NPASS Compound

Natural Product: NPC18872

Natural Product ID	NPC18872
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Tripterygic Acid A
IUPAC Name	(1R,2R,4S,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-4,10-dihydroxy-1,4a,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL461696
PubChem CID	21672627
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 -3.9811 -1.7769 -1.9859 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7062 -0.3764 -1.3933 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0522 0.2816 -1.3813 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2189 1.4742 -0.5321 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2153 1.6509 0.5540 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6237 0.3342 1.0300 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8553 -0.4382 1.5584 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7571 0.5983 2.2038 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4615 -0.1746 2.2270 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6931 0.1282 0.9783 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3850 1.5681 0.8920 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5539 -0.4050 -0.1557 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9740 -0.8574 -1.2525 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4799 -0.9164 -1.5256 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2225 -0.3418 -0.4067 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7321 -0.5068 -0.4851 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0989 -1.9165 -0.2443 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1811 -0.0952 -1.8634 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6575 -0.1725 -2.0061 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4734 0.2816 -0.8431 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7599 0.7443 0.3633 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4922 0.1095 1.5605 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0434 2.2472 0.5377 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2948 0.4810 0.4733 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8968 0.0544 1.8514 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4929 -0.3033 2.0830 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6424 -0.6802 0.9109 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1363 -2.0970 1.0626 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4810 -0.6787 -0.5439 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0320 -0.4964 -0.0600 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3004 2.5837 0.1537 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3259 0.6833 -2.8107 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5126 1.8878 -3.1181 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3822 -0.2516 -3.8345 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0659 -2.0349 -1.9264 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4835 -2.5708 -1.3722 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7214 -1.8337 -3.0492 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0754 0.2146 -2.1192 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8628 -0.4810 -1.1711 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2712 1.4518 -0.1138 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2382 2.4187 -1.1579 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7823 2.0357 1.4570 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9048 -0.3983 2.6652 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7937 -0.0444 1.1800 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7474 -1.5112 1.2992 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2778 0.2661 3.1713 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6459 1.6879 2.3768 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9204 0.0698 3.1696 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7974 -1.2598 2.2540 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9796 2.2358 1.5486 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5404 1.8957 -0.1750 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6671 1.8333 1.1383 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6431 -1.2242 -2.0464 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8014 -1.9911 -1.7160 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6783 -0.4370 -2.5180 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1219 0.7899 -0.5416 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5230 -2.5678 -0.9239 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1667 -2.1521 -0.5575 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0831 -2.2231 0.8215 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7691 0.8976 -2.1713 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7468 -0.8286 -2.6036 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9353 -1.2478 -2.2150 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9171 0.3442 -2.9776 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1137 1.1268 -1.2565 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5297 -0.9736 1.4964 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5591 0.4657 1.4374 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1627 0.5348 2.5128 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1802 2.7626 1.0022 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9624 2.4344 1.0831 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1706 2.7210 -0.4758 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7960 1.4541 0.2937 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6214 -0.7520 2.1758 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1592 0.9154 2.5364 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4937 -1.1689 2.8138 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9572 0.5012 2.6485 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9108 -2.2443 0.7377 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8139 -2.8778 0.7052 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0900 -2.2662 2.1835 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3274 -0.2786 -0.2970 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2541 -1.5789 0.2579 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0726 3.2077 0.8867 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4130 0.0577 -4.8174 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 1 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 6 10 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 20 29 1 0 12 30 1 0 5 31 1 0 3 32 1 0 32 33 2 0 32 34 1 0 30 2 1 0 30 6 1 0 27 10 1 0 27 15 1 0 24 16 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 6 3 39 1 1 4 40 1 0 4 41 1 0 5 42 1 1 7 43 1 0 7 44 1 0 7 45 1 0 8 46 1 0 8 47 1 0 9 48 1 0 9 49 1 0 11 50 1 0 11 51 1 0 11 52 1 0 13 53 1 0 14 54 1 0 14 55 1 0 15 56 1 6 17 57 1 0 17 58 1 0 17 59 1 0 18 60 1 0 18 61 1 0 19 62 1 0 19 63 1 0 20 64 1 6 22 65 1 0 22 66 1 0 22 67 1 0 23 68 1 0 23 69 1 0 23 70 1 0 24 71 1 6 25 72 1 0 25 73 1 0 26 74 1 0 26 75 1 0 28 76 1 0 28 77 1 0 28 78 1 0 29 79 1 0 30 80 1 1 31 81 1 0 34 82 1 0 M END

Standard InCHIKey	IWVWTVWLRSUYNC-YLOASUEESA-N
Standard InCHI	InChI=1S/C30H48O4/c1-17-18(25(33)34)16-23(32)28(5)14-15-29(6)19(24(17)28)8-9-21-27(4)12-11-22(31)26(2,3)20(27)10-13-30(21,29)7/h8,17-18,20-24,31-32H,9-16H2,1-7H3,(H,33,34)/t17-,18+,20-,21+,22-,23-,24-,27-,28-,29+,30+/m0/s1
SMILES	C[C@H]1[C@@H](C[C@@H]([C@]2(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@H]12)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	514.542 ? Van der Waals volume.
Dense:	0.918	LogP:	3.524 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.121 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.542 ? 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:	0.405	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.936	Fsp³:	0.9
MCE-18:	105.368 ? 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:	0.676	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.105 ? 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:	0.327	Promiscuous compounds:	0.055

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.614	MDCK Permeability:	-5.138
Pgp-inhibitor:	0.0	Pgp-substrate:	0.219
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%):	0.684	30% Bioavailability (F30%):	0.062
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.167	MRP1:	0.966
Plasma Protein Binding (PPB):	93.662%	Volume Distribution (VD):	-0.485
Fu:	6.24% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.816	BCRP inhibitor:	0.056
BSEP inhibitor:	0.447

ADMET: Metabolism

CYP1A2-inhibitor:	0.022	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.989	CYP2C19-substrate:	0.006
CYP2C9-inhibitor:	0.006	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.011	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.032	CYP3A4-substrate:	0.024
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.05
HLM stability:	0.557 ? 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):

3.924

Half-life (T1/2):

1.258

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.016
Human Hepatotoxicity (H-HT):	0.541	Drug-induced Liver Injury (DILI):	0.395
AMES Toxicity:	0.179	Rat Oral Acute Toxicity:	0.229
Maximum Recommended Daily Dose:	0.273	Skin Sensitization:	0.858
Carcinogencity:	0.84	Eye Corrosion:	0.015
Eye Irritation:	0.708	Respiratory Toxicity:	0.538
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.772
Hematotoxicity:	0.632	Drug-induced Nephrotoxicity:	0.917
Genotoxicity:	0.472	RPMI-8226 Immunitoxicity:	0.026
A549 Cytotoxicity:	0.083	Hek293 Cytotoxicity:	0.097
BCF:	0.628 ? 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:	3.485 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.213 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.494 ? 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]
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]
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10757717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	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]
NPO2353	Bituminaria bituminosa	Species	Fabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[12943781]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12951446]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1375626]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	stems	Thailand	n.a.	PMID[14510595]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738381]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	Argentine	n.a.	PMID[14738381]
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]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21905650]
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]
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]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24697288]
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]
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]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32998509]
NPO16758	Satureja cuneifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36031812]
NPO16758	Satureja cuneifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36938717]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37533365]
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]
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]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[9599285]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16428	Millettia conraui	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2353	Bituminaria bituminosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14869	Ormosia panamensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11599	Elaeagnus commutata	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15393	Eucalyptus flocktoniae	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13548	Chrozophora obliqua	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26017	Dalbergia stipulacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13375	Palafoxia rosea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16516	Centaurea seridis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9780	Merremia umbellata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15858	Phoebe formosana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16175	Trichia floriformis	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12555	Aspergillus quadrilineatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16678	Flindersia brayleyana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14869	Ormosia panamensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13859	Senecio flavus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13710	Lyophyllum shimeji	Species	Lyophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3391	Jungermannia obovata	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16428	Millettia conraui	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13375	Palafoxia rosea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24732	Cereus weberi	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15138	Rheum webbianum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4267	Ceratocystis clavigera	Species	Ceratocystidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11194	Bombus hortorum	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5552	Solanum sisymbriifolium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16175	Trichia floriformis	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13230	Pedicularis condensata	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11599	Elaeagnus commutata	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15272	Mascarenhasia arborescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5078	Turraeanthus mannii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4935	Dinemasporium strigosum	Species	Chaetosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15755	Thymbra spicata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5269	Coleus garckeanus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11881	Adenopeltis colliguaya	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14869	Ormosia panamensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2353	Bituminaria bituminosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16678	Flindersia brayleyana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12680	Perityle vaseyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15393	Eucalyptus flocktoniae	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26017	Dalbergia stipulacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14218	Spodoptera littoralis	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16516	Centaurea seridis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16758	Satureja cuneifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13548	Chrozophora obliqua	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8499	Osmerus mordax	Species	Osmeridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14034	Salvia coulteri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9780	Merremia umbellata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15858	Phoebe formosana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15015	Meconopsis napaulensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12555	Aspergillus quadrilineatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23289	Heracleum sphondylium	Species	Apiaceae	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
IC50	1
Inhibition	1

Activity Type	# Activity
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual protein	Aldose reductase	Rattus norvegicus	IC50	>	100000.0	nM	PMID[14510595]
NPT68	Individual protein	Aldose reductase	Rattus norvegicus	Inhibition	=	27.0	%	PMID[14510595]

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 NPC18872 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	22351
0.1-0.2	23423
0.2-0.3	3118
0.3-0.4	751
0.4-0.5	158
0.5-0.6	41
0.6-0.7	9
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC290614
0.7778	Intermediate Similarity	NPC610937
0.7463	Intermediate Similarity	NPC105189
0.6377	Remote Similarity	NPC7260
0.6377	Remote Similarity	NPC210037
0.6377	Remote Similarity	NPC120968
0.6377	Remote Similarity	NPC227467
0.6377	Remote Similarity	NPC273621
0.6377	Remote Similarity	NPC112866
0.6094	Remote Similarity	NPC27765
0.6094	Remote Similarity	NPC122418
0.6094	Remote Similarity	NPC491014
0.5915	Remote Similarity	NPC171203
0.5915	Remote Similarity	NPC307426
0.5915	Remote Similarity	NPC98442
0.5915	Remote Similarity	NPC242468
0.5857	Remote Similarity	NPC477872
0.5775	Remote Similarity	NPC480946
0.5775	Remote Similarity	NPC187722
0.5775	Remote Similarity	NPC130577
0.5775	Remote Similarity	NPC142415
0.5775	Remote Similarity	NPC102683
0.5694	Remote Similarity	NPC182797
0.5694	Remote Similarity	NPC51700
0.5694	Remote Similarity	NPC88716
0.5694	Remote Similarity	NPC68160
0.5694	Remote Similarity	NPC52169
0.5694	Remote Similarity	NPC488562
0.5694	Remote Similarity	NPC606443
0.5652	Remote Similarity	NPC95594
0.5634	Remote Similarity	NPC477579
0.5606	Remote Similarity	NPC290598
0.5606	Remote Similarity	NPC30590
0.5588	Remote Similarity	NPC132478
0.5588	Remote Similarity	NPC34177
0.5541	Remote Similarity	NPC202728
0.5541	Remote Similarity	NPC158059
0.5541	Remote Similarity	NPC293564
0.5507	Remote Similarity	NPC235341
0.5507	Remote Similarity	NPC40394
0.5493	Remote Similarity	NPC40552
0.5362	Remote Similarity	NPC101475
0.5342	Remote Similarity	NPC274330
0.5342	Remote Similarity	NPC198664
0.5333	Remote Similarity	NPC228784
0.5333	Remote Similarity	NPC324341
0.5333	Remote Similarity	NPC601810
0.5278	Remote Similarity	NPC246708
0.527	Remote Similarity	NPC142361
0.527	Remote Similarity	NPC474684
0.5147	Remote Similarity	NPC120098
0.5067	Remote Similarity	NPC195019
0.5065	Remote Similarity	NPC263393

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC18872 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6330
0.1-0.2	2759
0.2-0.3	58
0.3-0.4	1
0.4-0.5	2
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