NPASS Compound

Natural Product: NPC94729

Natural Product ID	NPC94729
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MOJZMWJRUKIQGL-UHNOTUFWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	13751995
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 101109 0 0 0 0 0 0 0 0999 V2000 -3.1146 2.9697 0.7844 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8733 3.9060 1.7828 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8402 4.2321 2.7098 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0615 3.6027 2.6224 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2887 2.6580 1.6058 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3337 2.3378 0.6927 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6204 1.3334 -0.3497 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9443 0.6631 -0.2343 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2276 -0.0739 -1.5435 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0591 -0.9571 -1.8131 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2082 -2.0652 -2.6303 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1578 -2.9221 -2.9142 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9194 -2.6674 -2.3673 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7350 -1.5567 -1.5375 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4191 -1.3233 -0.9845 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4030 -0.8029 -1.9424 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6166 -0.4684 -3.2362 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4551 -0.0015 -4.0128 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7070 0.1087 -3.4419 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9391 -0.2262 -2.1289 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2814 -0.0914 -1.5487 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7514 -1.2777 -0.7953 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4598 -2.5471 -1.2396 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9052 -3.6513 -0.5280 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6371 -3.4849 0.6201 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9123 -2.2111 1.0389 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4836 -1.0753 0.3528 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8049 0.2058 0.8437 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8387 1.2287 -0.1395 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1330 2.5503 0.3976 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5693 3.0777 1.5390 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8861 4.3318 1.9933 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8036 5.1019 1.2861 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3906 4.6137 0.1407 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0372 3.3572 -0.2651 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3103 5.3719 -0.5778 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1676 6.3928 1.7019 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4542 1.2020 -0.7846 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5102 1.3614 0.2103 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0828 -4.5687 1.3321 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7177 -2.7508 -2.4034 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8836 -0.6778 -1.3941 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0799 -1.0234 -0.0701 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0480 -0.8023 0.9049 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0080 -1.8548 1.9421 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2760 -1.4856 3.2543 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3081 -2.4484 4.2265 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0705 -3.7903 3.9764 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2080 -4.1331 2.6755 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2466 -3.1834 1.6780 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4538 -5.4896 2.3896 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1080 -4.7605 4.9829 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3087 -0.5732 0.2886 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2356 -1.1144 1.1895 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7277 0.5760 -4.2596 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8751 -0.5896 -3.7699 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7943 -0.7270 -1.2754 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6035 0.3653 -0.4574 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8596 -3.5048 -2.6349 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4405 -2.3485 -3.1957 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9150 -0.2343 0.8278 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0511 3.9172 3.5474 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5744 5.1831 3.7127 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3582 2.7141 0.0557 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9059 4.3915 1.8380 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2807 2.2286 1.6388 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6396 1.8748 -1.3499 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8028 1.3493 -0.0652 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4558 0.6122 -2.3572 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0949 -0.7437 -1.3194 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3341 -3.7808 -3.5666 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0112 -2.3656 -0.7323 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2520 0.2573 -5.0435 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0064 -0.0025 -2.4127 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6674 -4.6598 -0.8905 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4931 -2.0317 1.9510 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5453 0.9799 -0.9594 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8594 2.4707 2.0782 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4659 4.7767 2.8812 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5153 2.9813 -1.1840 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0988 4.9293 -1.0384 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0974 6.4749 2.1189 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4486 2.0579 -1.5030 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8813 2.0962 -0.0179 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8557 -4.7297 2.3156 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6535 -3.6397 -2.8547 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3703 0.1377 1.4634 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4740 -0.4480 3.5309 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5288 -2.1951 5.2749 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4821 -3.5079 0.6566 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8567 -5.7467 1.5028 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3791 -5.7113 4.7551 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4060 0.5270 0.1781 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2862 -2.0967 0.9847 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2268 -0.1341 -4.8061 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4336 0.1855 -4.1036 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6260 -3.8484 -3.5582 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0180 -1.6100 -3.5882 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0160 -0.2971 1.2445 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0228 3.8323 3.2603 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3533 5.4876 4.3085 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 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 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 34 36 1 0 33 37 1 0 29 38 1 0 38 39 1 0 25 40 1 0 23 41 1 0 20 42 2 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 49 51 1 0 48 52 1 0 44 53 1 0 53 54 1 0 19 55 1 0 17 56 1 0 14 57 2 0 57 58 1 0 13 59 1 0 11 60 1 0 8 61 1 0 4 62 1 0 3 63 1 0 6 1 1 0 58 7 1 0 57 10 1 0 53 15 1 0 42 16 1 0 50 45 1 0 38 21 1 0 27 22 1 0 35 30 1 0 1 64 1 0 2 65 1 0 5 66 1 0 7 67 1 6 8 68 1 1 9 69 1 0 9 70 1 0 12 71 1 0 15 72 1 1 18 73 1 0 21 74 1 6 24 75 1 0 26 76 1 0 29 77 1 6 31 78 1 0 32 79 1 0 35 80 1 0 36 81 1 0 37 82 1 0 38 83 1 6 39 84 1 0 40 85 1 0 41 86 1 0 44 87 1 1 46 88 1 0 47 89 1 0 50 90 1 0 51 91 1 0 52 92 1 0 53 93 1 6 54 94 1 0 55 95 1 0 56 96 1 0 59 97 1 0 60 98 1 0 61 99 1 0 62100 1 0 63101 1 0 M END

Standard InCHIKey	MOJZMWJRUKIQGL-UHNOTUFWSA-N
Standard InCHI	InChI=1S/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37+,38+,39-,40-,41-,42-,43-/m1/s1
SMILES	c1cc(c(cc1[C@@H]1[C@@H](Cc2c(cc(c([C@H]3c4c(cc(c([C@@H]5c6c(cc(cc6O[C@H](c6ccc(c(c6)O)O)[C@@H]5O)O)O)c4O[C@H](c4ccc(c(c4)O)O)[C@@H]3O)O)O)c2O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	866.21	Volume:	820.635 ? Van der Waals volume.
Dense:	1.056	LogP:	1.119 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.549 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.201 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	51.0
TPSA:	331.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	15.0	Rings:	9.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.106	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.355	Fsp³:	0.2
MCE-18:	193.333 ? 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:	0.901	Fluc inhibitor:	0.182 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.3 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.507 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.624	Promiscuous compounds:	0.244

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.867	MDCK Permeability:	-4.734
Pgp-inhibitor:	0.0	Pgp-substrate:	0.117
PAMPA:	0.024 ? 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%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.997
Plasma Protein Binding (PPB):	87.437%	Volume Distribution (VD):	0.388
Fu:	16.231% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.017
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.992	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.0 ? 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):

7.535

Half-life (T1/2):

6.216

ADMET: Toxicity

hERG Blockers:	0.07	hERG Blockers (10um):	0.874
Human Hepatotoxicity (H-HT):	0.964	Drug-induced Liver Injury (DILI):	0.979
AMES Toxicity:	0.806	Rat Oral Acute Toxicity:	0.865
Maximum Recommended Daily Dose:	0.996	Skin Sensitization:	1.0
Carcinogencity:	0.001	Eye Corrosion:	0.0
Eye Irritation:	0.382	Respiratory Toxicity:	0.996
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.996
Hematotoxicity:	0.074	Drug-induced Nephrotoxicity:	0.329
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.117
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.999
BCF:	1.206 ? 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:	3.896 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.915 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.359 ? 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
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473412]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[15730255]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730255]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724861]
NPO26211	Knightia excelsa	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17315967]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO26507	Galenia africana	Species	Aizoaceae	Eukaryota	leaf	n.a.	n.a.	PMID[20035557]
NPO26654	Penicillium citreonigrum	Species	Aspergillaceae	Eukaryota	n.a.	atlantic-forest-soil	n.a.	PMID[20450206]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21302965]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26566007]
NPO26451	Ophiocoma scolopendrina	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27684202]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7288445]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26507	Galenia africana	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26374	Alangium premnifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26023	Angelica tarokoensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25896	Bragantia wallichii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26607	Colobocentrotus atratus	Species	Echinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25792	Delphinium andersoni	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26184	Diphasia angolensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25739	Erysimum odoratum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25972	Eupolyphaga sinensis	Species	Corydiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26349	Frullania tamarisci	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26161	Globba malaccensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26584	Gnidia lamprantha	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26624	Ilex amara	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26211	Knightia excelsa	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25995	Laurencia distichophylla	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26699	Leonurus glaucescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26950	Maba buxifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26561	Micromeria pineolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7447	Nemalion vermiculare	Species	Liagoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26806	Nidula candida	Species	Nidulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26451	Ophiocoma scolopendrina	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26654	Penicillium citreonigrum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2898	Quercus sessiliflora	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26406	Saussurea carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26319	Solanum acaule	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26287	Spodoptera eridania	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25949	Streptomyces griseovariabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26052	Swertia delavayi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26900	Vallota purpurea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25923	Vismia jefensis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26699	Leonurus glaucescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26349	Frullania tamarisci	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25972	Eupolyphaga sinensis	Species	Corydiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25972	Eupolyphaga sinensis	Species	Corydiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2898	Quercus sessiliflora	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26607	Colobocentrotus atratus	Species	Echinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26287	Spodoptera eridania	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26699	Leonurus glaucescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26561	Micromeria pineolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26349	Frullania tamarisci	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26900	Vallota purpurea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26654	Penicillium citreonigrum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26184	Diphasia angolensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26584	Gnidia lamprantha	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25896	Bragantia wallichii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26161	Globba malaccensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26451	Ophiocoma scolopendrina	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25923	Vismia jefensis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26211	Knightia excelsa	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26406	Saussurea carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26624	Ilex amara	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26023	Angelica tarokoensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26950	Maba buxifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26319	Solanum acaule	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26806	Nidula candida	Species	Nidulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7447	Nemalion vermiculare	Species	Liagoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25949	Streptomyces griseovariabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26052	Swertia delavayi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25739	Erysimum odoratum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25792	Delphinium andersoni	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26374	Alangium premnifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25995	Laurencia distichophylla	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26507	Galenia africana	Species	Aizoaceae	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 NPC94729 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	21450
0.1-0.2	24893
0.2-0.3	3150
0.3-0.4	203
0.4-0.5	62
0.5-0.6	28
0.6-0.7	32
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC246202
1.0	High Similarity	NPC224161
1.0	High Similarity	NPC46335
1.0	High Similarity	NPC279406
1.0	High Similarity	NPC486519
0.9821	High Similarity	NPC58190
0.9821	High Similarity	NPC108811
0.9821	High Similarity	NPC170103
0.9821	High Similarity	NPC236202
0.9821	High Similarity	NPC262911
0.9821	High Similarity	NPC202742
0.8594	High Similarity	NPC278548
0.8281	Intermediate Similarity	NPC226809
0.8167	Intermediate Similarity	NPC96576
0.8095	Intermediate Similarity	NPC313116
0.8095	Intermediate Similarity	NPC603340
0.7846	Intermediate Similarity	NPC70409
0.7846	Intermediate Similarity	NPC204770
0.7846	Intermediate Similarity	NPC600551
0.7846	Intermediate Similarity	NPC601980
0.7846	Intermediate Similarity	NPC602065
0.7846	Intermediate Similarity	NPC611024
0.7612	Intermediate Similarity	NPC600630
0.7612	Intermediate Similarity	NPC607896
0.7612	Intermediate Similarity	NPC611369
0.7568	Intermediate Similarity	NPC212614
0.7568	Intermediate Similarity	NPC205613
0.7534	Intermediate Similarity	NPC86630
0.75	Intermediate Similarity	NPC294558
0.75	Intermediate Similarity	NPC18185
0.75	Intermediate Similarity	NPC263940
0.75	Intermediate Similarity	NPC147743
0.75	Intermediate Similarity	NPC4809
0.75	Intermediate Similarity	NPC73517
0.7463	Intermediate Similarity	NPC211561
0.7432	Intermediate Similarity	NPC106601
0.7432	Intermediate Similarity	NPC151474
0.7167	Intermediate Similarity	NPC178054
0.7077	Intermediate Similarity	NPC601999
0.7051	Intermediate Similarity	NPC159526
0.6957	Remote Similarity	NPC601997
0.6957	Remote Similarity	NPC609211
0.6957	Remote Similarity	NPC610665
0.6897	Remote Similarity	NPC261619
0.6897	Remote Similarity	NPC61477
0.6897	Remote Similarity	NPC78770
0.6897	Remote Similarity	NPC219876
0.6897	Remote Similarity	NPC126029
0.6897	Remote Similarity	NPC15658
0.6761	Remote Similarity	NPC302549
0.6618	Remote Similarity	NPC184245
0.6618	Remote Similarity	NPC187801
0.6618	Remote Similarity	NPC610920
0.6575	Remote Similarity	NPC20050
0.6538	Remote Similarity	NPC78074
0.6486	Remote Similarity	NPC306267
0.64	Remote Similarity	NPC135021
0.6389	Remote Similarity	NPC272552
0.6389	Remote Similarity	NPC226108
0.6389	Remote Similarity	NPC322899
0.6364	Remote Similarity	NPC9309
0.6329	Remote Similarity	NPC478340
0.6301	Remote Similarity	NPC46283
0.6301	Remote Similarity	NPC469944
0.6267	Remote Similarity	NPC478616
0.6267	Remote Similarity	NPC478339
0.625	Remote Similarity	NPC478337
0.625	Remote Similarity	NPC478338
0.6216	Remote Similarity	NPC44192
0.6087	Remote Similarity	NPC277331
0.6087	Remote Similarity	NPC100482
0.6071	Remote Similarity	NPC478617
0.5867	Remote Similarity	NPC65333
0.5867	Remote Similarity	NPC134911
0.5857	Remote Similarity	NPC82917
0.5738	Remote Similarity	NPC207179
0.5738	Remote Similarity	NPC167571
0.5738	Remote Similarity	NPC278552
0.5696	Remote Similarity	NPC471404
0.5694	Remote Similarity	NPC165483
0.5663	Remote Similarity	NPC479793
0.5616	Remote Similarity	NPC28440
0.5541	Remote Similarity	NPC155564
0.5529	Remote Similarity	NPC479794
0.5484	Remote Similarity	NPC268266
0.5484	Remote Similarity	NPC42760
0.5484	Remote Similarity	NPC220825
0.5484	Remote Similarity	NPC268342
0.5373	Remote Similarity	NPC171932
0.5342	Remote Similarity	NPC20757
0.5342	Remote Similarity	NPC227516
0.5323	Remote Similarity	NPC601844
0.5147	Remote Similarity	NPC16435
0.5111	Remote Similarity	NPC185231
0.5075	Remote Similarity	NPC36835
0.5075	Remote Similarity	NPC246162
0.5075	Remote Similarity	NPC9743
0.5075	Remote Similarity	NPC260491
0.5075	Remote Similarity	NPC61506
0.5075	Remote Similarity	NPC240476

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC94729 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4313
0.1-0.2	4765
0.2-0.3	63
0.3-0.4	7
0.4-0.5	0
0.5-0.6	0
0.6-0.7	2
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
0.6897	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1613	Phase 4

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