NPASS Compound

Natural Product: NPC181964

Natural Product ID	NPC181964
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RCINICONZNJXQF-LYTKHFMESA-N
IUPAC Name	n.a.
Synonyms	7-Epi-Taxol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL503883
PubChem CID	184492
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes 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 113119 0 0 0 0 0 0 0 0999 V2000 -0.2413 -3.0696 -5.1335 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8388 -1.9055 -4.4499 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3345 -0.9798 -5.1134 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8736 -1.7935 -3.0546 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4282 -0.7145 -2.4543 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7993 -1.2720 -1.9502 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2797 -1.6983 -2.9725 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6816 -1.4778 -0.8168 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4694 -2.9766 -0.4805 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1176 -1.4529 -1.4515 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0642 -0.6329 -2.6261 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2256 -0.9893 -0.6626 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1623 -0.7379 0.8059 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7785 -1.2890 1.3149 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8476 -0.6198 0.3382 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9504 0.2693 1.0654 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5816 0.4446 0.5682 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3779 1.2541 -0.6736 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8395 0.0702 -1.4398 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2984 -0.3427 -0.9498 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1123 -1.1696 -1.8458 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7645 -0.0376 0.4492 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9281 0.6952 0.4976 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0793 0.1596 1.0359 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0714 -1.0302 1.5039 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3794 0.8644 1.1260 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4959 -0.0223 0.5060 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7483 0.7583 0.8397 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5552 0.3038 1.8400 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7007 1.0101 2.1446 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0418 2.1661 1.4549 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1930 2.5977 0.4412 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0496 1.8933 0.1366 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2452 -0.1590 -0.8129 N 0 0 0 0 0 0 0 0 0 0 0 0 5.5321 -0.7544 -1.8326 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5142 -1.8037 -1.9983 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6830 -2.3751 -3.2665 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6210 -3.3822 -3.4545 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4122 -3.8594 -2.4363 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2465 -3.3028 -1.2059 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3036 -2.2853 -0.9999 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8044 -0.3671 -3.0246 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3825 2.1042 0.5256 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3590 0.4990 1.3625 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3150 2.3131 -0.6646 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5397 1.8641 -1.3506 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4385 -1.0020 0.3286 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5048 1.6240 1.1451 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6718 2.3121 2.3014 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3026 1.7332 3.3661 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2430 3.6403 2.3149 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7045 4.2562 1.1902 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2406 5.5413 1.2003 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3157 6.2324 2.3859 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8578 5.6313 3.5288 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3283 4.3602 3.5138 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5731 -2.4823 1.1082 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6661 -1.7189 1.6561 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7068 -0.9663 2.6607 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8082 -1.4224 3.5885 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9511 -2.2410 3.2456 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7872 -0.9922 5.0265 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1108 -3.8298 -4.4084 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0146 -3.5371 -5.7767 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5670 -2.7044 -5.7896 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7926 0.0130 -3.2479 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1645 -3.6272 -1.0458 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3506 -3.1672 0.5758 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4810 -3.3470 -0.9193 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3058 -2.4360 -1.9201 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5131 0.2150 -2.4647 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6351 -0.0023 -1.0656 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1463 -1.6343 -0.8111 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3677 0.2625 1.1945 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5533 0.2031 -0.1345 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8268 0.0414 2.1343 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9821 -2.2534 -1.7645 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1713 -1.0239 -1.4533 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2257 -0.7588 -2.8645 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9885 -1.0415 0.8723 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7089 1.0062 2.1880 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5140 -0.9748 1.1047 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3100 -0.6065 2.4017 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3574 0.6623 2.9413 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9417 2.7382 1.6800 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4394 3.4930 -0.1078 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3778 2.2314 -0.6659 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0756 -2.0156 -4.0690 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7242 -3.8005 -4.4469 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1249 -4.6488 -2.6566 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8429 -3.6451 -0.3824 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2291 -1.8929 -0.0149 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9579 0.1525 -2.8460 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5526 2.1898 0.0067 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0788 1.4412 1.8481 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4732 -0.1684 2.2783 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6646 3.2901 -1.1463 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5238 2.0678 -1.3913 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0435 2.6700 0.2854 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8847 2.7353 -0.7993 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1059 2.3637 -2.2929 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2643 1.2181 -1.8151 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4240 -1.4401 1.1822 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6879 3.7720 0.2261 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6066 6.0316 0.3098 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7375 7.2544 2.4198 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9207 6.1899 4.4751 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9858 3.9370 4.4291 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4530 -3.3300 1.8451 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9833 -2.8802 0.2228 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4723 -0.1404 5.1203 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7720 -0.6779 5.3417 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0600 -1.8678 5.6461 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 6 8 1 0 8 9 1 1 8 10 1 0 10 11 1 0 10 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 20 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 27 34 1 0 34 35 2 3 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 35 42 1 0 26 43 1 0 22 44 1 0 18 45 1 0 18 46 1 0 17 47 1 6 16 48 1 0 48 49 1 0 49 50 2 0 49 51 1 0 51 52 2 0 52 53 1 0 53 54 2 0 54 55 1 0 55 56 2 0 14 57 1 0 57 58 1 0 14 59 1 1 59 60 1 0 60 61 2 0 60 62 1 0 19 5 1 0 33 28 1 0 41 36 1 0 56 51 1 0 15 8 1 0 44 17 1 0 58 13 1 0 1 63 1 0 1 64 1 0 1 65 1 0 5 66 1 6 9 67 1 0 9 68 1 0 9 69 1 0 10 70 1 6 11 71 1 0 12 72 1 0 12 73 1 0 13 74 1 6 15 75 1 6 16 76 1 1 21 77 1 0 21 78 1 0 21 79 1 0 22 80 1 1 26 81 1 1 27 82 1 1 29 83 1 0 30 84 1 0 31 85 1 0 32 86 1 0 33 87 1 0 37 88 1 0 38 89 1 0 39 90 1 0 40 91 1 0 41 92 1 0 42 93 1 0 43 94 1 0 44 95 1 0 44 96 1 0 45 97 1 0 45 98 1 0 45 99 1 0 46100 1 0 46101 1 0 46102 1 0 47103 1 0 52104 1 0 53105 1 0 54106 1 0 55107 1 0 56108 1 0 57109 1 0 57110 1 0 62111 1 0 62112 1 0 62113 1 0 M END

Standard InCHIKey	RCINICONZNJXQF-LYTKHFMESA-N
Standard InCHI	InChI=1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32+,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1
SMILES	CC(=O)O[C@H]1C(=O)[C@]2(C)[C@H](O)C[C@@H]3[C@]([C@H]2[C@@H]([C@]2(C(C1=C(C)[C@@H](OC(=O)[C@@H]([C@H](c1ccccc1)N=C(c1ccccc1)O)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	853.33	Volume:	853.449 ? Van der Waals volume.
Dense:	1.0	LogP:	2.591 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.562 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.192 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	44.0
TPSA:	224.78 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	4.0	Rings:	7.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.073	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.121	Fsp³:	0.447
MCE-18:	175.882 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.973	Fluc inhibitor:	0.01 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.037 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.393 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.01	Promiscuous compounds:	0.054

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.5	MDCK Permeability:	-5.002
Pgp-inhibitor:	0.169	Pgp-substrate:	1.0
PAMPA:	1.0 ? 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):	0.001
20% Bioavailability (F20%):	0.976	30% Bioavailability (F30%):	0.987
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	93.866%	Volume Distribution (VD):	-0.027
Fu:	5.125% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.0
BSEP inhibitor:	0.228

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.542
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.837 ? 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):

2.535

Half-life (T1/2):

3.336

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.091
Human Hepatotoxicity (H-HT):	0.986	Drug-induced Liver Injury (DILI):	0.997
AMES Toxicity:	0.943	Rat Oral Acute Toxicity:	0.68
Maximum Recommended Daily Dose:	0.987	Skin Sensitization:	1.0
Carcinogencity:	0.103	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.05
Drug-induced Neurotoxicity:	0.995	Ototoxicity:	0.72
Hematotoxicity:	0.803	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.376
A549 Cytotoxicity:	0.94	Hek293 Cytotoxicity:	0.787
BCF:	0.518 ? 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:	3.48 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.965 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.255 ? 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]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[14987066]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844936]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974623]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[15974623]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	needles	Himalayan	n.a.	PMID[16480866]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955887]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[20426456]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23707257]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Stem Bark	n.a.	n.a.	PMID[28240909]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28581744]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2878063]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7130988]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264680]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	bark	n.a.	n.a.	PMID[7623034]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392886]
NPO23313	Dioscorea althaeoides	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]
NPO27817	Stephania hernandifolia	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4824	Cocculus trilobus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31560	Dioscorea hypoglauca	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]
NPO27509	Dioscorea zingiberensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31560	Dioscorea hypoglauca	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27817	Stephania hernandifolia	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4824	Cocculus trilobus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15018	Dioscorea collettii	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]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15018.1	Dioscorea collettii var. hypoglauca	Varieties	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27509	Dioscorea zingiberensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27817	Stephania hernandifolia	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4824	Cocculus trilobus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23313	Dioscorea althaeoides	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]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27817	Stephania hernandifolia	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4824	Cocculus trilobus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11351	Stephania japonica	Species	Menispermaceae	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]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31560	Dioscorea hypoglauca	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27509	Dioscorea zingiberensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23720	Taxus wallichiana	Species	Taxaceae	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]
NPO15018	Dioscorea collettii	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[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[UNPD]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4824	Cocculus trilobus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27817	Stephania hernandifolia	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15018	Dioscorea collettii	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27064	Taxus brevifolia	Species	Taxaceae	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
ED50	2
IC50	4

Activity Type	# Activity
Cell line	4
Organism	2

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
NPT91	Cell line	KB	Homo sapiens	ED50	=	3.0	10'-5 ug/ml	DOI[10.1021/np50067a001]
NPT91	Cell line	KB	Homo sapiens	IC50	=	0.0015	ug.mL-1	PMID[14987066]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	0.05	nM	PMID[28240909]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC50	>	100000.0	nM	PMID[32527458]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC50	=	71500.0	nM	PMID[32527458]

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 NPC181964 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	11138
0.1-0.2	36539
0.2-0.3	2044
0.3-0.4	69
0.4-0.5	10
0.5-0.6	15
0.6-0.7	11
0.7-0.8	3
0.8-0.85	19
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC208553
1.0	High Similarity	NPC307628
0.8542	High Similarity	NPC471623
0.8454	Intermediate Similarity	NPC33372
0.8454	Intermediate Similarity	NPC67246
0.8454	Intermediate Similarity	NPC324251
0.8454	Intermediate Similarity	NPC206211
0.8367	Intermediate Similarity	NPC487360
0.8367	Intermediate Similarity	NPC479182
0.8367	Intermediate Similarity	NPC479180
0.8367	Intermediate Similarity	NPC471629
0.8367	Intermediate Similarity	NPC306001
0.8351	Intermediate Similarity	NPC453588
0.8247	Intermediate Similarity	NPC321072
0.8247	Intermediate Similarity	NPC215892
0.8247	Intermediate Similarity	NPC242662
0.8218	Intermediate Similarity	NPC487361
0.82	Intermediate Similarity	NPC275170
0.8163	Intermediate Similarity	NPC191193
0.8119	Intermediate Similarity	NPC486061
0.8119	Intermediate Similarity	NPC486060
0.8061	Intermediate Similarity	NPC327699
0.7451	Intermediate Similarity	NPC603171
0.7407	Intermediate Similarity	NPC116862
0.732	Intermediate Similarity	NPC603140
0.7115	Intermediate Similarity	NPC453583
0.7115	Intermediate Similarity	NPC473400
0.7087	Intermediate Similarity	NPC36607
0.7019	Intermediate Similarity	NPC102167
0.7019	Intermediate Similarity	NPC478328
0.7019	Intermediate Similarity	NPC488127
0.7009	Intermediate Similarity	NPC471606
0.6981	Remote Similarity	NPC478329
0.6887	Remote Similarity	NPC471754
0.6887	Remote Similarity	NPC479183
0.6887	Remote Similarity	NPC479181
0.6857	Remote Similarity	NPC473490
0.6562	Remote Similarity	NPC155329
0.6562	Remote Similarity	NPC114357
0.6496	Remote Similarity	NPC479184
0.6404	Remote Similarity	NPC289383
0.6379	Remote Similarity	NPC472391
0.6325	Remote Similarity	NPC479185
0.596	Remote Similarity	NPC605573
0.5893	Remote Similarity	NPC317882
0.5856	Remote Similarity	NPC473300
0.5631	Remote Similarity	NPC259144
0.561	Remote Similarity	NPC472375
0.5574	Remote Similarity	NPC479173
0.5481	Remote Similarity	NPC219419
0.5447	Remote Similarity	NPC479186
0.5243	Remote Similarity	NPC197037
0.5243	Remote Similarity	NPC229545
0.5243	Remote Similarity	NPC248265
0.5243	Remote Similarity	NPC134685
0.5192	Remote Similarity	NPC488128
0.5096	Remote Similarity	NPC91730
0.5048	Remote Similarity	NPC217918

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC181964 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3211
0.1-0.2	5772
0.2-0.3	154
0.3-0.4	0
0.4-0.5	4
0.5-0.6	1
0.6-0.7	3
0.7-0.8	3
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD8485	Phase 4
0.8958	High Similarity	NPD8486	Phase 1
0.7184	Intermediate Similarity	NPD8424	Phase 3
0.7019	Intermediate Similarity	NPD8360	Approved
0.7019	Intermediate Similarity	NPD8361	Phase 4
0.6636	Remote Similarity	NPD8435	Phase 4
0.6581	Remote Similarity	NPD8462	Phase 2
0.6574	Remote Similarity	NPD8368	Phase 2
0.5042	Remote Similarity	NPD8407	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