NPASS Compound

Natural Product: NPC247219

Natural Product ID	NPC247219
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GRVQPMQMSRMJNS-KGHUUUROSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2227747
PubChem CID	45276503
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

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 91 0 0 0 0 0 0 0 0999 V2000 -3.5007 -4.5316 1.2642 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9759 -3.7376 0.0905 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1531 -2.3110 0.3788 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9605 -1.3173 -0.4333 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1706 0.0714 0.0351 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0092 1.1162 -0.7506 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2133 2.4628 -0.2322 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3737 3.1099 -0.5343 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6051 4.3943 -0.0486 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6339 4.9791 0.7353 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8414 6.3461 1.2739 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4440 4.3269 1.0483 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2704 3.0872 0.5530 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9945 2.3691 0.8150 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3885 2.5862 1.8529 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5343 1.4877 -0.1020 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3658 0.7326 0.0156 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6363 -0.6929 -0.4539 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5719 -1.3443 -1.0088 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2180 -2.6517 -1.7353 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2727 -2.8326 -1.8212 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8356 -3.8478 -1.1911 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0106 -4.8160 -0.4076 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3300 -3.9965 -1.2194 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6376 -5.3092 -1.6403 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2468 -0.5496 -1.9008 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8198 0.5674 -1.2658 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5016 1.3414 -2.3380 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5158 2.1080 -2.0142 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9021 2.1312 -0.5606 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2158 2.8299 -0.4983 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8880 0.6881 -0.1482 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4010 0.4063 1.2299 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2096 -1.1041 1.4592 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3877 -1.8239 0.8669 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6046 -1.6880 1.7745 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4555 -0.3401 2.4509 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8944 0.6267 1.3919 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5716 0.2583 -0.1945 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6483 1.4311 -0.8535 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8013 5.0413 -0.3681 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4819 -4.2352 1.5570 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5560 -5.6109 1.1219 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1154 -4.2381 2.1924 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0818 -4.1413 -0.1113 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4958 -2.1047 1.4353 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -1.3790 -1.4387 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4620 0.1346 1.0598 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7762 1.0883 -1.7912 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0829 2.5806 -1.1781 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6843 6.8658 0.8111 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9067 6.9164 1.0931 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9705 6.2645 2.3884 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6809 4.8211 1.6821 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0676 0.7029 1.0818 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0547 -1.2399 0.4084 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3618 -0.5795 -1.3020 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2800 -1.6824 -0.1943 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7202 -3.5249 -1.2898 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5610 -2.6178 -2.8012 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7816 -2.1126 -2.4356 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4501 -4.3634 0.4219 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5928 -5.6781 -0.0624 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2094 -5.2606 -1.0793 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7194 -3.2798 -1.9652 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9832 -5.8476 -0.8824 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1494 1.2637 -3.3896 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0467 2.6971 -2.7737 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1873 2.7358 0.0423 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0829 2.2740 -0.8430 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1265 3.6893 -1.2491 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3354 3.3744 0.4638 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5155 0.1384 -0.9156 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8128 0.9850 1.9682 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3080 -1.3959 0.9256 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1544 -1.3394 2.5420 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1571 -2.9145 0.6927 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6812 -1.4367 -0.1253 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5512 -1.6949 1.1937 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6333 -2.5286 2.4735 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7640 -0.3605 3.3111 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4190 0.0742 2.7867 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1119 1.6231 1.8025 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4021 0.3664 0.4615 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9007 2.3939 -0.4278 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1058 1.6558 -1.8215 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9043 5.3165 -1.3549 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 22 24 1 0 24 25 1 0 19 26 1 0 27 26 1 6 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 30 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 32 39 1 0 27 40 1 0 9 41 1 0 24 2 1 0 39 27 1 0 13 7 1 0 40 17 1 0 38 33 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 6 3 46 1 0 4 47 1 0 5 48 1 0 6 49 1 0 8 50 1 0 11 51 1 0 11 52 1 0 11 53 1 0 12 54 1 0 17 55 1 1 18 56 1 0 18 57 1 0 19 58 1 1 20 59 1 0 20 60 1 0 21 61 1 0 23 62 1 0 23 63 1 0 23 64 1 0 24 65 1 6 25 66 1 0 28 67 1 0 29 68 1 0 30 69 1 1 31 70 1 0 31 71 1 0 31 72 1 0 32 73 1 6 33 74 1 0 34 75 1 0 34 76 1 0 35 77 1 0 35 78 1 0 36 79 1 0 36 80 1 0 37 81 1 0 37 82 1 0 38 83 1 0 38 84 1 0 40 85 1 0 40 86 1 0 41 87 1 0 M END

Standard InCHIKey	GRVQPMQMSRMJNS-KGHUUUROSA-N
Standard InCHI	InChI=1S/C35H46O6/c1-22-10-8-9-13-27-19-31(36)25(4)18-30(27)34(38)39-29-20-28(15-14-23(2)32(22)37)40-35(21-29)17-16-24(3)33(41-35)26-11-6-5-7-12-26/h8-10,13-14,16-19,22,24,26,28-29,32-33,36-37H,5-7,11-12,15,20-21H2,1-4H3/b10-8+,13-9+,23-14+/t22-,24-,28+,29-,32-,33-,35+/m0/s1
SMILES	C[C@H]1/C=C/C=C/c2cc(c(C)cc2C(=O)O[C@H]2C[C@@H](C/C=C(C)/[C@H]1O)O[C@@]1(C=C[C@H](C)[C@@H](C3CCCCC3)O1)C2)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	562.33	Volume:	602.783 ? Van der Waals volume.
Dense:	0.933	LogP:	4.346 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.758 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.507 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	38.0
TPSA:	85.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.278	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.613	Fsp³:	0.571
MCE-18:	142.036 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.992	Fluc inhibitor:	0.64 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.396 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.486 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.159	Promiscuous compounds:	0.193

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.401	MDCK Permeability:	-4.937
Pgp-inhibitor:	0.364	Pgp-substrate:	0.075
PAMPA:	0.119 ? 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%):	0.121	30% Bioavailability (F30%):	0.581
50% Bioavailability (F50%):	0.932

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013	MRP1:	0.99
Plasma Protein Binding (PPB):	98.24%	Volume Distribution (VD):	0.174
Fu:	1.758% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.944	BCRP inhibitor:	0.008
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.906
CYP2C19-inhibitor:	0.011	CYP2C19-substrate:	0.014
CYP2C9-inhibitor:	0.006	CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.003	CYP2D6-substrate:	0.869
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.998 ? 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):

4.954

Half-life (T1/2):

0.63

ADMET: Toxicity

hERG Blockers:	0.211	hERG Blockers (10um):	0.428
Human Hepatotoxicity (H-HT):	0.83	Drug-induced Liver Injury (DILI):	0.996
AMES Toxicity:	0.743	Rat Oral Acute Toxicity:	0.196
Maximum Recommended Daily Dose:	0.899	Skin Sensitization:	1.0
Carcinogencity:	0.221	Eye Corrosion:	0.008
Eye Irritation:	0.781	Respiratory Toxicity:	0.357
Drug-induced Neurotoxicity:	0.818	Ototoxicity:	0.435
Hematotoxicity:	0.061	Drug-induced Nephrotoxicity:	0.779
Genotoxicity:	0.649	RPMI-8226 Immunitoxicity:	0.235
A549 Cytotoxicity:	0.889	Hek293 Cytotoxicity:	0.915
BCF:	1.055 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.044 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.353 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.885 ? 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
NPO2303	Sinularia scabra	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502336]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1367520]
NPO2303	Sinularia scabra	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620256]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974609]
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]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	roots and rhizomes	n.a.	n.a.	PMID[25835537]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26692349]
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]
NPO15499	Boletus radicans	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO350	Piper cenocladum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3282	Baeckea brevifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5000	Cordyceps brongniartii	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14185	Helianthopsis utcubambensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16671	Lysimachia vulgaris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12115	Odontaster validus	Species	Odontasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14993	Poecillastra laminaris	Species	Vulcanellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13532	Prorocentrum hoffmannianum	Species	Prorocentraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13362	Scabiosa bipinnata	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2303	Sinularia scabra	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14368	Stephania sinica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28362	Tacca paxiana	Species	Taccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11138	Veronicastrum sibiricum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10754	Zanthoxylum clava-herculis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO350	Piper cenocladum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14368	Stephania sinica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11138	Veronicastrum sibiricum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO350	Piper cenocladum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11138	Veronicastrum sibiricum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14368	Stephania sinica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11138	Veronicastrum sibiricum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14993	Poecillastra laminaris	Species	Vulcanellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2303	Sinularia scabra	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3282	Baeckea brevifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13532	Prorocentrum hoffmannianum	Species	Prorocentraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14185	Helianthopsis utcubambensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11138	Veronicastrum sibiricum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15499	Boletus radicans	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5000	Cordyceps brongniartii	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10754	Zanthoxylum clava-herculis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12115	Odontaster validus	Species	Odontasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14368	Stephania sinica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13362	Scabiosa bipinnata	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16671	Lysimachia vulgaris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO350	Piper cenocladum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28362	Tacca paxiana	Species	Taccaceae	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

Activity Type	# Activity
Activity	10
mortality	5

Activity Type	# Activity
Organism	15

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
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	Activity	=	0.0	%	PMID[20000422]
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	Activity	=	12.1	%	PMID[20000422]
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	Activity	=	19.8	%	PMID[20000422]
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	Activity	=	37.6	%	PMID[20000422]
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	Activity	=	56.7	%	PMID[20000422]
NPT530	Organism	Caenorhabditis elegans	Caenorhabditis elegans	Activity	=	13.5	%	PMID[20000422]
NPT530	Organism	Caenorhabditis elegans	Caenorhabditis elegans	Activity	=	49.2	%	PMID[20000422]
NPT530	Organism	Caenorhabditis elegans	Caenorhabditis elegans	Activity	=	81.4	%	PMID[20000422]
NPT530	Organism	Caenorhabditis elegans	Caenorhabditis elegans	Activity	=	100.0	%	PMID[20000422]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	mortality	=	45.2	%	PMID[20000422]
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	mortality	=	77.1	%	PMID[20000422]
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	mortality	=	92.5	%	PMID[20000422]
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	mortality	=	100.0	%	PMID[20000422]

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 NPC247219 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	11604
0.1-0.2	37645
0.2-0.3	607
0.3-0.4	2
0.4-0.5	0
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	Natural Product ID
		NPC

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC247219 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5309
0.1-0.2	3825
0.2-0.3	16
0.3-0.4	0
0.4-0.5	0
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