NPASS Compound

Natural Product: NPC66090

Natural Product ID	NPC66090
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MTKGYCQUEWGDQW-CRVIUCGDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	9831187
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

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 87 90 0 0 0 0 0 0 0 0999 V2000 -2.8056 -5.2599 -5.4517 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9606 -4.9926 -4.3538 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4202 -4.3327 -3.2148 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7329 -3.9144 -3.1242 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1593 -3.2629 -1.9812 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3152 -3.0085 -0.9094 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8050 -2.3646 0.3001 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9085 -0.8955 0.3658 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8262 -0.1058 0.2233 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2074 -0.0887 -0.9933 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3503 1.2747 -1.6314 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3685 2.2969 -1.2231 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1624 1.6549 -0.5370 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0375 0.3752 -1.3146 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4020 -0.1825 -1.2960 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8542 -0.5815 -0.0143 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0979 -1.1477 0.1939 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8271 -1.2976 -0.8191 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5823 -1.5674 1.5079 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7779 -2.1063 1.6254 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3763 -2.5616 2.8528 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7442 -2.4688 4.0612 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3661 -2.9291 5.2176 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6207 -3.4847 5.1793 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2829 -3.5911 3.9703 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6367 -3.1245 2.8437 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5550 -4.1519 3.9116 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2130 -4.2520 2.6651 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2648 -3.9528 6.3228 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9152 -0.5125 -0.8482 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9386 2.4838 -0.5527 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9006 3.3564 -0.5048 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7197 4.5805 -1.1181 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0926 5.1136 -1.4982 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6163 6.0800 -0.4860 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0782 5.7586 0.8833 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5762 5.8773 0.8206 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0175 5.0801 1.9875 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5968 5.5317 3.1905 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9996 5.4217 -0.3264 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5390 6.7697 1.7461 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0130 5.9732 -0.4668 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0720 5.6480 -2.7883 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3990 1.1731 -3.0184 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0215 -3.4434 -1.0486 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5562 -4.0915 -2.1598 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2430 -4.5243 -2.2826 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0012 -4.3317 -6.0344 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7670 -5.6918 -5.0867 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3167 -6.0269 -6.0640 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4200 -4.0934 -3.9381 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1754 -2.9424 -1.9179 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1665 -2.6721 1.2070 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8218 -2.8411 0.5106 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7187 -0.6080 -0.4051 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4804 -0.6475 1.3309 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7342 -0.7795 -1.6703 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3703 1.6408 -1.3222 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9182 2.7593 -2.1477 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5040 1.4260 0.5127 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2338 0.5322 -2.4048 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5387 -0.9573 -2.0749 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1091 0.6481 -1.5968 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9885 -1.4506 2.3975 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3502 -2.2073 0.6885 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7626 -2.0463 4.1718 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8690 -2.8583 6.1821 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1880 -3.2237 1.9096 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7207 -5.0303 2.0458 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2112 -3.2606 2.1649 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2766 -4.5172 2.8239 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2950 -3.9713 6.3457 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5956 2.1106 0.0907 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1550 4.4087 -2.0640 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8042 4.2564 -1.5494 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3800 7.1228 -0.7721 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3915 4.7858 1.2533 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2871 6.9481 1.0446 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1354 4.0007 1.8708 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0754 5.2892 2.0785 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5617 6.5140 3.2399 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4623 7.6097 1.2167 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3887 6.0866 -1.3685 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3078 6.2879 -2.7989 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4203 0.2383 -3.3348 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2905 -3.2801 -0.2436 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0332 -5.4804 -2.1972 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 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 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 1 0 24 29 1 0 14 30 1 0 13 31 1 0 12 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 37 40 1 0 36 41 1 0 35 42 1 0 34 43 1 0 11 44 1 0 6 45 1 0 45 46 2 0 46 47 1 0 46 3 1 0 30 10 1 0 40 33 1 0 26 21 1 0 1 48 1 0 1 49 1 0 1 50 1 0 4 51 1 0 5 52 1 0 7 53 1 0 7 54 1 0 8 55 1 0 8 56 1 0 10 57 1 6 11 58 1 1 12 59 1 6 13 60 1 1 14 61 1 6 15 62 1 0 15 63 1 0 19 64 1 0 20 65 1 0 22 66 1 0 23 67 1 0 26 68 1 0 28 69 1 0 28 70 1 0 28 71 1 0 29 72 1 0 31 73 1 0 33 74 1 6 34 75 1 6 35 76 1 6 36 77 1 1 37 78 1 1 38 79 1 0 38 80 1 0 39 81 1 0 41 82 1 0 42 83 1 0 43 84 1 0 44 85 1 0 45 86 1 0 47 87 1 0 M END

Standard InCHIKey	MTKGYCQUEWGDQW-CRVIUCGDSA-N
Standard InCHI	InChI=1S/C31H40O16/c1-41-19-7-4-16(11-18(19)34)9-10-43-30-28(40)29(47-31-27(39)26(38)24(36)21(13-32)45-31)25(37)22(46-30)14-44-23(35)8-5-15-3-6-17(33)20(12-15)42-2/h3-8,11-12,21-22,24-34,36-40H,9-10,13-14H2,1-2H3/b8-5+/t21-,22-,24-,25-,26+,27-,28-,29+,30-,31+/m1/s1
SMILES	COc1ccc(CCO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](COC(=O)/C=C/c3ccc(c(c3)OC)O)O2)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O)cc1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	668.23	Volume:	630.058 ? Van der Waals volume.
Dense:	1.061	LogP:	0.376 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.119 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.091 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	26.0
TPSA:	243.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	8.0	Rings:	4.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.09	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.674	Fsp³:	0.516
MCE-18:	99.34 ? 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:	0
Colloidal aggregators:	0.693	Fluc inhibitor:	0.662 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.155 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.594 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.072	Promiscuous compounds:	0.265

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.325	MDCK Permeability:	-5.386
Pgp-inhibitor:	0.04	Pgp-substrate:	0.102
PAMPA:	0.934 ? 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):	0.861
20% Bioavailability (F20%):	0.718	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.001
Plasma Protein Binding (PPB):	73.862%	Volume Distribution (VD):	-0.557
Fu:	25.71% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.047
BSEP inhibitor:	0.162

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.011
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.135
CYP2C9-inhibitor:	0.005	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.304
CYP3A4-inhibitor:	0.236	CYP3A4-substrate:	0.96
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.999 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

2.033

Half-life (T1/2):

3.68

ADMET: Toxicity

hERG Blockers:	0.031	hERG Blockers (10um):	0.108
Human Hepatotoxicity (H-HT):	0.399	Drug-induced Liver Injury (DILI):	0.796
AMES Toxicity:	0.973	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.012	Skin Sensitization:	1.0
Carcinogencity:	0.081	Eye Corrosion:	0.0
Eye Irritation:	0.005	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.991
Hematotoxicity:	0.297	Drug-induced Nephrotoxicity:	0.871
Genotoxicity:	0.062	RPMI-8226 Immunitoxicity:	0.272
A549 Cytotoxicity:	0.779	Hek293 Cytotoxicity:	0.714
BCF:	0.423 ? 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:	3.05 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.648 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.759 ? 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
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858748]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1367520]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974609]
NPO13010	Allium stipitatum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19093848]
NPO13010	Allium stipitatum	Species	Amaryllidaceae	Eukaryota	n.a.	bulb	n.a.	PMID[19093848]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21381678]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22118684]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	PMID[24669201]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24840014]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2488968]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	seed	n.a.	PMID[2610694]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26692349]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[31180680]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33089690]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8626236]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22203	Tapinella panuoides	Species	Tapinellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15404	Streptomyces erythrochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15898	Streptomyces noursei	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15108	Angiopteris evecta	Species	Marattiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14454	Plectranthus lanuginosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14720	Neopicrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14965	Lepidophorum repandum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15621	Lethasterias fusca	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11584	Artemisia argentea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12480	Brodiaea californica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9917	Plagiomnium cuspidatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28240	Notholaena lemmonii	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13743	Populus yunnanensis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15087	Alstonia pittieri	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16161	Stephania aculeata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12777	Laurencia pacifica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1124	Scapania aequiloba	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14720	Neopicrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9917	Plagiomnium cuspidatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14720	Neopicrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13477	Cyberlindnera jadinii	Species	Phaffomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22203	Tapinella panuoides	Species	Tapinellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13225	Spergula japonica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO255	Solanum pseudopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16161	Stephania aculeata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15087	Alstonia pittieri	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28240	Notholaena lemmonii	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13010	Allium stipitatum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14454	Plectranthus lanuginosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11584	Artemisia argentea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2667	Acacia lasiopetala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27134	Euphrasia rubra	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8556	Eucalyptus kitsoniana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10527	Cyathula tomentosa	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26381	Bombus pascuorum	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15513	Pseudocyphellaria rubella	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15806	Rhododendron campylocarpum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1777	Toddalia aculeata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9299.3	Hordeum vulgare var. distichon	Varieties	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15718	Lindera sericea	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1124	Scapania aequiloba	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15108	Angiopteris evecta	Species	Marattiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13460	Asphodeline damascena	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9917	Plagiomnium cuspidatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO14720	Neopicrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15898	Streptomyces noursei	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22101	Himantoglossum hircinum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15404	Streptomyces erythrochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26951	Gymnopus androsaceus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13743	Populus yunnanensis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11243	Exochorda giraldii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12777	Laurencia pacifica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12480	Brodiaea californica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21851	Chaetomella raphigera	Species	Chaetomellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14965	Lepidophorum repandum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29322	Rhodanthe maryonii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15621	Lethasterias fusca	Species	Asteriidae	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 NPC66090 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	16808
0.1-0.2	27298
0.2-0.3	4746
0.3-0.4	765
0.4-0.5	188
0.5-0.6	36
0.6-0.7	15
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.881	High Similarity	NPC600370
0.7529	Intermediate Similarity	NPC205195
0.6939	Remote Similarity	NPC470933
0.67	Remote Similarity	NPC476398
0.6562	Remote Similarity	NPC34927
0.6556	Remote Similarity	NPC64141
0.6471	Remote Similarity	NPC306890
0.6429	Remote Similarity	NPC259347
0.6333	Remote Similarity	NPC235294
0.6279	Remote Similarity	NPC35731
0.6237	Remote Similarity	NPC262182
0.6237	Remote Similarity	NPC476865
0.6147	Remote Similarity	NPC470927
0.6087	Remote Similarity	NPC226005
0.6082	Remote Similarity	NPC173343
0.6075	Remote Similarity	NPC476386
0.6	Remote Similarity	NPC83743
0.5976	Remote Similarity	NPC157554
0.59	Remote Similarity	NPC100998
0.5859	Remote Similarity	NPC3460
0.5851	Remote Similarity	NPC476868
0.5833	Remote Similarity	NPC188393
0.5758	Remote Similarity	NPC34587
0.5745	Remote Similarity	NPC476869
0.57	Remote Similarity	NPC252292
0.5682	Remote Similarity	NPC287597
0.5648	Remote Similarity	NPC473427
0.5575	Remote Similarity	NPC257970
0.5556	Remote Similarity	NPC300262
0.5556	Remote Similarity	NPC34293
0.549	Remote Similarity	NPC476397
0.5455	Remote Similarity	NPC288416
0.5446	Remote Similarity	NPC125823
0.5446	Remote Similarity	NPC7145
0.5446	Remote Similarity	NPC143480
0.5412	Remote Similarity	NPC307110
0.5321	Remote Similarity	NPC470934
0.5312	Remote Similarity	NPC476864
0.5288	Remote Similarity	NPC201148
0.5283	Remote Similarity	NPC476382
0.5258	Remote Similarity	NPC476866
0.5192	Remote Similarity	NPC472611
0.5149	Remote Similarity	NPC216819
0.5149	Remote Similarity	NPC80732
0.5149	Remote Similarity	NPC476383
0.5146	Remote Similarity	NPC287615
0.5096	Remote Similarity	NPC298257
0.5096	Remote Similarity	NPC175214
0.5089	Remote Similarity	NPC94871
0.5052	Remote Similarity	NPC471405
0.5052	Remote Similarity	NPC476867
0.5051	Remote Similarity	NPC90896
0.5047	Remote Similarity	NPC28651

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC66090 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4761
0.1-0.2	4253
0.2-0.3	131
0.3-0.4	3
0.4-0.5	2
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data