.8801 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3604 0.4414 1.3101 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9530 1.7539 0.8937 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6822 2.0851 0.5498 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3431 3.3705 0.0982 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3144 4.3290 -0.0011 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5946 4.0170 0.3409 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9046 2.7456 0.7816 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5549 5.0109 0.2299 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9578 5.6097 -0.4546 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1271 -2.0315 3.9073 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1290 -4.2483 2.4917 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5442 -2.6511 -4.4364 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0484 -0.4472 -3.5780 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7719 0.1455 -2.2752 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6780 0.1873 0.3847 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8098 3.6181 0.0186 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7816 1.9220 2.3764 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3659 2.8242 2.7045 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0406 3.5815 1.7770 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6401 2.3226 -0.1365 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0977 2.3429 1.6523 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1004 1.7887 -0.8309 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7943 1.8264 -1.7393 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3476 -0.9562 -0.4992 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9022 -1.6844 -1.1324 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0228 -0.3320 -3.0589 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5614 -2.9113 -2.7059 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4157 -2.3269 -2.7603 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0505 -4.9096 -1.8791 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7823 -4.5656 -2.1276 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1060 -5.2732 -4.0952 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9296 -0.5545 -1.3349 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5451 -4.1061 3.5602 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9324 0.0597 2.9956 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1410 1.4030 0.6330 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6569 3.6417 -0.1786 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9444 2.5679 1.0366 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8652 5.5388 1.0136 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4905 6.0854 -1.1589 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4424 -2.7466 4.5686 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3244 -4.4496 3.0558 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2519 -3.2646 -4.7435 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0951 0.5363 -3.5062 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7778 0.2081 -2.2244 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4509 0.1684 1.3326 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7038 3.9744 0.3137 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 33 35 1 0 32 36 1 0 24 37 1 0 22 38 1 0 11 39 1 0 10 40 1 0 5 41 1 0 4 42 1 0 3 43 1 0 7 2 1 0 16 9 1 0 28 18 2 0 34 29 1 0 26 21 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 6 3 48 1 1 4 49 1 6 5 50 1 6 6 51 1 1 9 52 1 1 10 53 1 1 11 54 1 1 12 55 1 6 13 56 1 0 13 57 1 0 14 58 1 0 16 59 1 6 23 60 1 0 25 61 1 0 30 62 1 0 31 63 1 0 34 64 1 0 35 65 1 0 36 66 1 0 37 67 1 0 38 68 1 0 39 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 43 73 1 0 M END

Standard InCHIKey	FYBMGZSDYDNBFX-GXPPAHCZSA-N
Standard InCHI	InChI=1S/C27H30O16/c1-8-17(33)20(36)22(38)26(39-8)43-25-21(37)18(34)15(7-28)41-27(25)42-24-19(35)16-13(32)5-10(29)6-14(16)40-23(24)9-2-3-11(30)12(31)4-9/h2-6,8,15,17-18,20-22,25-34,36-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,22+,25+,26-,27-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1Oc1c(=O)c2c(cc(cc2oc1c1ccc(c(c1)O)O)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.15	Volume:	552.318 ? Van der Waals volume.
Dense:	1.105	LogP:	0.91 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.298 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.614 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	269.43 ? 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:	0.14	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.777	Fsp³:	0.444
MCE-18:	122.949 ? 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:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.621	Fluc inhibitor:	0.279 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.84 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.6 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.3	Promiscuous compounds:	0.61

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.552	MDCK Permeability:	-5.041
Pgp-inhibitor:	0.0	Pgp-substrate:	0.427
PAMPA:	0.998 ? 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):	0.987
20% Bioavailability (F20%):	0.936	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.042
Plasma Protein Binding (PPB):	80.756%	Volume Distribution (VD):	-0.198
Fu:	16.643% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.698
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.01	CYP2D6-substrate:	0.804
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.005
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.593 ? 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):

1.938

Half-life (T1/2):

4.728

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.141
Human Hepatotoxicity (H-HT):	0.51	Drug-induced Liver Injury (DILI):	0.955
AMES Toxicity:	0.852	Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.033	Skin Sensitization:	1.0
Carcinogencity:	0.075	Eye Corrosion:	0.0
Eye Irritation:	0.675	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.971
Hematotoxicity:	0.044	Drug-induced Nephrotoxicity:	0.276
Genotoxicity:	0.98	RPMI-8226 Immunitoxicity:	0.069
A549 Cytotoxicity:	0.759	Hek293 Cytotoxicity:	0.551
BCF:	0.445 ? 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:	3.038 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.576 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.703 ? 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
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1002/ejlt.201100207]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1007/s11746-010-1670-2]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.foodcont.2016.09.002]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.jfca.2010.08.006]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2010.06.003]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2010.12.007]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2016.02.010]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2018.06.017]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.12691/jfnr-2-5-9]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.5219/332]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[10336650]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217296]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679315]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252923]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499319]
NPO13478	Scorzonera pseudodivaricata	Species	Asteraceae	Eukaryota	n.a.	Mongolian	n.a.	PMID[17542634]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[17624889]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	sand-covered bottom at -10 to -15 m at Hurghada, on the Egyptian Red Sea coast	2003-JUN	PMID[18298079]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18611049]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18768384]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18942825]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19476340]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[19628108]
NPO12855	Alkanna cappadocica	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20405844]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21912858]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[22111577]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	flower	n.a.	PMID[22166201]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[22538527]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23790907]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[24811150]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24948953]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25564559]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[28274428]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29154541]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[30236698]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30384263]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	Guangzhou, China		PMID[30563201]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[30583361]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[30599958]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[31159190]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[31861466]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36613240]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37631012]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38354824]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39199155]
NPO12855	Alkanna cappadocica	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13030	Artemisia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1834	Atalantia racemosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21830	Buddleja cordata	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12196	Buphane fischeri	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5930	Crambe tatarica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12700	Diospyros eriantha	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9313	Fritillaria ningguoensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO252	Hoffmannia strigillosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24390.1	Juniperus rigida var. conferta	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11848	Lemaireocereus griseus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9934	Mycobacterium leprae	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13671	Ononis vaginalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14578	Prorocentrum micans	Species	Prorocentraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8928	Pteris semipinnata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13585	Rapanea lancifolia	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13478	Scorzonera pseudodivaricata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10783	Syncarpia hillii	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6360	Xenoacremonium recifei	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1982	Tilia miqueliana	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO1982	Tilia miqueliana	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9313	Fritillaria ningguoensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1982	Tilia miqueliana	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24390.1	Juniperus rigida var. conferta	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1834	Atalantia racemosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9313	Fritillaria ningguoensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8928	Pteris semipinnata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9934	Mycobacterium leprae	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10783	Syncarpia hillii	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13585	Rapanea lancifolia	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13030	Artemisia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21830	Buddleja cordata	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12855	Alkanna cappadocica	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12700	Diospyros eriantha	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6360	Xenoacremonium recifei	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11848	Lemaireocereus griseus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24390.1	Juniperus rigida var. conferta	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9313	Fritillaria ningguoensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13478	Scorzonera pseudodivaricata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO252	Hoffmannia strigillosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14578	Prorocentrum micans	Species	Prorocentraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5930	Crambe tatarica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12196	Buphane fischeri	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1834	Atalantia racemosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1982	Tilia miqueliana	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13671	Ononis vaginalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2675	Cordyline neocaledonica	Species	Asparagaceae	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 NPC186727 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	21809
0.1-0.2	23645
0.2-0.3	3511
0.3-0.4	437
0.4-0.5	202
0.5-0.6	60
0.6-0.7	96
0.7-0.8	0
0.8-0.85	7
0.85-0.9	1
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC155877
0.9221	High Similarity	NPC254855
0.9221	High Similarity	NPC94610
0.9114	High Similarity	NPC163242
0.9114	High Similarity	NPC272068
0.8974	High Similarity	NPC95866
0.8375	Intermediate Similarity	NPC170052
0.8375	Intermediate Similarity	NPC135846
0.8372	Intermediate Similarity	NPC220173
0.8214	Intermediate Similarity	NPC255157
0.8214	Intermediate Similarity	NPC259896
0.8148	Intermediate Similarity	NPC476215
0.814	Intermediate Similarity	NPC122467
0.7778	Intermediate Similarity	NPC602448
0.7471	Intermediate Similarity	NPC304741
0.7471	Intermediate Similarity	NPC605592
0.7416	Intermediate Similarity	NPC12013
0.7416	Intermediate Similarity	NPC11432
0.7416	Intermediate Similarity	NPC477613
0.7386	Intermediate Similarity	NPC470444
0.7368	Intermediate Similarity	NPC303694
0.7363	Intermediate Similarity	NPC473071
0.7363	Intermediate Similarity	NPC89127
0.7303	Intermediate Similarity	NPC240306
0.7284	Intermediate Similarity	NPC127546
0.7284	Intermediate Similarity	NPC57625
0.7284	Intermediate Similarity	NPC173637
0.7284	Intermediate Similarity	NPC317489
0.7284	Intermediate Similarity	NPC223424
0.7284	Intermediate Similarity	NPC600591
0.7195	Intermediate Similarity	NPC145038
0.7195	Intermediate Similarity	NPC56077
0.7195	Intermediate Similarity	NPC281131
0.7195	Intermediate Similarity	NPC253662
0.7195	Intermediate Similarity	NPC179950
0.7195	Intermediate Similarity	NPC88789
0.7195	Intermediate Similarity	NPC491374
0.7159	Intermediate Similarity	NPC470405
0.7159	Intermediate Similarity	NPC471748
0.7143	Intermediate Similarity	NPC32641
0.7143	Intermediate Similarity	NPC256188
0.7059	Intermediate Similarity	NPC224530
0.7045	Intermediate Similarity	NPC29958
0.703	Intermediate Similarity	NPC480444
0.6957	Remote Similarity	NPC35119
0.6923	Remote Similarity	NPC253521
0.6923	Remote Similarity	NPC113836
0.6915	Remote Similarity	NPC221342
0.6915	Remote Similarity	NPC476470
0.6889	Remote Similarity	NPC203259
0.6889	Remote Similarity	NPC33054
0.6889	Remote Similarity	NPC176740
0.6889	Remote Similarity	NPC471725
0.6889	Remote Similarity	NPC134532
0.6889	Remote Similarity	NPC602582
0.6875	Remote Similarity	NPC89052
0.6829	Remote Similarity	NPC67037
0.6829	Remote Similarity	NPC255615
0.6809	Remote Similarity	NPC76831
0.6737	Remote Similarity	NPC292929
0.6735	Remote Similarity	NPC219043
0.6703	Remote Similarity	NPC156869
0.6698	Remote Similarity	NPC21359
0.6698	Remote Similarity	NPC460984
0.6667	Remote Similarity	NPC480441
0.663	Remote Similarity	NPC115674
0.6602	Remote Similarity	NPC488740
0.6602	Remote Similarity	NPC488736
0.6602	Remote Similarity	NPC488733
0.6598	Remote Similarity	NPC14187
0.6571	Remote Similarity	NPC192539
0.6566	Remote Similarity	NPC292019
0.6566	Remote Similarity	NPC202908
0.6548	Remote Similarity	NPC111929
0.6548	Remote Similarity	NPC320283
0.6548	Remote Similarity	NPC41121
0.6505	Remote Similarity	NPC480445
0.6484	Remote Similarity	NPC139320
0.6476	Remote Similarity	NPC488737
0.6471	Remote Similarity	NPC77672
0.6471	Remote Similarity	NPC133671
0.6471	Remote Similarity	NPC135391
0.6471	Remote Similarity	NPC78263
0.6471	Remote Similarity	NPC250069
0.6452	Remote Similarity	NPC35167
0.6442	Remote Similarity	NPC162394
0.6437	Remote Similarity	NPC216496
0.6404	Remote Similarity	NPC136761
0.64	Remote Similarity	NPC48984
0.6383	Remote Similarity	NPC61904
0.6374	Remote Similarity	NPC473682
0.6364	Remote Similarity	NPC203145
0.6353	Remote Similarity	NPC135599
0.6353	Remote Similarity	NPC73855
0.6353	Remote Similarity	NPC113968
0.6353	Remote Similarity	NPC328940
0.6353	Remote Similarity	NPC277174
0.6353	Remote Similarity	NPC606877
0.633	Remote Similarity	NPC487499
0.63	Remote Similarity	NPC488075
0.6279	Remote Similarity	NPC19388
0.6279	Remote Similarity	NPC240431
0.6279	Remote Similarity	NPC55786
0.6238	Remote Similarity	NPC173837
0.6237	Remote Similarity	NPC173582
0.6237	Remote Similarity	NPC265885
0.6237	Remote Similarity	NPC181465
0.6237	Remote Similarity	NPC215710
0.6237	Remote Similarity	NPC473438
0.6237	Remote Similarity	NPC253788
0.6207	Remote Similarity	NPC64305
0.6195	Remote Similarity	NPC249560
0.618	Remote Similarity	NPC60735
0.618	Remote Similarity	NPC175107
0.618	Remote Similarity	NPC219904
0.618	Remote Similarity	NPC26230
0.6176	Remote Similarity	NPC25523
0.617	Remote Similarity	NPC65003
0.6147	Remote Similarity	NPC25946
0.6146	Remote Similarity	NPC480471
0.6146	Remote Similarity	NPC488076
0.6139	Remote Similarity	NPC473072
0.6118	Remote Similarity	NPC288084
0.6111	Remote Similarity	NPC120099
0.6106	Remote Similarity	NPC487502
0.6095	Remote Similarity	NPC488734
0.6095	Remote Similarity	NPC488735
0.6095	Remote Similarity	NPC488739
0.6095	Remote Similarity	NPC488732
0.6095	Remote Similarity	NPC488738
0.6087	Remote Similarity	NPC116864
0.6087	Remote Similarity	NPC244776
0.6067	Remote Similarity	NPC472459
0.6064	Remote Similarity	NPC67326
0.6064	Remote Similarity	NPC39834
0.6044	Remote Similarity	NPC223747
0.6044	Remote Similarity	NPC605784
0.6022	Remote Similarity	NPC8856
0.602	Remote Similarity	NPC142142
0.6018	Remote Similarity	NPC30011
0.598	Remote Similarity	NPC189564
0.5978	Remote Similarity	NPC203050
0.5978	Remote Similarity	NPC225434
0.596	Remote Similarity	NPC471669
0.5955	Remote Similarity	NPC52550
0.5934	Remote Similarity	NPC609478
0.593	Remote Similarity	NPC276222
0.593	Remote Similarity	NPC274618
0.593	Remote Similarity	NPC34531
0.593	Remote Similarity	NPC118284
0.593	Remote Similarity	NPC608147
0.5918	Remote Similarity	NPC473327
0.5905	Remote Similarity	NPC470718
0.5897	Remote Similarity	NPC487500
0.5865	Remote Similarity	NPC470712
0.5847	Remote Similarity	NPC487501
0.5843	Remote Similarity	NPC265530
0.5841	Remote Similarity	NPC473554
0.58	Remote Similarity	NPC476472
0.58	Remote Similarity	NPC294815
0.58	Remote Similarity	NPC16194
0.5789	Remote Similarity	NPC258044
0.5789	Remote Similarity	NPC217387
0.5778	Remote Similarity	NPC305811
0.5761	Remote Similarity	NPC259957
0.5714	Remote Similarity	NPC42773
0.5714	Remote Similarity	NPC64425
0.5714	Remote Similarity	NPC45522
0.5714	Remote Similarity	NPC325555
0.5714	Remote Similarity	NPC226304
0.5714	Remote Similarity	NPC599850
0.57	Remote Similarity	NPC97119
0.5688	Remote Similarity	NPC156785
0.5667	Remote Similarity	NPC136042
0.5652	Remote Similarity	NPC235260
0.5652	Remote Similarity	NPC155763
0.5644	Remote Similarity	NPC195257
0.5625	Remote Similarity	NPC480442
0.5604	Remote Similarity	NPC271692
0.5603	Remote Similarity	NPC72554
0.56	Remote Similarity	NPC482026
0.5596	Remote Similarity	NPC470713
0.5591	Remote Similarity	NPC484158
0.5586	Remote Similarity	NPC241781
0.5565	Remote Similarity	NPC275977
0.5565	Remote Similarity	NPC231787
0.5556	Remote Similarity	NPC126784
0.5556	Remote Similarity	NPC241423
0.5532	Remote Similarity	NPC116458
0.5532	Remote Similarity	NPC246943
0.55	Remote Similarity	NPC245452
0.5484	Remote Similarity	NPC48093
0.5464	Remote Similarity	NPC480466
0.5464	Remote Similarity	NPC471079
0.5455	Remote Similarity	NPC144097
0.5446	Remote Similarity	NPC209550
0.5446	Remote Similarity	NPC37668
0.5444	Remote Similarity	NPC476771
0.5443	Remote Similarity	NPC286342
0.5435	Remote Similarity	NPC84362

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC186727 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5900
0.1-0.2	3168
0.2-0.3	72
0.3-0.4	4
0.4-0.5	4
0.5-0.6	1
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6889	Remote Similarity	NPD6797	Phase 2
0.534	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