NPASS Compound

Natural Product: NPC195647

Natural Product ID	NPC195647
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BGJHHQRHKDDKIR-OKPVOZINSA-N
IUPAC Name	n.a.
Synonyms	Triptogelin C-1
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL521803
PubChem CID	10459206
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

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 73 76 0 0 0 0 0 0 0 0999 V2000 -0.4349 -2.3180 5.1136 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4913 -2.0948 3.6527 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1500 -3.0107 2.8747 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9137 -0.8930 3.1239 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9679 -0.6821 1.7302 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4151 -0.4499 1.3521 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5596 -0.3012 -0.1455 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8394 0.4045 -0.4320 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3393 0.1854 -0.8238 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4280 1.0759 -0.0126 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1060 0.4990 1.3384 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3306 1.4956 2.3368 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7083 1.8405 3.1793 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8580 1.3326 3.1357 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5094 2.8907 4.2429 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9720 2.4802 0.1802 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8992 1.2495 -0.7276 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8411 0.2483 -0.3878 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0501 0.4864 0.2098 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3626 1.6966 0.4807 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0163 -0.5281 0.5656 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2244 -0.2418 1.1631 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1276 -1.2290 1.4938 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8521 -2.5487 1.2360 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6558 -2.8568 0.6417 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7472 -1.8505 0.3105 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7547 1.4129 -2.2178 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2888 0.5625 -2.8470 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6065 0.9004 -2.1189 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6051 0.3418 -2.9186 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4943 1.1864 -3.5709 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4220 2.4369 -3.4612 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5692 0.6241 -4.4273 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2060 -0.8983 -2.4587 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5237 -0.9376 -1.1338 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2167 -1.6701 -3.2912 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1539 -1.4829 -2.7876 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1527 -3.1416 5.3911 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7520 -1.4476 5.6956 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5699 -2.6489 5.4260 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6292 -1.6111 1.2352 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8475 0.4072 1.9080 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9795 -1.3451 1.6683 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7391 -1.3667 -0.5149 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4674 -0.1284 -1.1936 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7895 1.4446 -0.7260 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5028 0.3875 0.4888 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9316 0.1656 1.3995 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1520 3.6922 3.8586 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0129 2.3769 5.0742 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4566 3.2722 4.6314 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3963 2.9405 1.0451 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7280 3.1465 -0.6709 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0349 2.5449 0.3730 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3481 2.2005 -0.3709 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4498 0.8068 1.3706 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0555 -0.9715 1.9574 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5900 -3.3184 1.5089 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4331 -3.8930 0.4364 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8448 -2.1715 -0.1443 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4427 2.4840 -2.4001 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6962 1.2734 -2.7313 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3395 0.7512 -3.9105 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6311 1.9907 -2.0627 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3080 -0.3640 -4.8562 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8287 1.2854 -5.2729 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5176 0.4802 -3.8550 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1300 -1.9321 -2.7576 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3940 -1.1299 -4.2597 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7790 -2.6584 -3.6248 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1150 -2.0662 -3.7561 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3616 -2.2511 -2.0189 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9360 -0.7400 -2.9412 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 10 16 1 1 10 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 17 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 28 34 1 0 34 35 1 0 34 36 1 0 34 37 1 0 11 5 1 0 26 21 1 0 9 35 1 6 29 9 1 0 1 38 1 0 1 39 1 0 1 40 1 0 5 41 1 6 6 42 1 0 6 43 1 0 7 44 1 6 8 45 1 0 8 46 1 0 8 47 1 0 11 48 1 6 15 49 1 0 15 50 1 0 15 51 1 0 16 52 1 0 16 53 1 0 16 54 1 0 17 55 1 1 22 56 1 0 23 57 1 0 24 58 1 0 25 59 1 0 26 60 1 0 27 61 1 0 27 62 1 0 28 63 1 6 29 64 1 1 33 65 1 0 33 66 1 0 33 67 1 0 36 68 1 0 36 69 1 0 36 70 1 0 37 71 1 0 37 72 1 0 37 73 1 0 M END

Standard InCHIKey	BGJHHQRHKDDKIR-OKPVOZINSA-N
Standard InCHI	InChI=1S/C28H36O9/c1-15-13-21(33-16(2)29)24(35-18(4)31)27(7)22(36-25(32)19-11-9-8-10-12-19)14-20-23(34-17(3)30)28(15,27)37-26(20,5)6/h8-12,15,20-24H,13-14H2,1-7H3/t15-,20-,21+,22+,23-,24+,27-,28-/m1/s1
SMILES	CC(=O)O[C@H]1C[C@@H](C)[C@@]23[C@]([C@H]1OC(=O)C)(C)[C@@H](OC(=O)c1ccccc1)C[C@H]([C@H]3OC(=O)C)C(O2)(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	516.24	Volume:	519.275 ? Van der Waals volume.
Dense:	0.994	LogP:	3.023 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.002 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.379 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	24.0
TPSA:	114.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.427	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.696	Fsp³:	0.643
MCE-18:	143.304 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.441	Fluc inhibitor:	0.145 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.005 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.295	Promiscuous compounds:	0.148

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.047	MDCK Permeability:	-4.744
Pgp-inhibitor:	0.97	Pgp-substrate:	0.234
PAMPA:	0.252 ? 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%):	0.155	30% Bioavailability (F30%):	0.33
50% Bioavailability (F50%):	0.951

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.34	MRP1:	1.0
Plasma Protein Binding (PPB):	76.512%	Volume Distribution (VD):	-0.341
Fu:	23.018% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.931	BCRP inhibitor:	0.083
BSEP inhibitor:	0.943

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.828
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.009
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.011	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.9 ? 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):

4.867

Half-life (T1/2):

0.518

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.343
Human Hepatotoxicity (H-HT):	0.212	Drug-induced Liver Injury (DILI):	0.884
AMES Toxicity:	0.465	Rat Oral Acute Toxicity:	0.265
Maximum Recommended Daily Dose:	0.206	Skin Sensitization:	0.994
Carcinogencity:	0.622	Eye Corrosion:	0.011
Eye Irritation:	0.565	Respiratory Toxicity:	0.089
Drug-induced Neurotoxicity:	0.256	Ototoxicity:	0.195
Hematotoxicity:	0.12	Drug-induced Nephrotoxicity:	0.344
Genotoxicity:	0.653	RPMI-8226 Immunitoxicity:	0.047
A549 Cytotoxicity:	0.231	Hek293 Cytotoxicity:	0.309
BCF:	0.574 ? 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:	3.571 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.124 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.631 ? 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]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10346948]
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]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170672]
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]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[11809076]
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]
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	stem	n.a.	PMID[15467233]
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]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	stem	n.a.	n.a.	PMID[18471021]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	n.a.	stem	n.a.	PMID[18471021]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[18507472]
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]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	Stems	n.a.	n.a.	PMID[19534471]
NPO10464	Epipedobates anthonyi	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20337496]
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]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23421714]
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]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27791375]
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]
NPO31542	Celastrus stephanotiifolius	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350085]
NPO31542	Celastrus stephanotiifolius	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	PMID[8350085]
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]
NPO23441	Schisandra sphaerandra	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[8778243]
NPO21610	Laurencia rigida	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358636]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461657]
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]
NPO20787	Achyranthes aspera	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22272	Raphanus raphanistrum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6425	Betula davurica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22788	Barnettia kerrii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3277	Salix alba	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21776	Sesbania grandiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21610	Laurencia rigida	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22212	Rhizophora mangle	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31542	Celastrus stephanotiifolius	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]
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20787	Achyranthes aspera	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20787	Achyranthes aspera	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23441	Schisandra sphaerandra	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5933	Drimia fugax	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21610	Laurencia rigida	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14938	Cybister lateralimarginalis	Species	Dytiscidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22212	Rhizophora mangle	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20787	Achyranthes aspera	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6425	Betula davurica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22788	Barnettia kerrii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10464	Epipedobates anthonyi	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19561	Garcinia conrauana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22670	Phebalium bilobum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23441	Schisandra sphaerandra	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22915	Stereocaulon azoreum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22272	Raphanus raphanistrum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17102	Ocypus olens	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3277	Salix alba	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22734	Neopringlea integrifolia	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5933	Drimia fugax	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21776	Sesbania grandiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6349	Celastrus orbiculatus	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	8
IC50	3
Ratio IC50	4

Activity Type	# Activity
Cell line	4
Others	8
Non-molecular	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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[8350085]
NPT80	Cell line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[8350085]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	41300.0	nM	PMID[10346948]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	34800.0	nM	PMID[10346948]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	400.0	nM	PMID[10346948]
NPT2	Others	Unspecified	n.a.	Activity	=	34.2	%	PMID[8350085]
NPT2	Others	Unspecified	n.a.	Activity	=	65.9	%	PMID[8350085]
NPT2	Others	Unspecified	n.a.	Activity	=	92.9	%	PMID[8350085]
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	PMID[8350085]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	87.0	n.a.	PMID[10346948]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	8.3	n.a.	PMID[10346948]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	2.3	n.a.	PMID[10346948]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	3.7	n.a.	PMID[10346948]

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 NPC195647 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	18731
0.1-0.2	29225
0.2-0.3	1375
0.3-0.4	348
0.4-0.5	92
0.5-0.6	51
0.6-0.7	17
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9273	High Similarity	NPC473081
0.9273	High Similarity	NPC200592
0.9273	High Similarity	NPC610542
0.8596	High Similarity	NPC270498
0.8	Intermediate Similarity	NPC473112
0.8	Intermediate Similarity	NPC607428
0.7778	Intermediate Similarity	NPC43241
0.7619	Intermediate Similarity	NPC479047
0.7619	Intermediate Similarity	NPC291638
0.7538	Intermediate Similarity	NPC472574
0.7391	Intermediate Similarity	NPC14499
0.7385	Intermediate Similarity	NPC473673
0.7231	Intermediate Similarity	NPC139067
0.7231	Intermediate Similarity	NPC177340
0.7213	Intermediate Similarity	NPC474608
0.7206	Intermediate Similarity	NPC473613
0.7206	Intermediate Similarity	NPC473085
0.7077	Intermediate Similarity	NPC4341
0.7015	Intermediate Similarity	NPC479044
0.6984	Remote Similarity	NPC481047
0.6984	Remote Similarity	NPC481045
0.6901	Remote Similarity	NPC88593
0.6818	Remote Similarity	NPC483883
0.6818	Remote Similarity	NPC151585
0.6716	Remote Similarity	NPC67777
0.6667	Remote Similarity	NPC70973
0.6667	Remote Similarity	NPC283375
0.6571	Remote Similarity	NPC184747
0.6567	Remote Similarity	NPC191082
0.6418	Remote Similarity	NPC473111
0.6406	Remote Similarity	NPC183122
0.6197	Remote Similarity	NPC609924
0.6154	Remote Similarity	NPC481066
0.6087	Remote Similarity	NPC48017
0.6	Remote Similarity	NPC147217
0.6	Remote Similarity	NPC27377
0.5942	Remote Similarity	NPC17877
0.5942	Remote Similarity	NPC163087
0.589	Remote Similarity	NPC210591
0.5857	Remote Similarity	NPC147880
0.5775	Remote Similarity	NPC158663
0.5775	Remote Similarity	NPC148062
0.5735	Remote Similarity	NPC475429
0.5735	Remote Similarity	NPC476094
0.5733	Remote Similarity	NPC481050
0.5733	Remote Similarity	NPC609221
0.5714	Remote Similarity	NPC473060
0.5694	Remote Similarity	NPC471100
0.5694	Remote Similarity	NPC605884
0.5676	Remote Similarity	NPC97667
0.5634	Remote Similarity	NPC246480
0.5616	Remote Similarity	NPC41481
0.5616	Remote Similarity	NPC92293
0.56	Remote Similarity	NPC475652
0.5584	Remote Similarity	NPC608007
0.5556	Remote Similarity	NPC270590
0.5513	Remote Similarity	NPC605086
0.5507	Remote Similarity	NPC211137
0.5507	Remote Similarity	NPC66761
0.5507	Remote Similarity	NPC483843
0.55	Remote Similarity	NPC75600
0.55	Remote Similarity	NPC483884
0.5479	Remote Similarity	NPC254558
0.5479	Remote Similarity	NPC471107
0.5467	Remote Similarity	NPC70716
0.5467	Remote Similarity	NPC95265
0.5455	Remote Similarity	NPC475039
0.5443	Remote Similarity	NPC483865
0.5375	Remote Similarity	NPC56953
0.5352	Remote Similarity	NPC483879
0.5342	Remote Similarity	NPC137718
0.5333	Remote Similarity	NPC266265
0.5278	Remote Similarity	NPC483902
0.5278	Remote Similarity	NPC51314
0.5278	Remote Similarity	NPC159520
0.5278	Remote Similarity	NPC472577
0.527	Remote Similarity	NPC473758
0.5256	Remote Similarity	NPC483887
0.5256	Remote Similarity	NPC158020
0.5256	Remote Similarity	NPC476035
0.5195	Remote Similarity	NPC36021
0.5139	Remote Similarity	NPC481067
0.5139	Remote Similarity	NPC475759
0.5132	Remote Similarity	NPC479043
0.5128	Remote Similarity	NPC479042
0.5122	Remote Similarity	NPC483870
0.5067	Remote Similarity	NPC171207

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC195647 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4373
0.1-0.2	4619
0.2-0.3	158
0.3-0.4	0
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