NPASS Compound

Natural Product: NPC143231

Natural Product ID	NPC143231
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LDOSJSVSRRNOHL-PGSCOJJMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	70697805
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

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 119125 0 0 0 0 0 0 0 0999 V2000 10.5243 -2.0551 -1.0422 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7219 -1.3326 0.0001 C 0 0 1 0 0 0 0 0 0 0 0 0 10.5816 -0.6527 1.0432 C 0 0 2 0 0 0 0 0 0 0 0 0 10.5026 0.8538 0.8984 C 0 0 2 0 0 0 0 0 0 0 0 0 9.0443 1.2441 1.1733 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2024 0.3885 0.2824 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9679 -0.3596 -0.6237 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3408 -0.4716 0.9710 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0382 -0.2347 0.6133 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0904 0.0545 1.7244 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7047 1.5156 1.6640 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0192 -0.7835 1.8536 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2539 -1.0203 0.7552 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0559 -0.9164 -0.5589 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4542 -1.4209 -0.1733 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2754 -2.4501 0.7284 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8814 -3.6319 0.3717 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1944 -0.1777 0.6122 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9590 -0.8130 0.4324 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0057 -0.6413 1.5125 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3689 -0.2581 1.0948 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4041 0.8617 0.0672 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8103 2.0790 0.6637 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6353 0.3492 -1.1400 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0541 0.6842 -2.3128 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2107 1.5187 -2.7099 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9499 2.0364 -1.4904 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7966 0.9690 -0.4499 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8669 1.0536 0.5717 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1489 0.7487 -0.2310 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4764 1.8961 -1.1214 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2389 2.8770 -0.2024 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4577 1.5994 -2.1966 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2091 2.7517 -3.1781 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6824 2.7659 -3.1720 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2925 2.5810 -1.7209 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3068 3.9143 -1.2099 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3402 0.3657 -2.9335 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3723 -0.1225 -3.4475 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5934 -0.4650 -3.1084 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7804 1.7933 -1.7625 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1437 0.3908 0.6996 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6158 -0.9024 0.8353 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1317 -1.7860 0.0901 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6438 -1.3138 1.7922 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0504 -2.5657 1.8769 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0561 -3.0370 2.7950 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6973 -2.2156 3.6759 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6666 -2.6867 4.5652 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9732 -4.0108 4.5423 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3498 -4.8881 3.6648 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4073 -4.3723 2.8155 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0961 3.0966 -1.0610 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5260 -0.5448 -0.9354 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8487 1.2928 -0.3638 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8713 2.2340 -0.2717 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8967 -1.0536 0.8671 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8480 -2.8553 -1.4567 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4638 -2.4570 -0.6621 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6722 -1.3562 -1.9117 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0451 -2.0368 0.5533 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2472 -0.8847 2.0755 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1031 1.3375 1.6697 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8033 1.2037 2.2348 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9894 2.3358 0.8875 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6007 1.0774 -0.3805 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0135 0.6033 -0.1449 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6855 -0.0599 2.6796 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 2.1171 2.2309 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7960 1.8355 0.5874 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6498 1.6574 1.9342 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9513 -2.1128 0.7344 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6233 -1.5457 -1.3422 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1109 0.1078 -0.9259 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0501 -1.6700 -1.0488 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9867 -3.5349 0.2583 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3990 -4.1244 -0.4953 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7515 -4.3317 1.2417 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2669 -1.9287 0.4592 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1574 -1.5738 2.1410 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4412 0.0673 2.2702 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9130 -1.1516 0.7307 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8975 0.1593 1.9969 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1313 1.8028 1.5243 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0922 2.6223 -0.0198 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5461 2.7612 1.1387 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4647 0.2924 -3.1714 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8403 0.8485 -3.3426 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8153 2.3763 -3.2874 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9836 -0.0039 -1.0112 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8068 0.2544 1.3460 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9717 2.0575 0.9727 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8805 -0.1900 -0.7786 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7436 2.9645 0.7617 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3877 3.8464 -0.7040 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2270 2.3954 -0.0170 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5816 2.5249 -4.1914 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6456 3.6900 -2.8406 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3391 2.0070 -3.8585 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3643 3.7552 -3.5652 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0518 4.5655 -1.8847 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3758 -1.5337 -3.1744 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1165 -0.1133 -4.0032 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2814 -0.3140 -2.2532 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3842 1.7557 -2.5487 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0895 -0.5864 2.4513 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5685 -3.2749 1.1842 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4939 -1.1612 3.7371 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1749 -2.0418 5.2622 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7132 -4.4241 5.2066 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5939 -5.9371 3.6480 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8915 -5.0373 2.1048 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0936 3.7337 -1.8368 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3614 -1.5337 -1.4743 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3626 -0.0917 -1.5506 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1164 2.5597 -1.3206 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5709 3.1155 0.3177 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8054 1.7856 0.1381 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3568 -1.0823 1.7448 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 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 13 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 2 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 1 31 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 1 33 38 1 0 38 39 2 0 38 40 1 0 33 41 1 1 30 42 1 0 42 43 1 0 43 44 2 0 43 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 27 53 1 1 24 54 1 0 4 55 1 0 55 56 1 0 3 57 1 0 7 2 1 0 15 9 1 0 54 19 1 0 28 22 1 0 36 31 1 0 52 47 1 0 36 27 1 0 1 58 1 0 1 59 1 0 1 60 1 0 2 61 1 1 3 62 1 1 4 63 1 1 5 64 1 0 5 65 1 0 6 66 1 6 9 67 1 6 10 68 1 1 11 69 1 0 11 70 1 0 11 71 1 0 13 72 1 1 14 73 1 0 14 74 1 0 15 75 1 6 17 76 1 0 17 77 1 0 17 78 1 0 19 79 1 6 20 80 1 0 20 81 1 0 21 82 1 0 21 83 1 0 23 84 1 0 23 85 1 0 23 86 1 0 25 87 1 0 26 88 1 0 26 89 1 0 28 90 1 6 29 91 1 0 29 92 1 0 30 93 1 6 32 94 1 0 32 95 1 0 32 96 1 0 34 97 1 0 34 98 1 0 35 99 1 0 35100 1 0 37101 1 0 40102 1 0 40103 1 0 40104 1 0 41105 1 0 45106 1 0 46107 1 0 48108 1 0 49109 1 0 50110 1 0 51111 1 0 52112 1 0 53113 1 0 54114 1 0 54115 1 0 56116 1 0 56117 1 0 56118 1 0 57119 1 0 M END

Standard InCHIKey	LDOSJSVSRRNOHL-PGSCOJJMSA-N
Standard InCHI	InChI=1S/C44H62O13/c1-25-38(47)31(51-6)22-37(53-25)57-39-26(2)54-36(23-32(39)52-7)55-30-16-17-40(4)29(21-30)15-18-43(49)33(40)24-34(56-35(46)14-13-28-11-9-8-10-12-28)41(5)42(48,27(3)45)19-20-44(41,43)50/h8-15,25-26,30-34,36-39,47-50H,16-24H2,1-7H3/b14-13+/t25-,26+,30-,31-,32-,33+,34+,36-,37-,38+,39+,40-,41+,42+,43-,44+/m0/s1
SMILES	C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@@H]1[C@@H](C)O[C@H](C[C@@H]1OC)O[C@H]1CC[C@@]2(C)C(=CC[C@@]3([C@@H]2C[C@H]([C@]2(C)[C@@](CC[C@]32O)(C(=O)C)O)OC(=O)/C=C/c2ccccc2)O)C1)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	798.42	Volume:	805.502 ? Van der Waals volume.
Dense:	0.991	LogP:	3.384 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.441 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.062 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	41.0
TPSA:	179.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	4.0	Rings:	7.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.151	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.885	Fsp³:	0.727
MCE-18:	186.553 ? 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:	0.953	Fluc inhibitor:	0.45 ? 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:	0.314 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.13	Promiscuous compounds:	0.438

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.478	MDCK Permeability:	-5.201
Pgp-inhibitor:	0.024	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):	0.0
20% Bioavailability (F20%):	0.474	30% Bioavailability (F30%):	0.33
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.702
Plasma Protein Binding (PPB):	91.507%	Volume Distribution (VD):	0.381
Fu:	7.563% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.892	BCRP inhibitor:	0.021
BSEP inhibitor:	0.983

ADMET: Metabolism

CYP1A2-inhibitor:	0.011	CYP1A2-substrate:	0.016
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.108
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.884	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.568 ? 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):

5.389

Half-life (T1/2):

3.609

ADMET: Toxicity

hERG Blockers:	0.141	hERG Blockers (10um):	0.345
Human Hepatotoxicity (H-HT):	0.566	Drug-induced Liver Injury (DILI):	0.932
AMES Toxicity:	0.944	Rat Oral Acute Toxicity:	0.697
Maximum Recommended Daily Dose:	0.971	Skin Sensitization:	1.0
Carcinogencity:	0.559	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.428
Drug-induced Neurotoxicity:	0.101	Ototoxicity:	0.915
Hematotoxicity:	0.427	Drug-induced Nephrotoxicity:	0.925
Genotoxicity:	0.934	RPMI-8226 Immunitoxicity:	0.368
A549 Cytotoxicity:	0.946	Hek293 Cytotoxicity:	0.928
BCF:	0.69 ? 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:	3.639 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.502 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.737 ? 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
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	root	n.a.	PMID[18401845]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	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 NPC143231 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	11186
0.1-0.2	35202
0.2-0.3	3258
0.3-0.4	151
0.4-0.5	16
0.5-0.6	10
0.6-0.7	16
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC165234
1.0	High Similarity	NPC481659
1.0	High Similarity	NPC271687
0.8878	High Similarity	NPC475536
0.8431	Intermediate Similarity	NPC481654
0.7961	Intermediate Similarity	NPC474564
0.7957	Intermediate Similarity	NPC481657
0.785	Intermediate Similarity	NPC473641
0.785	Intermediate Similarity	NPC475300
0.7835	Intermediate Similarity	NPC481658
0.7835	Intermediate Similarity	NPC79250
0.7835	Intermediate Similarity	NPC290746
0.7706	Intermediate Similarity	NPC475437
0.7706	Intermediate Similarity	NPC475464
0.7679	Intermediate Similarity	NPC481660
0.7477	Intermediate Similarity	NPC475567
0.7407	Intermediate Similarity	NPC475613
0.7368	Intermediate Similarity	NPC473797
0.7071	Intermediate Similarity	NPC473519
0.7054	Intermediate Similarity	NPC70236
0.693	Remote Similarity	NPC476092
0.6897	Remote Similarity	NPC481648
0.6667	Remote Similarity	NPC473805
0.6667	Remote Similarity	NPC475175
0.6639	Remote Similarity	NPC475447
0.6636	Remote Similarity	NPC481662
0.6465	Remote Similarity	NPC481656
0.6449	Remote Similarity	NPC481661
0.6449	Remote Similarity	NPC481655
0.6393	Remote Similarity	NPC475531
0.6393	Remote Similarity	NPC475198
0.6349	Remote Similarity	NPC481650
0.6195	Remote Similarity	NPC473468
0.6147	Remote Similarity	NPC102015
0.6077	Remote Similarity	NPC476090
0.605	Remote Similarity	NPC473557
0.5833	Remote Similarity	NPC475218
0.582	Remote Similarity	NPC478508
0.582	Remote Similarity	NPC478510
0.582	Remote Similarity	NPC478509
0.5588	Remote Similarity	NPC481647
0.5455	Remote Similarity	NPC481649
0.5439	Remote Similarity	NPC475358
0.5439	Remote Similarity	NPC473566
0.5328	Remote Similarity	NPC478507
0.5043	Remote Similarity	NPC305378

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC143231 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4577
0.1-0.2	4509
0.2-0.3	59
0.3-0.4	5
0.4-0.5	0
0.5-0.6	0
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
		NPD

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