NPASS Compound

Natural Product: NPC210037

Natural Product ID	NPC210037
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Triptocallic Acid D
IUPAC Name	(2S,4S,4aR,6aR,6aS,6bR,8aR,10R,12aR,14bS)-4,10-dihydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2-carboxylic acid
Synonyms	Triptocallic Acid D
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL520845
PubChem CID	44575705
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 82 86 0 0 0 0 0 0 0 0999 V2000 -3.9972 -0.2883 -2.9063 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3370 0.0196 -1.5987 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2656 -1.2486 -0.7839 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6377 -0.9956 0.6624 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1611 -0.8158 0.7533 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8833 0.1501 1.2488 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8964 0.7994 0.3132 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5431 1.1473 -1.0070 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5333 2.2921 -0.6501 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5804 1.6514 -2.0201 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1708 1.8319 -1.5533 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6503 0.6191 -0.8737 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5879 0.2034 0.2066 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1449 -0.7111 1.0529 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2042 -1.3531 0.9804 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1758 -0.5286 0.1946 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6859 0.8276 -0.1877 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5161 1.7613 0.9931 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6185 1.4899 -1.1415 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0057 1.5832 -0.5480 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4541 0.1888 -0.2095 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5893 -0.5285 0.7814 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6787 -0.1242 2.1924 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9988 -2.0105 0.7045 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4568 -2.2121 0.5762 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3225 -1.0582 0.9282 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9167 0.1119 0.0451 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6542 -0.1361 -1.2858 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5410 1.3419 0.6144 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6497 -1.4204 0.5923 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5555 -0.4979 -1.8725 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3391 -2.2246 1.4303 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8574 -3.2649 0.8972 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5778 -2.3022 2.8097 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7834 -0.4565 -3.4873 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4137 0.3575 -1.6545 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2806 -1.7440 -0.8644 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0190 -1.9495 -1.1940 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5808 -0.6207 -0.2662 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3334 0.0326 1.4487 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6660 -1.6910 1.1570 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4337 -0.0060 2.2295 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6812 0.9407 1.4515 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7198 1.8263 0.7946 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5613 2.9679 -1.5394 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5481 1.8970 -0.5219 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1598 2.8758 0.1901 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6598 1.0872 -2.9989 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9089 2.6886 -2.3451 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1038 2.7709 -1.0140 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5496 1.9726 -2.4876 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7926 -1.0124 1.8474 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5258 -1.5196 2.0331 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0501 -2.3735 0.5758 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3259 -1.0898 -0.7679 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1317 2.7383 0.5830 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5071 2.0431 1.4100 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0999 1.3751 1.8000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2573 2.5493 -1.2928 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7084 1.0433 -2.1275 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6695 1.9084 -1.4037 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1308 2.3257 0.2251 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2677 -0.3891 -1.1730 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1302 -0.9277 2.8538 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2615 0.7732 2.4232 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6738 0.0321 2.6899 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6612 -2.4867 1.6715 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4775 -2.5444 -0.0892 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6929 -2.4844 -0.4949 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7586 -3.1292 1.1524 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3577 -0.7908 1.9880 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6694 -0.5222 -1.1104 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6986 0.8511 -1.8137 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0102 -0.8160 -1.8640 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4031 1.0748 1.2957 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8986 2.0019 1.1813 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0309 1.9815 -0.1791 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6924 -2.2588 0.1037 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3119 -0.3735 -2.7036 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4114 -0.4941 -2.4295 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7888 -1.5015 -1.4673 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7554 -3.2316 3.2078 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 6 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 1 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 17 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 0 27 29 1 0 26 30 1 0 12 31 1 6 4 32 1 0 32 33 2 0 32 34 1 0 8 2 1 0 17 12 1 0 27 21 1 0 13 7 1 0 22 16 1 0 1 35 1 0 2 36 1 6 3 37 1 0 3 38 1 0 5 39 1 0 5 40 1 0 5 41 1 0 6 42 1 0 6 43 1 0 7 44 1 1 9 45 1 0 9 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 11 50 1 0 11 51 1 0 14 52 1 0 15 53 1 0 15 54 1 0 16 55 1 6 18 56 1 0 18 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 20 61 1 0 20 62 1 0 21 63 1 6 23 64 1 0 23 65 1 0 23 66 1 0 24 67 1 0 24 68 1 0 25 69 1 0 25 70 1 0 26 71 1 1 28 72 1 0 28 73 1 0 28 74 1 0 29 75 1 0 29 76 1 0 29 77 1 0 30 78 1 0 31 79 1 0 31 80 1 0 31 81 1 0 34 82 1 0 M END

Standard InCHIKey	JTBGJQZJEYVBJZ-SXKKXCELSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-25(2)20-10-13-30(7)21(28(20,5)12-11-22(25)31)9-8-18-19-16-26(3,24(33)34)17-23(32)27(19,4)14-15-29(18,30)6/h8,19-23,31-32H,9-17H2,1-7H3,(H,33,34)/t19-,20-,21+,22+,23-,26-,27+,28-,29+,30+/m0/s1
SMILES	O[C@H]1C[C@](C)(C[C@@H]2[C@@]1(C)CC[C@@]1(C2=CC[C@H]2[C@@]1(C)CC[C@@H]1[C@]2(C)CC[C@H](C1(C)C)O)C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	514.542 ? Van der Waals volume.
Dense:	0.918	LogP:	3.282 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.073 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.884 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.397	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.865	Fsp³:	0.9
MCE-18:	108.07 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.815	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.022 ? 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:	0.406	Promiscuous compounds:	0.083

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.139	MDCK Permeability:	-4.851
Pgp-inhibitor:	0.0	Pgp-substrate:	0.243
PAMPA:	0.999 ? 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%):	0.902	30% Bioavailability (F30%):	0.102
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.782	MRP1:	0.991
Plasma Protein Binding (PPB):	83.658%	Volume Distribution (VD):	-0.328
Fu:	13.114% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	0.141	BCRP inhibitor:	0.08
BSEP inhibitor:	0.315

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.986
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.933
HLM stability:	0.0 ? 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):

4.281

Half-life (T1/2):

1.476

ADMET: Toxicity

hERG Blockers:	0.109	hERG Blockers (10um):	0.152
Human Hepatotoxicity (H-HT):	0.662	Drug-induced Liver Injury (DILI):	0.543
AMES Toxicity:	0.34	Rat Oral Acute Toxicity:	0.777
Maximum Recommended Daily Dose:	0.852	Skin Sensitization:	0.995
Carcinogencity:	0.953	Eye Corrosion:	0.004
Eye Irritation:	0.245	Respiratory Toxicity:	0.985
Drug-induced Neurotoxicity:	0.183	Ototoxicity:	0.642
Hematotoxicity:	0.532	Drug-induced Nephrotoxicity:	0.787
Genotoxicity:	0.872	RPMI-8226 Immunitoxicity:	0.055
A549 Cytotoxicity:	0.667	Hek293 Cytotoxicity:	0.53
BCF:	1.035 ? 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:	3.68 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.333 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.639 ? 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
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(90)85349-K]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/S0040-4039(99)00339-1]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1186/1471-2202-6-1]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579865]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[10716597]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10746886]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10757718]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	Kunming, Yunnan, China	n.a.	PMID[10757718]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374948]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11561442]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12579877]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1375626]
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	bark	Leticia, Colombia	n.a.	PMID[15568791]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[16864458]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[16989518]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17250858]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17265278]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18554602]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[18996177]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	root	n.a.	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21514608]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	dried roots	purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China)	n.a.	PMID[22148431]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22256754]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[22256754]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[23252270]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[23268606]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23852638]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24549173]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24963543]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25237706]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2534610]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[2534610]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[2816380]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29355322]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31556299]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Europe PMC[535601]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7102323]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7304185]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8328267]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699928]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8722541]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[Phytochemistry, 2000, 53, 715-722.]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	Kunming, Yunnan, China	n.a.	Database[Title]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	n.a.	n.a.	Database[Title]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	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
Activity	6

Activity Type	# Activity
Cell line	6

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
NPT927	Cell line	PBMC	Homo sapiens	Activity	=	793.2	pg/ml	PMID[15568791]
NPT927	Cell line	PBMC	Homo sapiens	Activity	<	7.8	pg/ml	PMID[15568791]

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 NPC210037 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	21776
0.1-0.2	23477
0.2-0.3	3387
0.3-0.4	869
0.4-0.5	243
0.5-0.6	65
0.6-0.7	24
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC7260
1.0	High Similarity	NPC120968
1.0	High Similarity	NPC227467
1.0	High Similarity	NPC273621
0.7778	Intermediate Similarity	NPC171203
0.7778	Intermediate Similarity	NPC307426
0.7778	Intermediate Similarity	NPC98442
0.7778	Intermediate Similarity	NPC242468
0.746	Intermediate Similarity	NPC477872
0.7424	Intermediate Similarity	NPC193750
0.6667	Remote Similarity	NPC263393
0.6377	Remote Similarity	NPC18872
0.6377	Remote Similarity	NPC290614
0.6324	Remote Similarity	NPC480946
0.6324	Remote Similarity	NPC187722
0.6324	Remote Similarity	NPC130577
0.6324	Remote Similarity	NPC142415
0.6324	Remote Similarity	NPC102683
0.6232	Remote Similarity	NPC182797
0.6232	Remote Similarity	NPC51700
0.6232	Remote Similarity	NPC88716
0.6232	Remote Similarity	NPC68160
0.6232	Remote Similarity	NPC52169
0.6232	Remote Similarity	NPC488562
0.6232	Remote Similarity	NPC606443
0.619	Remote Similarity	NPC290598
0.619	Remote Similarity	NPC30590
0.6154	Remote Similarity	NPC34177
0.6087	Remote Similarity	NPC610937
0.6061	Remote Similarity	NPC235341
0.6056	Remote Similarity	NPC202728
0.6056	Remote Similarity	NPC158059
0.6056	Remote Similarity	NPC293564
0.6	Remote Similarity	NPC112866
0.5909	Remote Similarity	NPC101475
0.5833	Remote Similarity	NPC228784
0.5833	Remote Similarity	NPC155120
0.5833	Remote Similarity	NPC324341
0.5833	Remote Similarity	NPC288833
0.5833	Remote Similarity	NPC601810
0.5797	Remote Similarity	NPC246708
0.5753	Remote Similarity	NPC474525
0.5692	Remote Similarity	NPC27765
0.5692	Remote Similarity	NPC122418
0.5692	Remote Similarity	NPC491014
0.5634	Remote Similarity	NPC274330
0.5634	Remote Similarity	NPC198664
0.5541	Remote Similarity	NPC4036
0.5541	Remote Similarity	NPC65120
0.5541	Remote Similarity	NPC145067
0.5541	Remote Similarity	NPC233455
0.5541	Remote Similarity	NPC158030
0.5507	Remote Similarity	NPC230295
0.5507	Remote Similarity	NPC98386
0.5467	Remote Similarity	NPC46441
0.5467	Remote Similarity	NPC474529
0.5441	Remote Similarity	NPC311078
0.5405	Remote Similarity	NPC49776
0.5405	Remote Similarity	NPC63118
0.5405	Remote Similarity	NPC474436
0.5405	Remote Similarity	NPC29765
0.5375	Remote Similarity	NPC603645
0.5362	Remote Similarity	NPC253807
0.5362	Remote Similarity	NPC158662
0.5342	Remote Similarity	NPC270768
0.5342	Remote Similarity	NPC59263
0.5342	Remote Similarity	NPC263272
0.5342	Remote Similarity	NPC210106
0.5342	Remote Similarity	NPC229281
0.5342	Remote Similarity	NPC121798
0.5342	Remote Similarity	NPC234346
0.5342	Remote Similarity	NPC195019
0.5333	Remote Similarity	NPC474964
0.5286	Remote Similarity	NPC159168
0.5286	Remote Similarity	NPC95594
0.5278	Remote Similarity	NPC477579
0.527	Remote Similarity	NPC472240
0.527	Remote Similarity	NPC61543
0.527	Remote Similarity	NPC293048
0.527	Remote Similarity	NPC225585
0.527	Remote Similarity	NPC262858
0.5224	Remote Similarity	NPC120098
0.5217	Remote Similarity	NPC196753
0.52	Remote Similarity	NPC164349
0.52	Remote Similarity	NPC136697
0.52	Remote Similarity	NPC298554
0.5143	Remote Similarity	NPC40394
0.5139	Remote Similarity	NPC40552
0.5135	Remote Similarity	NPC142361
0.5135	Remote Similarity	NPC474684
0.5135	Remote Similarity	NPC488519
0.5132	Remote Similarity	NPC191412
0.5132	Remote Similarity	NPC114159
0.5132	Remote Similarity	NPC6818
0.507	Remote Similarity	NPC470588
0.5067	Remote Similarity	NPC480720
0.5065	Remote Similarity	NPC476064
0.5065	Remote Similarity	NPC127689
0.5065	Remote Similarity	NPC130520

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC210037 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6333
0.1-0.2	2745
0.2-0.3	65
0.3-0.4	4
0.4-0.5	1
0.5-0.6	2
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
0.5541	Remote Similarity	NPD7515	Phase 2
0.5135	Remote Similarity	NPD7645	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