NPASS Compound

Natural Product: NPC310956

Natural Product ID	NPC310956
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RQBNSDSKUAGBOI-JOTVTJJCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101967086
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 85 89 0 0 0 0 0 0 0 0999 V2000 5.7793 0.4893 1.7149 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0882 1.0087 0.4395 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0023 0.7029 -0.6910 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7479 0.4062 0.4015 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8088 -1.1157 0.3601 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4261 -1.5650 0.8557 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3719 -1.1220 -0.1709 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6122 -1.8978 -1.4037 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4343 0.3509 -0.2591 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2923 0.9589 -1.0587 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9715 0.6329 -0.2346 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1172 -0.8163 -0.3395 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3177 -1.4611 0.2016 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8895 -2.9049 0.3350 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3802 -2.9340 0.0239 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0181 -1.5119 0.3692 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0527 -1.4183 1.8655 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5623 -1.2933 -0.6229 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4720 -1.8429 -2.0056 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7514 -1.9438 0.0528 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8669 -0.9540 -0.1644 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1965 0.2250 -0.7724 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6301 1.4757 -0.0621 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1077 1.6963 -0.1009 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1763 1.5161 1.3789 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9921 2.5613 -0.7008 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8420 0.0637 -0.7118 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7756 0.9453 -0.5963 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1680 0.8269 -2.0202 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6644 2.4543 -0.3121 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0317 3.1099 -0.3018 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0007 2.5025 0.6353 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2650 3.0222 0.3577 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0128 0.3893 2.5355 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4905 1.2600 2.0806 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3292 -0.4364 1.5268 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0557 0.8745 -0.3135 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9912 -0.3569 -1.0028 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9170 1.4125 -1.5537 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2744 0.6271 1.4110 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0603 -1.5177 -0.6110 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5309 -1.4769 1.0987 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3835 -2.6325 1.0591 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2506 -0.9249 1.7512 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5326 -1.7143 -1.9469 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6818 -2.9855 -1.0920 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7746 -1.7754 -2.1456 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2350 0.7234 0.7970 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2296 0.4827 -2.0590 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3433 2.0407 -1.0779 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8254 1.2420 -0.5537 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7151 0.9395 0.8108 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0117 -1.1095 -1.4245 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5538 -0.9982 1.2031 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4442 -3.5579 -0.3917 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0972 -3.3307 1.3304 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1432 -3.6925 0.6007 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3478 -3.1126 -1.0891 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1014 -0.4147 2.2713 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0114 -1.8481 2.2223 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7107 -2.1576 2.2538 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3896 -1.4713 -2.5526 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6001 -2.9654 -2.0218 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6225 -1.5117 -2.6004 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5002 -2.0743 1.1294 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9685 -2.9455 -0.3506 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6019 -1.4534 -0.8530 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3687 -0.7860 0.7869 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5390 0.3178 -1.8254 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5908 1.4709 0.8925 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6240 1.1188 -0.9085 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3067 2.7769 -0.2726 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2679 0.5325 1.8839 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7730 2.2294 1.9690 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1053 1.7986 1.4426 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6540 3.1261 -1.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0016 0.1466 -2.2395 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4805 1.8103 -2.4896 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2344 0.5697 -2.6047 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0760 2.6673 0.5748 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1759 2.8923 -1.2347 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4633 3.1476 -1.3057 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8538 4.1634 0.0108 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7869 2.7695 1.7031 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6374 3.5528 1.0989 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 6 7 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 1 13 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 23 26 1 0 22 27 1 0 9 28 1 0 28 29 1 6 28 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 2 1 0 28 4 1 0 16 7 1 0 27 18 1 0 16 12 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 1 5 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 8 45 1 0 8 46 1 0 8 47 1 0 9 48 1 1 10 49 1 0 10 50 1 0 11 51 1 0 11 52 1 0 12 53 1 6 13 54 1 1 14 55 1 0 14 56 1 0 15 57 1 0 15 58 1 0 17 59 1 0 17 60 1 0 17 61 1 0 19 62 1 0 19 63 1 0 19 64 1 0 20 65 1 0 20 66 1 0 21 67 1 0 21 68 1 0 22 69 1 6 24 70 1 0 24 71 1 0 24 72 1 0 25 73 1 0 25 74 1 0 25 75 1 0 26 76 1 0 29 77 1 0 29 78 1 0 29 79 1 0 30 80 1 0 30 81 1 0 31 82 1 0 31 83 1 0 32 84 1 1 33 85 1 0 M END

Standard InCHIKey	RQBNSDSKUAGBOI-JOTVTJJCSA-N
Standard InCHI	InChI=1S/C30H52O3/c1-25(2)21-12-17-29(7)22(27(21,5)15-13-23(25)31)10-9-19-20(11-16-28(19,29)6)30(8)18-14-24(33-30)26(3,4)32/h19-24,31-32H,9-18H2,1-8H3/t19-,20+,21+,22-,23+,24+,27+,28-,29-,30-/m1/s1
SMILES	CC1(C)[C@@H]2CC[C@]3(C)[C@H](CC[C@@H]4[C@H](CC[C@@]34C)[C@@]3(C)CC[C@@H](C(C)(C)O)O3)[C@@]2(C)CC[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	460.39	Volume:	511.024 ? Van der Waals volume.
Dense:	0.901	LogP:	4.702 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.298 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.525 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	25.0
TPSA:	49.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.48	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.776	Fsp³:	1.0
MCE-18:	105.3 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.89	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.494	Promiscuous compounds:	0.307

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.138	MDCK Permeability:	-5.018
Pgp-inhibitor:	0.823	Pgp-substrate:	0.166
PAMPA:	0.257 ? 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%):	0.19	30% Bioavailability (F30%):	0.024
50% Bioavailability (F50%):	0.904

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.955	MRP1:	0.972
Plasma Protein Binding (PPB):	97.914%	Volume Distribution (VD):	-0.179
Fu:	2.877% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.372
BSEP inhibitor:	0.987

ADMET: Metabolism

CYP1A2-inhibitor:	0.997	CYP1A2-substrate:	0.006
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.601	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.817	CYP2D6-substrate:	0.427
CYP3A4-inhibitor:	0.289	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.822
HLM stability:	0.56 ? 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):

12.0

Half-life (T1/2):

0.441

ADMET: Toxicity

hERG Blockers:	0.159	hERG Blockers (10um):	0.407
Human Hepatotoxicity (H-HT):	0.621	Drug-induced Liver Injury (DILI):	0.158
AMES Toxicity:	0.53	Rat Oral Acute Toxicity:	0.485
Maximum Recommended Daily Dose:	0.633	Skin Sensitization:	0.984
Carcinogencity:	0.881	Eye Corrosion:	0.108
Eye Irritation:	0.718	Respiratory Toxicity:	0.777
Drug-induced Neurotoxicity:	0.16	Ototoxicity:	0.494
Hematotoxicity:	0.356	Drug-induced Nephrotoxicity:	0.547
Genotoxicity:	0.826	RPMI-8226 Immunitoxicity:	0.06
A549 Cytotoxicity:	0.295	Hek293 Cytotoxicity:	0.517
BCF:	2.196 ? 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:	3.839 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.963 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.51 ? 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
NPO3125	Scaphechinus mirabilis	Species	Scutellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180820]
NPO18521	Capparis flavicans	Species	Capparaceae	Eukaryota	aerial parts	Khon Kaen Province, Thailand	2006-Aug	PMID[19943620]
NPO27620	Pteris cretica	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28006909]
NPO17392	Ipomoea hederacea	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3125	Scaphechinus mirabilis	Species	Scutellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16834	Baccharis sarothroides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21188	Merremia quinquefolia	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1757	Aconitum liljestrandii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17969	Unona lawii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20531	Helichrysum splendidum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27620	Pteris cretica	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18712	Malus sieboldii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17392	Ipomoea hederacea	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20990	Garcinia ovalifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27620	Pteris cretica	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16834	Baccharis sarothroides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17392	Ipomoea hederacea	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20990	Garcinia ovalifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21188	Merremia quinquefolia	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1757	Aconitum liljestrandii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17392	Ipomoea hederacea	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20302	Betonica grandiflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20990	Garcinia ovalifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19951	Parmelia amphixanthoides	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21188	Merremia quinquefolia	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20531	Helichrysum splendidum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18521	Capparis flavicans	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16834	Baccharis sarothroides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15360	Stephania hispidula	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19591	Dendrocalamus strictus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1604	Micranthes stellaris	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3125	Scaphechinus mirabilis	Species	Scutellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18307	Peltigera venosa	Species	Peltigeraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17604	Lasioderma serricorne	Species	Anobiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1757	Aconitum liljestrandii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3113	Xyris semifuscata	Species	Xyridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17720	Andropogon laniger	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18712	Malus sieboldii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27620	Pteris cretica	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17392	Ipomoea hederacea	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12652	Xylosalsola richteri	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16655	Rabdosia flexicaulis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21261	Funtumia africana	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13976	Sonchus gummifer	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19129	Oxytropis pseudoglandulosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13598	Pedicularis plicata	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15625	Umbilicaria spodochroa	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17969	Unona lawii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC310956 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	22921
0.1-0.2	23368
0.2-0.3	3046
0.3-0.4	375
0.4-0.5	93
0.5-0.6	33
0.6-0.7	13
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC91387
1.0	High Similarity	NPC231680
1.0	High Similarity	NPC270306
0.8333	Intermediate Similarity	NPC133596
0.8333	Intermediate Similarity	NPC11907
0.7455	Intermediate Similarity	NPC64081
0.6897	Remote Similarity	NPC245029
0.6897	Remote Similarity	NPC31302
0.6786	Remote Similarity	NPC58631
0.678	Remote Similarity	NPC190940
0.678	Remote Similarity	NPC292458
0.678	Remote Similarity	NPC217559
0.678	Remote Similarity	NPC268578
0.6613	Remote Similarity	NPC111582
0.625	Remote Similarity	NPC103782
0.6032	Remote Similarity	NPC250687
0.6032	Remote Similarity	NPC48824
0.6032	Remote Similarity	NPC148740
0.6032	Remote Similarity	NPC102156
0.5938	Remote Similarity	NPC80700
0.5873	Remote Similarity	NPC474574
0.5846	Remote Similarity	NPC254572
0.5846	Remote Similarity	NPC229407
0.5846	Remote Similarity	NPC269267
0.5833	Remote Similarity	NPC201725
0.5797	Remote Similarity	NPC114378
0.5758	Remote Similarity	NPC311642
0.5758	Remote Similarity	NPC164289
0.5758	Remote Similarity	NPC100366
0.5758	Remote Similarity	NPC471747
0.5758	Remote Similarity	NPC242771
0.5636	Remote Similarity	NPC232112
0.5517	Remote Similarity	NPC480925
0.5517	Remote Similarity	NPC48079
0.5484	Remote Similarity	NPC81074
0.5484	Remote Similarity	NPC477282
0.5246	Remote Similarity	NPC245869
0.5231	Remote Similarity	NPC477577
0.5161	Remote Similarity	NPC285761
0.5161	Remote Similarity	NPC34930
0.5152	Remote Similarity	NPC477285
0.5139	Remote Similarity	NPC479791
0.5085	Remote Similarity	NPC142712
0.5082	Remote Similarity	NPC97534
0.5082	Remote Similarity	NPC195155
0.5079	Remote Similarity	NPC602784
0.5077	Remote Similarity	NPC49599
0.5077	Remote Similarity	NPC49627
0.5077	Remote Similarity	NPC477508
0.5077	Remote Similarity	NPC603388
0.5075	Remote Similarity	NPC131665
0.5075	Remote Similarity	NPC255387

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC310956 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7293
0.1-0.2	1796
0.2-0.3	59
0.3-0.4	1
0.4-0.5	1
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