NPASS Compound

Natural Product: NPC136464

Natural Product ID	NPC136464
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RXFMCOJBKQMRRX-PZWJQCECSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides 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 122129 0 0 0 0 0 0 0 0999 V2000 1.2919 -1.5364 -1.2774 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6967 -2.8272 -0.6295 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7862 -2.6867 0.3596 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3029 -3.2179 1.7087 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1094 -2.2749 2.0397 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0795 -2.4188 0.9435 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5660 -3.3803 -0.0047 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0940 -2.8841 1.4495 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2390 -2.2438 0.9721 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3581 -3.1456 0.7035 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6165 -2.4233 0.3186 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0065 -1.3623 1.3636 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2324 -2.0421 2.6353 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7578 -1.7818 3.7253 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8026 -0.4277 1.3653 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0746 0.8828 1.9900 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2100 1.6164 1.2649 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9673 0.7012 0.3291 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2352 -0.6702 0.9189 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2082 -0.5479 2.0764 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5359 -0.1361 1.4825 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4023 1.2115 0.8270 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.4194 2.2320 1.9396 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6219 1.4061 -0.0402 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2480 0.4919 -1.2118 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7679 0.6130 -1.3622 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2481 1.3490 -0.1189 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0713 2.6636 -0.4614 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8933 2.7757 -0.5226 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7764 3.1374 -1.8161 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1261 4.5427 -1.9381 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1436 5.2715 -2.9854 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4527 4.9932 -0.6995 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3361 3.9494 0.2331 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6430 -1.1212 1.9571 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5657 -0.9843 2.0985 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2649 -3.1689 2.6880 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0092 -3.1653 -0.0217 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0802 -2.3325 0.1343 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2007 -3.0438 0.8261 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4599 -2.9651 0.0388 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7596 -1.5122 -0.3110 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5018 -0.8850 -0.9012 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7723 0.0173 -2.0646 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7361 0.9203 -1.6349 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1232 1.8800 -2.5203 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9737 3.2834 -1.9729 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7031 3.4187 -0.6450 C 0 0 2 0 0 0 0 0 0 0 0 0 9.8640 2.4434 -0.6056 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3565 2.2308 -2.0264 C 0 0 1 0 0 0 0 0 0 0 0 0 11.5912 1.3544 -1.9383 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1525 1.1694 -3.2032 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4546 1.6089 -2.8464 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9552 2.9896 0.0944 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7975 3.2507 0.3777 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4905 4.1693 -2.9110 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5537 -1.8928 -1.1340 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2683 -0.7846 0.7438 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4544 -3.7731 -1.0920 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3806 -2.6261 2.1478 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5013 -0.6391 -0.6638 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9010 -1.3785 -2.2181 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2526 -1.6175 -1.6212 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0169 -3.5156 -1.4372 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9398 -1.5840 0.5962 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8458 -4.2016 1.5283 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6452 -2.6012 2.9906 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0053 -1.4934 0.3683 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9252 -1.6544 0.0883 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0863 -3.7601 -0.2120 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5688 -3.8532 1.5525 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4158 -1.8758 -0.6399 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4336 -3.1472 0.1920 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9147 -2.9101 2.6415 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5758 -0.2781 0.2742 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1152 1.4828 1.9066 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3567 0.7766 3.0346 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8112 2.2027 1.9484 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6790 2.3564 0.5856 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3351 0.5524 -0.5581 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7532 -1.2723 0.1501 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3739 -1.5787 2.4631 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8581 0.0617 2.9016 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7784 -0.8893 0.7265 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3237 -0.0455 2.2612 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8967 3.1544 1.7499 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4750 2.4237 2.2058 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9693 1.8093 2.8803 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5329 1.0033 0.4713 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8464 0.7564 -2.0846 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5832 -0.5383 -0.9370 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5631 1.2428 -2.2756 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2684 -0.3502 -1.5299 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8983 2.8358 -1.4138 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4745 2.5152 -2.6611 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3026 3.7676 0.7748 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5748 4.3516 0.9700 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7685 -0.3954 1.9099 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6753 -1.4624 2.9724 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3519 -0.6202 3.0167 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1225 -2.3231 3.2081 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7126 -1.4310 0.6876 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9011 -4.1427 0.9288 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2998 -3.2890 0.6808 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5145 -1.5344 -1.1165 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0659 -0.2563 -0.0896 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8777 0.4934 -2.4726 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2424 -0.5377 -2.9304 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5629 1.7880 -3.4597 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9257 3.5173 -1.7992 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1181 4.4522 -0.6153 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5451 1.4820 -0.1613 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7158 3.2061 -2.4302 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2991 0.4043 -1.4468 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2989 1.8467 -1.2193 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1228 2.0708 -3.6572 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9861 2.7186 1.0288 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7252 2.2674 0.5444 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7823 4.7511 -3.3196 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2531 -0.8749 0.7298 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5085 -3.1892 -1.8926 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2801 -3.3615 2.8072 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 1 13 14 2 0 12 15 1 0 15 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 1 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 24 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 15 35 1 0 5 36 1 0 4 37 1 0 3 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 50 53 1 0 49 54 1 0 48 55 1 0 47 56 1 0 43 57 1 0 42 58 1 0 41 59 1 0 40 60 1 0 7 2 1 0 35 9 1 0 57 39 1 0 19 12 1 0 27 22 1 0 34 29 1 0 53 46 1 0 27 18 1 0 1 61 1 0 1 62 1 0 1 63 1 0 2 64 1 6 3 65 1 1 4 66 1 6 5 67 1 1 6 68 1 6 9 69 1 6 10 70 1 0 10 71 1 0 11 72 1 0 11 73 1 0 13 74 1 0 15 75 1 6 16 76 1 0 16 77 1 0 17 78 1 0 17 79 1 0 18 80 1 6 19 81 1 6 20 82 1 0 20 83 1 0 21 84 1 0 21 85 1 0 23 86 1 0 23 87 1 0 23 88 1 0 24 89 1 1 25 90 1 0 25 91 1 0 26 92 1 0 26 93 1 0 28 94 1 0 30 95 1 0 34 96 1 0 34 97 1 0 35 98 1 0 35 99 1 0 36100 1 0 37101 1 0 39102 1 1 40103 1 1 41104 1 1 42105 1 6 43106 1 1 44107 1 0 44108 1 0 46109 1 6 47110 1 1 48111 1 6 49112 1 1 50113 1 6 51114 1 0 51115 1 0 52116 1 0 54117 1 0 55118 1 0 56119 1 0 58120 1 0 59121 1 0 60122 1 0 M END

Standard InCHIKey	RXFMCOJBKQMRRX-PZWJQCECSA-N
Standard InCHI	InChI=1S/C41H62O19/c1-17-35(60-38-33(51)30(48)28(46)25(59-38)15-55-36-32(50)29(47)27(45)24(13-42)58-36)31(49)34(52)37(56-17)57-20-5-9-40(16-43)19(12-20)3-4-23-22(40)6-8-39(2)21(7-10-41(23,39)53)18-11-26(44)54-14-18/h11,16-17,19-25,27-38,42,45-53H,3-10,12-15H2,1-2H3/t17-,19-,20-,21+,22-,23-,24+,25+,27+,28+,29-,30-,31-,32+,33+,34+,35-,36+,37-,38-,39+,40+,41-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1CC[C@@]2(C=O)[C@@H](CC[C@H]3[C@@H]2CC[C@]2(C)[C@H](CC[C@]32O)C2=CC(=O)OC2)C1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	858.39	Volume:	808.345 ? Van der Waals volume.
Dense:	1.062	LogP:	-1.052 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.09 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.928 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	45.0
TPSA:	301.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	10.0	Rings:	8.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.061	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.192	Fsp³:	0.902
MCE-18:	156.538 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.667	Fluc inhibitor:	0.003 ? 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:	0.163	Promiscuous compounds:	0.125

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.872	MDCK Permeability:	-5.087
Pgp-inhibitor:	0.0	Pgp-substrate:	0.996
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):	0.897
20% Bioavailability (F20%):	0.39	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.006
Plasma Protein Binding (PPB):	46.254%	Volume Distribution (VD):	-0.501
Fu:	44.975% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.013
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.02	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.197
HLM stability:	0.001 ? 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):

0.175

Half-life (T1/2):

5.423

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.075
Human Hepatotoxicity (H-HT):	0.664	Drug-induced Liver Injury (DILI):	0.947
AMES Toxicity:	0.989	Rat Oral Acute Toxicity:	0.21
Maximum Recommended Daily Dose:	0.97	Skin Sensitization:	1.0
Carcinogencity:	0.382	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.118
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.996
Hematotoxicity:	0.723	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.888
A549 Cytotoxicity:	0.59	Hek293 Cytotoxicity:	0.96
BCF:	0.538 ? 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:	3.245 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.793 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.858 ? 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
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757709]
NPO2130	Ehretia dicksonii	Species	Ehretiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[10830513]
NPO2130	Ehretia dicksonii	Species	Ehretiaceae	Eukaryota	n.a.	twig	n.a.	PMID[10830513]
NPO2130	Ehretia dicksonii	Species	Ehretiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10830513]
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193039]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17685627]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[21353549]
NPO13504	Lotus japonicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21510636]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	Stems	n.a.	n.a.	PMID[23078294]
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23210623]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23513740]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30379546]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31596079]
NPO11882	Cedrus libani	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32092041]
NPO13076	Cephalaria grossheimii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13504	Lotus japonicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14615	Streptomyces paulus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6179	Aframomum amaniense	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14504	Alectoria divergens	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14200	Aristolochia zollingeriana	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3199	Balanophora involucrata	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1661	Bartramia pomiformis	Species	Bartramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7752	Beilschmiedia anacardioides	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11882	Cedrus libani	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25774	Virola multinervia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10012	Triaenophora rupestris	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10865	Sextonia rubra	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13907	Senecio renardii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14289	Pieris napi	Species	Pieridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12414	Penicillium paxilli	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7169	Nama hispidum	Species	Namaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13701	Melaleuca rhaphiophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3458	Lupinus verbasciformis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10389	Larix cajanderi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12234	Khaya ivorensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12061	Justicia paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12910	Ixeris stolonifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12069	Isaria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2130	Ehretia dicksonii	Species	Ehretiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9669	Dictyopteris acrostichoides	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12585	Craspidospermum verticillatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21498	Coccus ilicis	Species	Coccidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12754	Cerinthe minor	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13907	Senecio renardii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25774	Virola multinervia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3199	Balanophora involucrata	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25774	Virola multinervia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13907	Senecio renardii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14504	Alectoria divergens	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14200	Aristolochia zollingeriana	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13504	Lotus japonicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12910	Ixeris stolonifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13907	Senecio renardii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1661	Bartramia pomiformis	Species	Bartramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12069	Isaria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13701	Melaleuca rhaphiophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12414	Penicillium paxilli	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25774	Virola multinervia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3199	Balanophora involucrata	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2130	Ehretia dicksonii	Species	Ehretiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9669	Dictyopteris acrostichoides	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3458	Lupinus verbasciformis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21498	Coccus ilicis	Species	Coccidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6179	Aframomum amaniense	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12585	Craspidospermum verticillatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12061	Justicia paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13076	Cephalaria grossheimii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12234	Khaya ivorensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14615	Streptomyces paulus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12754	Cerinthe minor	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11882	Cedrus libani	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10865	Sextonia rubra	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10389	Larix cajanderi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7752	Beilschmiedia anacardioides	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7169	Nama hispidum	Species	Namaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10012	Triaenophora rupestris	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14289	Pieris napi	Species	Pieridae	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 NPC136464 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	16169
0.1-0.2	28825
0.2-0.3	3743
0.3-0.4	894
0.4-0.5	92
0.5-0.6	60
0.6-0.7	39
0.7-0.8	0
0.8-0.85	7
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9176	High Similarity	NPC188234
0.8235	Intermediate Similarity	NPC480914
0.8043	Intermediate Similarity	NPC232785
0.8043	Intermediate Similarity	NPC486139
0.8	Intermediate Similarity	NPC236973
0.8	Intermediate Similarity	NPC32177
0.8	Intermediate Similarity	NPC469756
0.8	Intermediate Similarity	NPC275901
0.7935	Intermediate Similarity	NPC125077
0.7889	Intermediate Similarity	NPC30483
0.7889	Intermediate Similarity	NPC470897
0.7857	Intermediate Similarity	NPC486150
0.7629	Intermediate Similarity	NPC486144
0.7629	Intermediate Similarity	NPC486145
0.7629	Intermediate Similarity	NPC486147
0.7629	Intermediate Similarity	NPC475590
0.7629	Intermediate Similarity	NPC486136
0.7629	Intermediate Similarity	NPC486148
0.734	Intermediate Similarity	NPC32793
0.734	Intermediate Similarity	NPC116075
0.7303	Intermediate Similarity	NPC469750
0.7216	Intermediate Similarity	NPC329986
0.7216	Intermediate Similarity	NPC140092
0.7143	Intermediate Similarity	NPC486138
0.7143	Intermediate Similarity	NPC276838
0.7111	Intermediate Similarity	NPC5311
0.7111	Intermediate Similarity	NPC77299
0.7111	Intermediate Similarity	NPC480906
0.7019	Intermediate Similarity	NPC474423
0.701	Intermediate Similarity	NPC486143
0.701	Intermediate Similarity	NPC486135
0.701	Intermediate Similarity	NPC486142
0.701	Intermediate Similarity	NPC486137
0.701	Intermediate Similarity	NPC486149
0.6961	Remote Similarity	NPC475419
0.6915	Remote Similarity	NPC480907
0.6893	Remote Similarity	NPC474908
0.6893	Remote Similarity	NPC486134
0.6893	Remote Similarity	NPC486141
0.6733	Remote Similarity	NPC486131
0.6667	Remote Similarity	NPC486128
0.6635	Remote Similarity	NPC120390
0.6633	Remote Similarity	NPC480910
0.6633	Remote Similarity	NPC480909
0.6566	Remote Similarity	NPC610296
0.6531	Remote Similarity	NPC292467
0.6505	Remote Similarity	NPC479360
0.6505	Remote Similarity	NPC479359
0.65	Remote Similarity	NPC59288
0.6489	Remote Similarity	NPC76572
0.6489	Remote Similarity	NPC193382
0.6465	Remote Similarity	NPC240070
0.6415	Remote Similarity	NPC194716
0.64	Remote Similarity	NPC264336
0.6355	Remote Similarity	NPC486133
0.6344	Remote Similarity	NPC99620
0.6277	Remote Similarity	NPC84987
0.625	Remote Similarity	NPC250556
0.6238	Remote Similarity	NPC475629
0.6214	Remote Similarity	NPC486146
0.62	Remote Similarity	NPC40749
0.6168	Remote Similarity	NPC74259
0.6147	Remote Similarity	NPC488945
0.6147	Remote Similarity	NPC488946
0.6139	Remote Similarity	NPC475556
0.6139	Remote Similarity	NPC311706
0.6139	Remote Similarity	NPC486130
0.6078	Remote Similarity	NPC486127
0.6071	Remote Similarity	NPC486152
0.6042	Remote Similarity	NPC480915
0.602	Remote Similarity	NPC179412
0.602	Remote Similarity	NPC471356
0.6019	Remote Similarity	NPC208193
0.5962	Remote Similarity	NPC469749
0.5943	Remote Similarity	NPC476221
0.5943	Remote Similarity	NPC477709
0.5943	Remote Similarity	NPC479357
0.5938	Remote Similarity	NPC196429
0.5922	Remote Similarity	NPC231518
0.5922	Remote Similarity	NPC488944
0.5794	Remote Similarity	NPC486132
0.5755	Remote Similarity	NPC146857
0.5714	Remote Similarity	NPC17896
0.5714	Remote Similarity	NPC469755
0.5714	Remote Similarity	NPC284406
0.5714	Remote Similarity	NPC197707
0.5714	Remote Similarity	NPC251866
0.5676	Remote Similarity	NPC329675
0.5664	Remote Similarity	NPC488947
0.5607	Remote Similarity	NPC247190
0.5596	Remote Similarity	NPC488943
0.5596	Remote Similarity	NPC488942
0.5588	Remote Similarity	NPC72260
0.5556	Remote Similarity	NPC157376
0.5556	Remote Similarity	NPC142066
0.5556	Remote Similarity	NPC603972
0.5545	Remote Similarity	NPC471353
0.5545	Remote Similarity	NPC305574
0.5536	Remote Similarity	NPC486140
0.551	Remote Similarity	NPC99728
0.551	Remote Similarity	NPC87250
0.551	Remote Similarity	NPC244402
0.551	Remote Similarity	NPC50305
0.5505	Remote Similarity	NPC475219
0.55	Remote Similarity	NPC243196
0.5455	Remote Similarity	NPC219085
0.5431	Remote Similarity	NPC286809
0.5398	Remote Similarity	NPC117445
0.5398	Remote Similarity	NPC308262
0.5377	Remote Similarity	NPC479353
0.5377	Remote Similarity	NPC479354
0.5377	Remote Similarity	NPC608063
0.5354	Remote Similarity	NPC471633
0.5347	Remote Similarity	NPC199428
0.5347	Remote Similarity	NPC109448
0.5347	Remote Similarity	NPC310341
0.5327	Remote Similarity	NPC488941
0.5327	Remote Similarity	NPC488940
0.5278	Remote Similarity	NPC55532
0.5268	Remote Similarity	NPC479358
0.5253	Remote Similarity	NPC158344
0.5243	Remote Similarity	NPC483822
0.5146	Remote Similarity	NPC146456
0.5096	Remote Similarity	NPC277374
0.505	Remote Similarity	NPC473852
0.5049	Remote Similarity	NPC84949
0.5049	Remote Similarity	NPC480562
0.5049	Remote Similarity	NPC74945
0.5049	Remote Similarity	NPC31354
0.5049	Remote Similarity	NPC69576
0.5049	Remote Similarity	NPC604978
0.5044	Remote Similarity	NPC488938
0.5044	Remote Similarity	NPC488937

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC136464 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6427
0.1-0.2	2647
0.2-0.3	56
0.3-0.4	5
0.4-0.5	10
0.5-0.6	4
0.6-0.7	1
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
0.625	Remote Similarity	NPD7507	Pre-clinical
0.5922	Remote Similarity	NPD8033	Approved
0.5714	Remote Similarity	NPD7319	Approved
0.5588	Remote Similarity	NPD8294	Phase 4
0.5138	Remote Similarity	NPD8377	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