NPASS Compound

Natural Product: NPC475631

Natural Product ID	NPC475631
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DPTIBNOQWFLHCG-PDVUZMAKSA-N
IUPAC Name	n.a.
Synonyms	Cangorinine E-1; Cangoronine E-1; Congorinine E-1
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL509754
PubChem CID	44593670
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids 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 111116 0 0 0 0 0 0 0 0999 V2000 4.9409 2.9699 -1.1885 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0885 1.7315 -0.8508 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0656 0.9157 -2.1177 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1348 -0.2576 -2.0331 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4420 -1.4419 -2.1351 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8475 0.0213 -1.8309 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6613 -0.5880 -1.6951 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4366 -1.7655 -0.8457 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0808 -2.0192 -0.7963 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8910 -0.9528 -0.1554 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2581 -1.2214 1.2972 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6184 0.0430 1.9494 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6631 1.2118 1.7830 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7342 1.5187 0.3162 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0291 0.2718 -0.1263 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3366 0.5625 -1.4054 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1655 0.9210 -2.5835 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3918 1.7630 -1.1389 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0713 0.0047 0.8603 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1982 0.7889 1.9473 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7569 1.9457 1.9796 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0460 1.7445 1.4975 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0187 0.9002 1.9079 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6463 0.1899 2.8946 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3508 0.6679 1.4511 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8139 1.0253 0.2415 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1147 0.7435 -0.0789 N 0 0 0 0 0 0 0 0 0 0 0 0 6.9613 0.1337 0.7340 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5289 -0.2495 1.9830 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2236 0.0227 2.3290 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1414 0.1999 3.3184 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2617 2.7182 -0.1199 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9823 3.7455 -0.7077 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2302 3.5291 -0.8501 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4024 4.9928 -1.1444 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0547 5.2032 -0.9857 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5594 6.3769 -1.3814 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1898 7.3738 -1.9534 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5378 7.1922 -2.1248 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1423 6.0004 -1.7194 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2481 0.0996 3.1409 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4873 0.4379 3.5350 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1978 0.7698 2.5784 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9691 0.4266 4.9119 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3620 -2.0824 1.8338 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5772 -3.3776 2.2963 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7542 -3.8141 2.2127 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4776 -4.2111 2.8624 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1634 -0.8821 -0.9228 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7769 -2.1844 -0.8003 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0078 -2.3351 -1.4656 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4990 -1.3763 -2.1072 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7585 -3.6158 -1.4324 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3786 -3.3359 -0.4819 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8214 -4.3223 -1.3178 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9843 -4.0018 -2.5446 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1043 -5.7014 -0.8426 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8643 -2.9319 -1.5906 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6778 -3.8455 -0.9659 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0395 -3.6720 0.2185 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1470 -5.0564 -1.6741 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4141 0.4979 -2.6000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6470 3.8195 -0.5321 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9886 2.6893 -0.9818 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8357 3.1835 -2.2498 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1119 2.0621 -0.5561 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6299 1.5859 -2.9091 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3244 -0.9055 -2.7515 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9060 -1.8511 0.1154 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3057 -1.9686 -1.9142 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2296 -1.8125 1.2737 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4994 0.3924 1.2790 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9483 2.0037 2.4541 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8419 1.5185 0.0947 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6878 1.7333 -3.2214 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1465 1.3623 -2.3277 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2458 0.0853 -3.3424 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0488 1.8791 -1.8747 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3752 2.8681 1.4941 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9182 2.3164 3.0451 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0042 -0.0855 0.4611 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2159 -0.7541 2.6671 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8867 -0.2877 3.3354 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3799 0.8786 4.0704 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2921 -0.7626 3.4872 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1562 0.1596 3.8339 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5424 4.4442 -0.5454 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6149 6.5381 -1.2560 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2466 8.3225 -2.2843 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1235 7.9681 -2.5708 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2050 5.8704 -1.8602 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3287 -0.5840 5.2345 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7917 1.1433 5.1122 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1647 0.6863 5.6512 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7405 -4.5183 3.8975 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3577 -5.1372 2.2732 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4477 -3.6363 2.9055 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9065 -0.1756 -0.6345 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0061 -0.8178 -2.0213 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9457 -3.9324 -2.4795 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2411 -4.3649 -0.8220 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7703 -3.3731 -1.0139 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4515 -6.4506 -1.3387 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8854 -5.7454 0.2340 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1773 -5.9815 -0.9686 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0913 -4.7897 -2.1945 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4330 -5.8702 -0.9543 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3472 -5.3954 -2.3627 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3237 0.3479 -3.7158 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1186 1.3423 -2.4846 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8110 -0.4197 -2.1168 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 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 16 18 1 0 15 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 20 31 1 0 14 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 12 41 1 0 41 42 1 0 42 43 2 0 42 44 1 0 11 45 1 0 45 46 1 0 46 47 2 0 46 48 1 0 10 49 1 0 49 50 1 0 50 51 1 0 51 52 2 0 51 53 1 0 9 54 1 0 54 55 1 0 55 56 2 0 55 57 1 0 8 58 1 0 58 59 1 0 59 60 2 0 59 61 1 0 3 62 1 0 26 2 1 0 16 7 1 0 15 10 1 0 20 13 1 0 30 25 1 0 40 35 1 0 1 63 1 0 1 64 1 0 1 65 1 0 2 66 1 0 3 67 1 0 7 68 1 0 8 69 1 0 9 70 1 0 11 71 1 0 12 72 1 0 13 73 1 0 14 74 1 0 17 75 1 0 17 76 1 0 17 77 1 0 18 78 1 0 21 79 1 0 21 80 1 0 28 81 1 0 29 82 1 0 30 83 1 0 31 84 1 0 31 85 1 0 31 86 1 0 36 87 1 0 37 88 1 0 38 89 1 0 39 90 1 0 40 91 1 0 44 92 1 0 44 93 1 0 44 94 1 0 48 95 1 0 48 96 1 0 48 97 1 0 49 98 1 0 49 99 1 0 53100 1 0 53101 1 0 53102 1 0 57103 1 0 57104 1 0 57105 1 0 61106 1 0 61107 1 0 61108 1 0 62109 1 0 62110 1 0 62111 1 0 M END

Standard InCHIKey	DPTIBNOQWFLHCG-PDVUZMAKSA-N
Standard InCHI	InChI=1S/C43H49NO18/c1-20-21(2)37(50)61-34-32(57-24(5)47)36(59-26(7)49)42(19-54-22(3)45)35(58-25(6)48)31(56-23(4)46)29-33(60-38(51)27-14-11-10-12-15-27)43(42,41(34,9)53)62-40(29,8)18-55-39(52)28-16-13-17-44-30(20)28/h10-17,20-21,29,31-36,53H,18-19H2,1-9H3/t20?,21?,29-,31-,32+,33-,34+,35-,36+,40+,41+,42-,43+/m1/s1
SMILES	CC1C(C(=O)OC2C(C(C3(C(C(C4C(C3(C2(C)O)OC4(COC(=O)C5=C1N=CC=C5)C)OC(=O)C6=CC=CC=C6)OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	867.29	Volume:	833.255 ? Van der Waals volume.
Dense:	1.041	LogP:	1.308 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.698 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.074 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	43.0
TPSA:	252.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.295	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.587	Fsp³:	0.558
MCE-18:	220.896 ? 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:	0.148	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.194 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.017	Promiscuous compounds:	0.016

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.195	MDCK Permeability:	-4.733
Pgp-inhibitor:	0.614	Pgp-substrate:	0.732
PAMPA:	0.984 ? 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%):	0.003	30% Bioavailability (F30%):	0.372
50% Bioavailability (F50%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007	MRP1:	1.0
Plasma Protein Binding (PPB):	62.973%	Volume Distribution (VD):	-0.409
Fu:	35.258% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.065
OATP1B3 inhibitor:	0.754	BCRP inhibitor:	0.0
BSEP inhibitor:	0.993

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:	0.001
CYP3A4-inhibitor:	0.048	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.571 ? 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):

0.087

Half-life (T1/2):

1.64

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.173
Human Hepatotoxicity (H-HT):	0.455	Drug-induced Liver Injury (DILI):	0.994
AMES Toxicity:	0.765	Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.333	Skin Sensitization:	0.995
Carcinogencity:	0.781	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.682	Ototoxicity:	0.897
Hematotoxicity:	0.199	Drug-induced Nephrotoxicity:	0.95
Genotoxicity:	0.946	RPMI-8226 Immunitoxicity:	0.108
A549 Cytotoxicity:	0.016	Hek293 Cytotoxicity:	0.265
BCF:	0.653 ? 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:	3.631 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.844 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.195 ? 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]
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]
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]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1602302]
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[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]
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]
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]
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]
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]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13661	Tripterygium wilfordii	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
IC50	2
EC50	2
Inhibition	7

Activity Type	# Activity
Cell line	8
Organism	3

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
NPT759	Cell line	H9	Homo sapiens	IC50	=	56.8	ug.mL-1	PMID[18443122]
NPT927	Cell line	PBMC	Homo sapiens	Inhibition	=	37.0	%	PMID[19258275]
NPT927	Cell line	PBMC	Homo sapiens	Inhibition	=	43.0	%	PMID[19258276]
NPT927	Cell line	PBMC	Homo sapiens	Inhibition	=	84.0	%	PMID[19258276]
NPT927	Cell line	PBMC	Homo sapiens	Inhibition	=	100.0	%	PMID[19258276]
NPT927	Cell line	PBMC	Homo sapiens	Inhibition	=	99.0	%	PMID[15104488]
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	Inhibition	=	22.3	%	PMID[11141104]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	0.9	ug.mL-1	PMID[21893415]

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 NPC475631 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	22791
0.1-0.2	25736
0.2-0.3	1046
0.3-0.4	193
0.4-0.5	23
0.5-0.6	18
0.6-0.7	17
0.7-0.8	0
0.8-0.85	5
0.85-0.9	3
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.967	High Similarity	NPC475596
0.9247	High Similarity	NPC476110
0.914	High Similarity	NPC87152
0.914	High Similarity	NPC475600
0.9032	High Similarity	NPC475303
0.8878	High Similarity	NPC327769
0.8681	High Similarity	NPC76565
0.8681	High Similarity	NPC601313
0.8438	Intermediate Similarity	NPC475301
0.8367	Intermediate Similarity	NPC30456
0.8367	Intermediate Similarity	NPC488904
0.8061	Intermediate Similarity	NPC328186
0.8	Intermediate Similarity	NPC475644
0.7959	Intermediate Similarity	NPC326930
0.78	Intermediate Similarity	NPC316841
0.7778	Intermediate Similarity	NPC483854
0.7767	Intermediate Similarity	NPC319880
0.7767	Intermediate Similarity	NPC320324
0.7706	Intermediate Similarity	NPC482915
0.7624	Intermediate Similarity	NPC470486
0.7524	Intermediate Similarity	NPC327904
0.7524	Intermediate Similarity	NPC328928
0.7524	Intermediate Similarity	NPC38959
0.7451	Intermediate Similarity	NPC471977
0.7429	Intermediate Similarity	NPC477787
0.7353	Intermediate Similarity	NPC122968
0.7353	Intermediate Similarity	NPC228377
0.729	Intermediate Similarity	NPC483853
0.729	Intermediate Similarity	NPC608314
0.7245	Intermediate Similarity	NPC35208
0.703	Intermediate Similarity	NPC475498
0.7009	Intermediate Similarity	NPC244839
0.7	Intermediate Similarity	NPC475137
0.7	Intermediate Similarity	NPC475426
0.6916	Remote Similarity	NPC473689
0.6916	Remote Similarity	NPC292416
0.69	Remote Similarity	NPC250807
0.69	Remote Similarity	NPC57797
0.6887	Remote Similarity	NPC471190
0.6842	Remote Similarity	NPC483856
0.6697	Remote Similarity	NPC475406
0.6476	Remote Similarity	NPC146824
0.6476	Remote Similarity	NPC473833
0.6355	Remote Similarity	NPC53255
0.6355	Remote Similarity	NPC85879
0.6303	Remote Similarity	NPC483855
0.6154	Remote Similarity	NPC470306
0.6106	Remote Similarity	NPC600583
0.6106	Remote Similarity	NPC601643
0.6036	Remote Similarity	NPC328154
0.6036	Remote Similarity	NPC477788
0.5982	Remote Similarity	NPC13603
0.5965	Remote Similarity	NPC253482
0.5963	Remote Similarity	NPC473506
0.5812	Remote Similarity	NPC471979
0.5804	Remote Similarity	NPC475533
0.569	Remote Similarity	NPC237702
0.569	Remote Similarity	NPC475648
0.5596	Remote Similarity	NPC471016
0.5505	Remote Similarity	NPC473850
0.5431	Remote Similarity	NPC324619
0.5351	Remote Similarity	NPC475362
0.5333	Remote Similarity	NPC170751
0.5214	Remote Similarity	NPC475315
0.521	Remote Similarity	NPC600607
0.521	Remote Similarity	NPC611166
0.5169	Remote Similarity	NPC600224
0.5083	Remote Similarity	NPC483893
0.5042	Remote Similarity	NPC604935

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475631 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4416
0.1-0.2	4694
0.2-0.3	39
0.3-0.4	1
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