NPASS Compound

Natural Product: NPC328714

Natural Product ID	NPC328714
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2R,3R)-2-[(3S,8S,9S,10R,13S,14S,17S)-3-Hydroxy-10,13-Dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-Dodecahydro-1H-Cyclopenta[A]Phenanthren-17-Yl]-6-Methylheptane-2,3-Diol
IUPAC Name	(2R,3R)-2-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylheptane-2,3-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL560194
PubChem CID	6453841
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0001104] Trihydroxy bile acids, alcohols 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 76 79 0 0 0 0 0 0 0 0999 V2000 -7.1650 2.0007 -0.6242 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5618 1.0096 0.3535 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8156 1.3698 1.7783 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0399 0.9918 0.0543 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4583 0.0263 1.0079 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9744 -0.1842 0.9856 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4709 -0.6707 -0.3266 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2244 -1.8974 -0.7190 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0005 -0.7111 -0.4886 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7100 -1.1711 -1.9032 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7073 -1.6836 -1.8957 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0810 -1.8792 -0.4739 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0874 -1.4122 0.4017 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5322 -0.4287 1.4089 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3134 0.6704 0.7736 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3666 0.1729 -0.2191 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4038 -1.3085 -0.0794 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4480 -1.9566 -0.9662 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6247 -1.0872 -1.1118 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7505 0.1573 -0.7228 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6602 0.8879 -0.0492 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0894 1.0543 1.4000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6087 1.0017 1.5244 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3058 1.6489 0.3568 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0431 0.9219 -0.9280 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6713 1.6306 0.6447 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4845 2.2886 -0.6184 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5213 -2.5665 1.2182 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8481 0.3279 -1.2432 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7434 -1.0236 2.0722 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2537 1.4957 -1.6111 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4330 2.8404 -0.7000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1456 2.3285 -0.2557 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9463 0.0034 0.0938 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0323 2.0739 2.1225 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8311 1.8489 1.8403 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8075 0.4570 2.3929 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0437 0.6255 -1.0179 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6983 2.0136 0.1739 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0090 -0.9353 1.0350 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6629 0.4648 2.0477 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4541 0.7749 1.2528 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6204 -2.7396 -1.1086 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9803 -1.6905 -1.5052 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8502 -2.2542 0.1592 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6890 0.3821 -0.4828 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7012 -0.3063 -2.6183 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4322 -1.8699 -2.3307 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4162 -1.0439 -2.4602 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6782 -2.6402 -2.4994 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2133 -3.0032 -0.3533 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1390 -0.9932 2.1760 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2570 0.0654 2.0126 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7290 1.5107 0.3960 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9297 1.1192 1.6139 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9681 0.4672 -1.2225 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6374 -1.6198 0.9504 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0459 -2.2247 -1.9609 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8017 -2.9272 -0.5133 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4967 -1.5402 -1.6052 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7123 0.2413 2.0449 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7452 2.0149 1.8117 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9735 -0.0406 1.6587 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8827 1.5944 2.4362 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9700 2.6917 0.2477 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9976 1.5500 -1.8248 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8863 0.2041 -1.0791 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1483 2.3960 0.2410 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6127 3.0793 0.1478 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2460 2.4585 -1.4008 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4756 2.4304 -1.0712 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4418 -2.4112 2.3388 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4332 -3.0926 0.9164 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2630 -3.3883 1.1046 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2501 1.1251 -1.0829 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4652 -1.7155 2.1459 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 0 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 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 21 27 1 0 13 28 1 0 7 29 1 0 6 30 1 0 13 9 1 0 17 12 1 0 21 16 1 0 25 20 1 0 1 31 1 0 1 32 1 0 1 33 1 0 2 34 1 0 3 35 1 0 3 36 1 0 3 37 1 0 4 38 1 0 4 39 1 0 5 40 1 0 5 41 1 0 6 42 1 0 8 43 1 0 8 44 1 0 8 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 11 49 1 0 11 50 1 0 12 51 1 0 14 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 16 56 1 0 17 57 1 0 18 58 1 0 18 59 1 0 19 60 1 0 22 61 1 0 22 62 1 0 23 63 1 0 23 64 1 0 24 65 1 0 25 66 1 0 25 67 1 0 26 68 1 0 27 69 1 0 27 70 1 0 27 71 1 0 28 72 1 0 28 73 1 0 28 74 1 0 29 75 1 0 30 76 1 0 M END

Standard InCHIKey	ISBSSBGEYIBVTO-TYKWNDPBSA-N
Standard InCHI	InChI=1S/C27H46O3/c1-17(2)6-11-24(29)27(5,30)23-10-9-21-20-8-7-18-16-19(28)12-14-25(18,3)22(20)13-15-26(21,23)4/h7,17,19-24,28-30H,6,8-16H2,1-5H3/t19-,20-,21-,22-,23-,24+,25-,26-,27+/m0/s1
SMILES	CC(C)CCC(C(C)(C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	418.34	Volume:	465.056 ? Van der Waals volume.
Dense:	0.9	LogP:	4.612 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.365 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.434 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	20.0
TPSA:	60.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.519	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.567	Fsp³:	0.926
MCE-18:	74.731 ? 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:	0.154	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:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.405	Promiscuous compounds:	0.005

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.831	MDCK Permeability:	-4.726
Pgp-inhibitor:	0.0	Pgp-substrate:	0.31
PAMPA:	0.666 ? 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):	0.01
20% Bioavailability (F20%):	0.016	30% Bioavailability (F30%):	0.214
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.92	MRP1:	0.997
Plasma Protein Binding (PPB):	80.108%	Volume Distribution (VD):	-0.023
Fu:	21.456% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.001
OATP1B3 inhibitor:	0.135	BCRP inhibitor:	0.036
BSEP inhibitor:	0.178

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.079	CYP2C19-substrate:	0.006
CYP2C9-inhibitor:	0.535	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.718	CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	0.033	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.003	CYP2C8-inhibitor:	0.73
HLM stability:	0.904 ? 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):

16.507

Half-life (T1/2):

1.197

ADMET: Toxicity

hERG Blockers:	0.253	hERG Blockers (10um):	0.65
Human Hepatotoxicity (H-HT):	0.655	Drug-induced Liver Injury (DILI):	0.065
AMES Toxicity:	0.103	Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.81	Skin Sensitization:	0.105
Carcinogencity:	0.458	Eye Corrosion:	0.001
Eye Irritation:	0.139	Respiratory Toxicity:	0.642
Drug-induced Neurotoxicity:	0.175	Ototoxicity:	0.881
Hematotoxicity:	0.101	Drug-induced Nephrotoxicity:	0.186
Genotoxicity:	0.002	RPMI-8226 Immunitoxicity:	0.039
A549 Cytotoxicity:	0.22	Hek293 Cytotoxicity:	0.352
BCF:	2.194 ? 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:	4.685 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.916 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.368 ? 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
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1172/JCI16309]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1371/journal.pone.0115359]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10557354]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11034610]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11419736]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11530998]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1175644]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12391014]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12812989]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12840027]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12878451]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15084647]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1521032]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15230696]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15314235]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16112079]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16770722]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1687010]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17116739]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17875433]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18311922]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18544912]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18799520]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425150]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19961175]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506249]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20601097]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	bile	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	faeces	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	urine	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20876113]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[21798258]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2268561]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22711758]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23315938]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23717534]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23752203]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23810710]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23811455]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23868375]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23919613]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24101735]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24399466]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24494566]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24558969]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24816727]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25114169]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25181601]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25293588]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25644343]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26236990]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27471436]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[3179836]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[347637]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4696527]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[5432584]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6121420]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6780563]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8600370]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987136]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9192820]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9800648]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO20338	Mus musculus	Species	Muridae	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
IC50	1
Ki	3

Activity Type	# Activity
Individual protein	1
Single protein	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3064	Individual protein	Ecdysone receptor	Drosophila melanogaster	IC50	=	41686.94	nM	PMID[19631551]
NPT28321	Single protein	Oxysterol-binding protein 1	Homo sapiens	Ki	>	30000.0	nM	PMID[36916802]
NPT29855	Single protein	Oxysterol-binding protein 2	Homo sapiens	Ki	>	15000.0	nM	PMID[36916802]

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 NPC328714 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	22618
0.1-0.2	23717
0.2-0.3	3194
0.3-0.4	212
0.4-0.5	56
0.5-0.6	28
0.6-0.7	26
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
0.7321	Intermediate Similarity	NPC318495
0.7037	Intermediate Similarity	NPC600590
0.6909	Remote Similarity	NPC154330
0.6607	Remote Similarity	NPC136188
0.6607	Remote Similarity	NPC28657
0.6545	Remote Similarity	NPC162742
0.6545	Remote Similarity	NPC304309
0.6545	Remote Similarity	NPC470228
0.6491	Remote Similarity	NPC113733
0.6491	Remote Similarity	NPC198968
0.6429	Remote Similarity	NPC22105
0.6429	Remote Similarity	NPC221758
0.6429	Remote Similarity	NPC34019
0.6429	Remote Similarity	NPC107059
0.6379	Remote Similarity	NPC241290
0.6379	Remote Similarity	NPC164840
0.6379	Remote Similarity	NPC484739
0.6379	Remote Similarity	NPC209944
0.6379	Remote Similarity	NPC264245
0.6379	Remote Similarity	NPC155986
0.6316	Remote Similarity	NPC474216
0.623	Remote Similarity	NPC240650
0.6207	Remote Similarity	NPC230301
0.6207	Remote Similarity	NPC285893
0.6207	Remote Similarity	NPC134847
0.6167	Remote Similarity	NPC33913
0.6102	Remote Similarity	NPC51014
0.6	Remote Similarity	NPC321381
0.5968	Remote Similarity	NPC243985
0.5968	Remote Similarity	NPC473943
0.5968	Remote Similarity	NPC280710
0.5902	Remote Similarity	NPC472265
0.5902	Remote Similarity	NPC59453
0.5818	Remote Similarity	NPC96319
0.5806	Remote Similarity	NPC603646
0.5763	Remote Similarity	NPC328313
0.5714	Remote Similarity	NPC474668
0.5714	Remote Similarity	NPC155011
0.5625	Remote Similarity	NPC474164
0.5625	Remote Similarity	NPC47761
0.5625	Remote Similarity	NPC488870
0.5606	Remote Similarity	NPC601043
0.5606	Remote Similarity	NPC605412
0.5455	Remote Similarity	NPC474349
0.541	Remote Similarity	NPC76879
0.5397	Remote Similarity	NPC1272
0.5397	Remote Similarity	NPC470614
0.5333	Remote Similarity	NPC151519
0.5312	Remote Similarity	NPC477522
0.5294	Remote Similarity	NPC5985
0.5286	Remote Similarity	NPC309493
0.5246	Remote Similarity	NPC20688
0.5224	Remote Similarity	NPC474189
0.5139	Remote Similarity	NPC59530
0.507	Remote Similarity	NPC235126
0.507	Remote Similarity	NPC242419

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC328714 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7380
0.1-0.2	1606
0.2-0.3	146
0.3-0.4	11
0.4-0.5	2
0.5-0.6	2
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6607	Remote Similarity	NPD6942	Phase 4
0.6429	Remote Similarity	NPD4786	Phase 1
0.6207	Remote Similarity	NPD7339	Approved
0.5818	Remote Similarity	NPD3701	Pre-clinical
0.5333	Remote Similarity	NPD3667	Phase 4

Bioactivity similarity

Similar Natural Products in NPASS

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data