NPASS Compound

Natural Product: NPC86060

Natural Product ID	NPC86060
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WJSGBVFFQLYGRE-RTOZHXQVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	42632549
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

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 70 74 0 0 0 0 0 0 0 0999 V2000 6.6072 1.0874 -0.1631 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4059 0.5842 0.5711 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2050 0.3666 -0.3067 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4086 1.5758 -0.6030 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1486 1.0998 -1.3514 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3836 0.2501 -0.4041 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0422 -0.0342 -0.8152 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1683 -0.6957 -2.1391 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6813 1.3570 -0.9821 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2000 1.2337 -1.1011 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6709 0.6433 0.2039 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1106 0.8576 0.3921 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7448 1.0928 -0.9883 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2963 2.2018 1.1190 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8826 -0.2136 1.0630 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1251 -1.1718 1.8860 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6600 -1.2369 1.6925 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1841 -0.7800 0.3226 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7226 -1.7109 -0.6935 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6915 -0.7476 0.3299 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0356 -2.0913 0.5095 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3696 -1.8012 0.9293 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8175 -2.2185 1.9807 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1744 -0.9752 -0.0172 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5520 -1.8408 -1.1713 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3827 -0.4850 0.6782 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4006 -1.4474 1.0611 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3137 -2.6665 1.3150 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6081 -0.7159 1.1030 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0675 2.5661 -1.2960 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7955 2.1442 0.1544 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5029 1.0591 -1.2488 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5315 0.5321 0.1698 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1058 1.2959 1.3863 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4603 -0.1785 -1.2121 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0069 1.9702 0.3762 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4706 0.6077 -2.2789 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6312 2.0258 -1.6383 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2932 0.8520 0.5524 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8203 -0.5979 -2.6772 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4443 -1.7394 -2.1604 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8836 -0.1718 -2.8412 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4361 1.9740 -0.1224 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3621 1.7930 -1.9663 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5639 2.2967 -1.1085 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5197 0.6874 -1.9857 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1011 1.2062 1.0050 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5126 0.2973 -1.6943 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8553 1.0169 -0.7913 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5811 2.1149 -1.3453 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3409 2.5600 0.9835 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0489 2.0371 2.1909 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6192 2.9628 0.7044 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5613 -0.7533 0.3334 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6350 0.2944 1.7431 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5368 -2.2101 1.7060 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3057 -1.0222 2.9933 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3025 -2.2247 1.9817 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1854 -0.5131 2.4194 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7512 -2.1075 -0.4566 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0802 -2.6409 -0.6601 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7676 -1.3468 -1.7181 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4024 -0.1557 1.2534 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0412 -2.6796 -0.4251 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4782 -2.7342 1.2603 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3383 -2.5605 -0.7950 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0001 -1.3423 -2.0247 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7395 -2.4998 -1.5393 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1233 0.2121 1.5036 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7857 3.4549 -0.9094 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 6 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 6 24 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 4 30 1 0 29 2 1 0 26 3 1 0 24 6 1 0 20 7 1 0 18 11 1 0 1 31 1 0 1 32 1 0 1 33 1 0 2 34 1 1 3 35 1 6 4 36 1 1 5 37 1 0 5 38 1 0 6 39 1 1 8 40 1 0 8 41 1 0 8 42 1 0 9 43 1 0 9 44 1 0 10 45 1 0 10 46 1 0 11 47 1 1 13 48 1 0 13 49 1 0 13 50 1 0 14 51 1 0 14 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 16 56 1 0 16 57 1 0 17 58 1 0 17 59 1 0 19 60 1 0 19 61 1 0 19 62 1 0 20 63 1 1 21 64 1 0 21 65 1 0 25 66 1 0 25 67 1 0 25 68 1 0 26 69 1 1 30 70 1 0 M END

Standard InCHIKey	WJSGBVFFQLYGRE-RTOZHXQVSA-N
Standard InCHI	InChI=1S/C26H40O4/c1-14-20-15(27)12-18-25(5)11-8-16-23(2,3)9-7-10-24(16,4)17(25)13-19(28)26(18,6)21(20)22(29)30-14/h14-18,20-21,27H,7-13H2,1-6H3/t14-,15-,16-,17+,18-,20+,21+,24-,25+,26+/m0/s1
SMILES	C[C@H]1[C@@H]2[C@H](C[C@H]3[C@]4(C)CC[C@H]5C(C)(C)CCC[C@]5(C)[C@H]4CC(=O)[C@]3(C)[C@H]2C(=O)O1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	416.29	Volume:	445.358 ? Van der Waals volume.
Dense:	0.935	LogP:	3.311 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.331 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.465 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	27.0
TPSA:	63.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.578	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.94	Fsp³:	0.923
MCE-18:	97.92 ? 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:	0.716	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? 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:	0.155	Promiscuous compounds:	0.615

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.884	MDCK Permeability:	-4.772
Pgp-inhibitor:	0.957	Pgp-substrate:	0.0
PAMPA:	0.133 ? 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):	0.006
20% Bioavailability (F20%):	0.088	30% Bioavailability (F30%):	0.215
50% Bioavailability (F50%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.341
Plasma Protein Binding (PPB):	92.191%	Volume Distribution (VD):	0.125
Fu:	9.016% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.613
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.13
CYP2C19-inhibitor:	0.953	CYP2C19-substrate:	0.025
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.569
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.981
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.946 ? 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):

11.282

Half-life (T1/2):

1.25

ADMET: Toxicity

hERG Blockers:	0.035	hERG Blockers (10um):	0.242
Human Hepatotoxicity (H-HT):	0.601	Drug-induced Liver Injury (DILI):	0.355
AMES Toxicity:	0.336	Rat Oral Acute Toxicity:	0.227
Maximum Recommended Daily Dose:	0.592	Skin Sensitization:	0.994
Carcinogencity:	0.887	Eye Corrosion:	0.266
Eye Irritation:	0.926	Respiratory Toxicity:	0.53
Drug-induced Neurotoxicity:	0.141	Ototoxicity:	0.512
Hematotoxicity:	0.586	Drug-induced Nephrotoxicity:	0.919
Genotoxicity:	0.592	RPMI-8226 Immunitoxicity:	0.05
A549 Cytotoxicity:	0.083	Hek293 Cytotoxicity:	0.288
BCF:	1.847 ? 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:	4.464 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.933 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.507 ? 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
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	Niphates recondita	Weizhou Island, Beibuwan Bay, Guangxi,China	n.a.	PMID[24387683]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24387683]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28530828]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31265296]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32966070]
NPO12586	Tapirira guianensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9514013]
NPO9147	Frasera albomarginata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11328	Juniperus chinensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28504	Calothrix brevissima	Species	Rivulariaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3308	Calycadenia fremontii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12931	Carex pumila	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8395.1	Crepis foetida subsp. rhoeadifolia	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13038	Fomes hartigii	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12586	Tapirira guianensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8857	Hydnum repandum	Species	Hydnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10944	Mantella baroni	Species	Mantellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7116	Monachosorum henryi	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2431	Penicilliopsis zonata	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9355	Polygonatum orientale	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9977	Polygonum sieboldi	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12364	Polyides rotundus	Species	Polyideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12708	Rothia indica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6781	Senecio acanthifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5958	Senegalia modesta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5472	Spongia foliascens	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7116	Monachosorum henryi	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11328	Juniperus chinensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8857	Hydnum repandum	Species	Hydnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9147	Frasera albomarginata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9355	Polygonatum orientale	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11328	Juniperus chinensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12708	Rothia indica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13038	Fomes hartigii	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28504	Calothrix brevissima	Species	Rivulariaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8857	Hydnum repandum	Species	Hydnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9977	Polygonum sieboldi	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7116	Monachosorum henryi	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3308	Calycadenia fremontii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5958	Senegalia modesta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12364	Polyides rotundus	Species	Polyideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12931	Carex pumila	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8395.1	Crepis foetida subsp. rhoeadifolia	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10944	Mantella baroni	Species	Mantellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6781	Senecio acanthifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2431	Penicilliopsis zonata	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5472	Spongia foliascens	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12586	Tapirira guianensis	Species	Anacardiaceae	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 NPC86060 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	17004
0.1-0.2	28161
0.2-0.3	4375
0.3-0.4	285
0.4-0.5	31
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC603512
0.7143	Intermediate Similarity	NPC473299
0.5152	Remote Similarity	NPC208912

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC86060 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6465
0.1-0.2	2574
0.2-0.3	111
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