NPASS Compound

Natural Product: NPC10476

Natural Product ID	NPC10476
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(3S,5R,6R,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-Ethyl-6-Methylheptan-2-Yl)-10,13-Dimethylhexadecahydro-1H-Cyclopenta[A]Phenanthrene-3,5,6-Triol
IUPAC Name	(3S,5R,6R,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,5,6-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1278178
PubChem CID	3036251
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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 84 87 0 0 0 0 0 0 0 0999 V2000 7.5764 -0.9487 0.0805 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2075 -0.6732 0.5685 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3259 0.1383 -0.2967 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9825 -0.3383 -1.6429 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2063 -0.4931 -2.5398 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1517 -1.5928 -1.7263 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1657 0.7406 0.5012 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3018 -0.2634 1.1551 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1959 0.1553 2.0081 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0674 0.9513 1.6106 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1667 2.3167 1.0759 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2677 2.6327 0.5804 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0393 1.3898 0.8495 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0497 0.3202 0.6650 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5596 0.2314 -0.7169 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5258 -0.9602 1.1953 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6373 -1.3488 0.2343 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6813 -0.2981 0.2691 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2054 1.1032 -0.0146 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3096 2.0608 0.3970 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6345 1.7232 -0.2258 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9793 0.2643 -0.1329 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8775 -0.6485 -0.6012 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5782 -0.5521 -2.0550 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2753 -2.0572 -0.2589 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6647 -2.4244 -0.5827 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4991 -1.3993 -1.2461 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2881 0.0026 -0.8015 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4288 -1.4802 -2.6577 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1581 -0.0153 1.2424 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7489 2.2244 -1.5244 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7517 0.7581 3.3432 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1275 -0.0075 -0.1189 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1268 -1.4357 0.9536 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7039 -1.6356 -0.7450 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7121 -1.6062 0.9556 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3404 -0.0695 1.5229 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9597 1.0952 -0.5003 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3492 0.4675 -2.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4189 -1.5551 -2.7135 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9700 -0.0911 -3.5739 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0632 0.1241 -2.2181 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0745 -1.3832 -1.8846 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3430 -2.3338 -0.9566 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4553 -2.1060 -2.6936 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5338 1.5365 1.1439 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5629 1.2523 -0.3097 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9391 -1.0599 0.4614 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0034 -0.8616 1.8372 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7570 -0.8308 2.4286 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3986 1.0905 2.5728 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4398 3.0551 1.8856 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8014 2.5366 0.2393 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2806 2.9673 -0.4588 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6569 3.4380 1.2106 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3325 1.3427 1.9212 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0034 -0.7723 -0.8819 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3044 0.9821 -0.9529 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2477 0.3433 -1.4736 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0167 -0.7357 2.1628 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2047 -1.7527 1.3565 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2573 -1.5904 -0.7683 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0780 -2.2827 0.6407 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0904 -0.2717 1.3224 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9617 1.3011 -1.0598 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0143 3.0628 0.0219 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3638 2.1409 1.5025 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4138 2.2701 0.3732 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2128 0.1467 -2.6198 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6825 -1.5519 -2.5510 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5187 -0.2399 -2.2740 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5235 -2.7353 -0.7296 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1026 -2.1676 0.8521 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6330 -3.3264 -1.2641 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1975 -2.8158 0.3341 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5801 -1.6527 -1.0232 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0960 0.3734 -0.1148 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3413 0.6794 -1.6987 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2220 -0.9709 -2.9838 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1776 0.7889 1.7860 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9237 2.6760 -1.8258 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1435 1.7581 3.1704 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4280 0.0446 3.8131 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8510 0.8497 3.9849 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 4 6 1 0 3 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 6 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 1 0 22 23 1 0 23 24 1 6 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 22 30 1 1 21 31 1 0 9 32 1 0 14 10 1 0 23 18 1 0 19 13 1 0 28 22 1 0 1 33 1 0 1 34 1 0 1 35 1 0 2 36 1 0 2 37 1 0 3 38 1 6 4 39 1 0 5 40 1 0 5 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 6 45 1 0 7 46 1 0 7 47 1 0 8 48 1 0 8 49 1 0 9 50 1 1 10 51 1 1 11 52 1 0 11 53 1 0 12 54 1 0 12 55 1 0 13 56 1 1 15 57 1 0 15 58 1 0 15 59 1 0 16 60 1 0 16 61 1 0 17 62 1 0 17 63 1 0 18 64 1 1 19 65 1 6 20 66 1 0 20 67 1 0 21 68 1 1 24 69 1 0 24 70 1 0 24 71 1 0 25 72 1 0 25 73 1 0 26 74 1 0 26 75 1 0 27 76 1 6 28 77 1 0 28 78 1 0 29 79 1 0 30 80 1 0 31 81 1 0 32 82 1 0 32 83 1 0 32 84 1 0 M END

Standard InCHIKey	VGSSUFQMXBFFTM-METNKUIYSA-N
Standard InCHI	InChI=1S/C29H52O3/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-22-16-26(31)29(32)17-21(30)12-15-28(29,6)25(22)13-14-27(23,24)5/h18-26,30-32H,7-17H2,1-6H3/t19-,20-,21+,22+,23-,24+,25+,26-,27-,28-,29+/m1/s1
SMILES	CC[C@@H](C(C)C)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@H]([C@@]2([C@]1(C)CC[C@@H](C2)O)O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	448.39	Volume:	502.285 ? Van der Waals volume.
Dense:	0.893	LogP:	6.056 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.74 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.379 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	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:	0.454	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.716	Fsp³:	1.0
MCE-18:	77.586 ? 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:	0.623	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? 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:	0.444	Promiscuous compounds:	0.221

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.19	MDCK Permeability:	-4.881
Pgp-inhibitor:	0.0	Pgp-substrate:	0.703
PAMPA:	0.917 ? 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%):	0.057	30% Bioavailability (F30%):	0.402
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.019
Plasma Protein Binding (PPB):	94.747%	Volume Distribution (VD):	0.007
Fu:	7.146% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.079
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.11	CYP2C19-substrate:	0.01
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.011
CYP3A4-inhibitor:	0.996	CYP3A4-substrate:	0.975
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.99
HLM stability:	0.884 ? 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):

6.588

Half-life (T1/2):

1.934

ADMET: Toxicity

hERG Blockers:	0.109	hERG Blockers (10um):	0.267
Human Hepatotoxicity (H-HT):	0.49	Drug-induced Liver Injury (DILI):	0.041
AMES Toxicity:	0.104	Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.615	Skin Sensitization:	0.987
Carcinogencity:	0.538	Eye Corrosion:	0.219
Eye Irritation:	0.947	Respiratory Toxicity:	0.886
Drug-induced Neurotoxicity:	0.013	Ototoxicity:	0.77
Hematotoxicity:	0.169	Drug-induced Nephrotoxicity:	0.652
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.063
A549 Cytotoxicity:	0.286	Hek293 Cytotoxicity:	0.379
BCF:	2.511 ? 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:	4.433 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.31 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.06 ? 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
NPO4562	Lonchocarpus urucu	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10075742]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17548953]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[20166702]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21114277]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21171571]
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	Eukaryota	roots	Xishuangbanna of Yunnan Province, China	n.a.	PMID[21428418]
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	root	n.a.	PMID[21428418]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24675423]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Bako, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Enemore, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Gedo, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Holleta, Ethiopia		PMID[24926420]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29094598]
NPO9740	Dacrycarpus imbricatus	Species	Podocarpaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[32786878]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13876	Cedrela salvadorensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13669	Hertia cheirifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14169	Acrocarpia paniculata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9569	Licaria chrysophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2622	Cheilanthes mysurensis	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO378	Myristica argentea	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4562	Lonchocarpus urucu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1477	Egregia menziesii	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6559	Duddingtonia flagrans	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13443	Doris montereyensis	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9740	Dacrycarpus imbricatus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9234	Cynoctonum wilfordii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO182	Cylas formicarius	Species	Brentidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO790	Cybister confusus	Species	Dytiscidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9094	Citrus reshni	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13178	Ornithoglossum viride	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6017	Artemisia arbuscula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8794	Aconitum fauriei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12521	Sphaeranthus confertifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5280	Rubia tetragona	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14470	Polypodium decumanum	Species	Polypodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14369	Pocillopora eydouxi	Species	Pocilloporidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4700	Pertusaria truncata	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6017	Artemisia arbuscula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6017	Artemisia arbuscula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9740	Dacrycarpus imbricatus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13876	Cedrela salvadorensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6017	Artemisia arbuscula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9740	Dacrycarpus imbricatus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13178	Ornithoglossum viride	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9234	Cynoctonum wilfordii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14169	Acrocarpia paniculata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14470	Polypodium decumanum	Species	Polypodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2622	Cheilanthes mysurensis	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12521	Sphaeranthus confertifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4700	Pertusaria truncata	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14369	Pocillopora eydouxi	Species	Pocilloporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5280	Rubia tetragona	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9569	Licaria chrysophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13443	Doris montereyensis	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9094	Citrus reshni	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO378	Myristica argentea	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO790	Cybister confusus	Species	Dytiscidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1477	Egregia menziesii	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4562	Lonchocarpus urucu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13669	Hertia cheirifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8794	Aconitum fauriei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO182	Cylas formicarius	Species	Brentidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6559	Duddingtonia flagrans	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	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

Activity Type	# Activity
Cell line	1

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
NPT139	Cell line	HT-29	Homo sapiens	IC50	>	50000.0	nM	PMID[20931970]

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 NPC10476 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	26180
0.1-0.2	21871
0.2-0.3	1547
0.3-0.4	206
0.4-0.5	33
0.5-0.6	13
0.6-0.7	1
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8913	High Similarity	NPC192501
0.8163	Intermediate Similarity	NPC196136
0.78	Intermediate Similarity	NPC228994
0.7358	Intermediate Similarity	NPC486085
0.7273	Intermediate Similarity	NPC60018
0.7273	Intermediate Similarity	NPC202688
0.65	Remote Similarity	NPC486086
0.5965	Remote Similarity	NPC470360
0.5763	Remote Similarity	NPC85095
0.5741	Remote Similarity	NPC148174
0.5593	Remote Similarity	NPC67657
0.541	Remote Similarity	NPC470361
0.5385	Remote Similarity	NPC486638
0.5238	Remote Similarity	NPC154043
0.5172	Remote Similarity	NPC158208
0.5167	Remote Similarity	NPC230301
0.5167	Remote Similarity	NPC243027
0.5152	Remote Similarity	NPC219516
0.5082	Remote Similarity	NPC211135
0.507	Remote Similarity	NPC293609

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC10476 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7535
0.1-0.2	1483
0.2-0.3	118
0.3-0.4	12
0.4-0.5	1
0.5-0.6	1
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
0.5167	Remote Similarity	NPD7339	Approved

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