NPASS Compound

Natural Product: NPC76594

Natural Product ID	NPC76594
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CZCROZIJKBXZDP-CINKSSDWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	50989896
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 77 82 0 0 0 0 0 0 0 0999 V2000 -8.7499 0.6770 -0.3367 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2732 0.4762 -0.4025 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7196 -0.1915 0.8630 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3136 -0.5890 0.4746 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5402 0.6564 0.1537 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5019 0.2422 -0.9120 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2486 1.3190 -1.8914 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4449 -0.1679 -0.0253 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5154 1.0337 0.9602 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3844 0.6166 1.8394 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3845 0.5196 0.7441 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9592 -0.0051 0.9903 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6573 0.7034 2.1278 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0565 0.2192 2.1820 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7160 -0.1771 1.1067 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1142 -0.6429 1.2665 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0028 0.0760 0.3050 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4452 0.3174 -1.0517 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0036 0.7683 -1.0715 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1269 -0.1768 -0.2525 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3035 -1.5553 -0.8448 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7165 0.3159 -0.2894 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0406 -0.1377 -1.5436 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4514 0.0523 -1.5834 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0691 -0.3565 -0.2948 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6942 -1.8242 -0.0266 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2455 -0.5857 0.1879 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4486 -0.0423 0.5540 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4334 1.1347 1.0288 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7382 -0.8003 0.4036 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7826 0.9156 1.3325 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2273 1.7538 -0.1478 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4783 1.7130 -0.6313 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1635 0.4266 -1.3535 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1966 -0.0971 0.3390 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0283 1.6784 -0.0119 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0104 -0.2442 -1.2323 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6640 0.5372 1.6822 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3093 -1.0899 1.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8869 -1.1760 1.3111 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3224 -1.2733 -0.4039 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8962 -0.6481 -1.4850 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7602 2.2138 -1.5077 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7460 0.8673 -2.7805 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2442 1.6690 -2.2975 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8560 -1.0062 0.6232 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2186 1.9617 0.4412 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6166 -0.3619 2.3002 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1145 1.3853 2.5905 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2961 1.5526 0.2960 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9906 -1.0854 1.2237 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6179 1.8051 1.9960 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1258 0.4041 3.0632 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5088 0.2125 3.1777 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2305 -1.7439 1.2461 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4933 -0.3583 2.2971 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2432 1.0887 0.7444 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5535 -0.5440 -1.7493 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0359 1.1453 -1.5198 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6505 0.7437 -2.1142 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8743 1.8070 -0.7028 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3242 -1.9192 -0.5432 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6004 -2.2941 -0.4158 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3236 -1.5499 -1.9558 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7273 1.4466 -0.3332 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3457 -1.1565 -1.8761 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4431 0.5285 -2.3690 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6190 1.1558 -1.7105 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8383 -0.5414 -2.4227 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7886 -2.0608 1.0496 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2165 -2.1405 -0.5076 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5309 -2.4050 -0.5177 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0563 -0.6907 -0.6565 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5337 -0.3497 1.0201 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6024 -1.8753 0.6208 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5581 1.9480 -1.7351 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0617 2.5607 -0.1570 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 6 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 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 17 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 9 31 1 0 5 32 1 6 32 33 1 0 33 2 1 0 31 5 1 0 25 8 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 6 3 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 6 42 1 6 7 43 1 0 7 44 1 0 7 45 1 0 8 46 1 0 9 47 1 6 10 48 1 0 10 49 1 0 11 50 1 6 12 51 1 1 13 52 1 0 13 53 1 0 14 54 1 0 16 55 1 0 16 56 1 0 17 57 1 1 18 58 1 0 18 59 1 0 19 60 1 0 19 61 1 0 21 62 1 0 21 63 1 0 21 64 1 0 22 65 1 6 23 66 1 0 23 67 1 0 24 68 1 0 24 69 1 0 26 70 1 0 26 71 1 0 26 72 1 0 30 73 1 0 30 74 1 0 30 75 1 0 33 76 1 0 33 77 1 0 M END

Standard InCHIKey	CZCROZIJKBXZDP-CINKSSDWSA-N
Standard InCHI	InChI=1S/C29H44O4/c1-17-8-13-29(31-16-17)18(2)26-25(33-29)15-24-22-7-6-20-14-21(32-19(3)30)9-11-27(20,4)23(22)10-12-28(24,26)5/h6,17-18,21-26H,7-16H2,1-5H3/t17-,18+,21+,22-,23+,24+,25+,26?,27+,28+,29-/m1/s1
SMILES	C[C@@H]1CC[C@@]2([C@@H](C)C3[C@H](C[C@H]4[C@@H]5CC=C6C[C@H](CC[C@]6(C)[C@H]5CC[C@]34C)OC(=O)C)O2)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	456.32	Volume:	488.689 ? Van der Waals volume.
Dense:	0.934	LogP:	4.884 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.905 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.602 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	31.0
TPSA:	44.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	0.0	Rings:	6.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.344	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.264	Fsp³:	0.897
MCE-18:	139.255 ? 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:	0.902	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? 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:	0.295	Promiscuous compounds:	0.785

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.844	MDCK Permeability:	-4.823
Pgp-inhibitor:	0.997	Pgp-substrate:	0.291
PAMPA:	0.034 ? 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%):	0.771	30% Bioavailability (F30%):	0.705
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026	MRP1:	0.979
Plasma Protein Binding (PPB):	95.408%	Volume Distribution (VD):	0.589
Fu:	5.421% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.74
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.885	CYP1A2-substrate:	0.076
CYP2C19-inhibitor:	0.547	CYP2C19-substrate:	0.02
CYP2C9-inhibitor:	0.173	CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.591
CYP3A4-inhibitor:	0.138	CYP3A4-substrate:	0.962
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	0.976
HLM stability:	0.961 ? 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):

9.265

Half-life (T1/2):

0.239

ADMET: Toxicity

hERG Blockers:	0.077	hERG Blockers (10um):	0.257
Human Hepatotoxicity (H-HT):	0.401	Drug-induced Liver Injury (DILI):	0.733
AMES Toxicity:	0.845	Rat Oral Acute Toxicity:	0.537
Maximum Recommended Daily Dose:	0.814	Skin Sensitization:	0.994
Carcinogencity:	0.959	Eye Corrosion:	0.013
Eye Irritation:	0.345	Respiratory Toxicity:	0.549
Drug-induced Neurotoxicity:	0.187	Ototoxicity:	0.329
Hematotoxicity:	0.444	Drug-induced Nephrotoxicity:	0.734
Genotoxicity:	0.354	RPMI-8226 Immunitoxicity:	0.13
A549 Cytotoxicity:	0.955	Hek293 Cytotoxicity:	0.871
BCF:	2.223 ? 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:	3.933 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.84 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.636 ? 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
NPO15018.1	Dioscorea collettii var. hypoglauca	Varieties	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075765]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23707257]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27509	Dioscorea zingiberensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17650	Dioscorea septemloba	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15018	Dioscorea collettii	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15018.1	Dioscorea collettii var. hypoglauca	Varieties	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9436	Dioscorea parviflora	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9089	Dioscorea panthaica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14297	Dioscorea gracillima	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9436	Dioscorea parviflora	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12396	Smilax menispermoidea	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9089	Dioscorea panthaica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14297	Dioscorea gracillima	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15018	Dioscorea collettii	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17650	Dioscorea septemloba	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27509	Dioscorea zingiberensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9436	Dioscorea parviflora	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15018	Dioscorea collettii	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17650	Dioscorea septemloba	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27509	Dioscorea zingiberensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12396	Smilax menispermoidea	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21651	Cheilocostus speciosus	Species	Costaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14297	Dioscorea gracillima	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15018.1	Dioscorea collettii var. hypoglauca	Varieties	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9089	Dioscorea panthaica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27509	Dioscorea zingiberensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14297	Dioscorea gracillima	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17650	Dioscorea septemloba	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15018	Dioscorea collettii	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12396	Smilax menispermoidea	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9089	Dioscorea panthaica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17650	Dioscorea septemloba	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27509	Dioscorea zingiberensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15018.1	Dioscorea collettii var. hypoglauca	Varieties	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15018	Dioscorea collettii	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17650	Dioscorea septemloba	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21651	Cheilocostus speciosus	Species	Costaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14297	Dioscorea gracillima	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12396	Smilax menispermoidea	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9089	Dioscorea panthaica	Species	Dioscoreaceae	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 NPC76594 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	23424
0.1-0.2	23085
0.2-0.3	2949
0.3-0.4	273
0.4-0.5	76
0.5-0.6	36
0.6-0.7	11
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC100451
0.7143	Intermediate Similarity	NPC235126
0.7143	Intermediate Similarity	NPC242419
0.6962	Remote Similarity	NPC181845
0.6667	Remote Similarity	NPC470613
0.6667	Remote Similarity	NPC470612
0.6267	Remote Similarity	NPC486119
0.625	Remote Similarity	NPC470432
0.625	Remote Similarity	NPC230507
0.625	Remote Similarity	NPC187159
0.6111	Remote Similarity	NPC113044
0.6111	Remote Similarity	NPC283829
0.6111	Remote Similarity	NPC14704
0.6111	Remote Similarity	NPC161676
0.5921	Remote Similarity	NPC177818
0.5914	Remote Similarity	NPC470433
0.5914	Remote Similarity	NPC46190
0.5914	Remote Similarity	NPC171073
0.5914	Remote Similarity	NPC602423
0.5851	Remote Similarity	NPC477809
0.5789	Remote Similarity	NPC300557
0.5769	Remote Similarity	NPC485606
0.5729	Remote Similarity	NPC480555
0.5729	Remote Similarity	NPC150372
0.5714	Remote Similarity	NPC469599
0.5657	Remote Similarity	NPC475333
0.5657	Remote Similarity	NPC224098
0.5657	Remote Similarity	NPC208383
0.5556	Remote Similarity	NPC269297
0.5556	Remote Similarity	NPC222202
0.5514	Remote Similarity	NPC477808
0.5493	Remote Similarity	NPC153987
0.5464	Remote Similarity	NPC6806
0.5417	Remote Similarity	NPC44083
0.5392	Remote Similarity	NPC480554
0.5362	Remote Similarity	NPC609635
0.5361	Remote Similarity	NPC248746
0.5342	Remote Similarity	NPC24556
0.5288	Remote Similarity	NPC480553
0.5288	Remote Similarity	NPC477811
0.5248	Remote Similarity	NPC475550
0.5196	Remote Similarity	NPC309278
0.5195	Remote Similarity	NPC305808
0.5185	Remote Similarity	NPC480556
0.5146	Remote Similarity	NPC194207
0.5146	Remote Similarity	NPC22779
0.5138	Remote Similarity	NPC224314
0.5067	Remote Similarity	NPC248944
0.5067	Remote Similarity	NPC7479
0.5067	Remote Similarity	NPC257296

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC76594 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7053
0.1-0.2	1958
0.2-0.3	121
0.3-0.4	12
0.4-0.5	5
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
0.5067	Remote Similarity	NPD6928	Phase 2

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