NPASS Compound

Natural Product: NPC189689

Natural Product ID	NPC189689
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Gambogenic Acid
IUPAC Name	n.a.
Synonyms	Gambogenic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2205166
PubChem CID	10794070
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

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 91 95 0 0 0 0 0 0 0 0999 V2000 7.6851 -1.7360 -4.3521 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2640 -0.4322 -3.7857 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2634 -0.3551 -2.8863 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5696 -1.5794 -2.4516 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7026 -1.9065 -1.0117 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2006 -0.9289 -0.0450 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2088 -1.2636 0.7926 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6138 -0.3891 1.8040 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1608 -0.1762 1.5968 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2846 -1.2026 1.9305 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0580 -1.0101 1.7464 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0304 -2.0824 2.0856 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2218 -2.1668 3.5472 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0558 -3.2296 4.2975 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6334 -4.5616 3.7576 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3077 -3.0942 5.7817 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6069 0.1890 1.2301 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2910 1.1838 0.9108 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6406 1.0026 1.0904 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5070 2.0370 0.7519 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2960 2.4188 0.3947 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4539 3.3755 0.0779 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7393 2.5578 0.2419 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3319 3.6270 -0.2751 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8104 3.6913 0.0435 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8877 3.3945 1.5395 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5363 1.9770 1.8357 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6926 1.0378 1.6876 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0230 1.6948 1.9423 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5183 -0.0608 2.7216 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6122 0.4366 0.4408 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7304 1.1854 -0.3172 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2219 0.4453 -1.5404 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2926 0.0553 -2.4416 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4806 0.4215 -3.6874 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6932 -0.1267 -4.4449 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6083 1.3175 -4.3714 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6021 1.8488 -3.9009 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9019 1.6394 -5.7037 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3741 2.4791 -0.6448 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2954 2.6448 -1.4022 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6251 1.4625 0.6913 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9676 0.3033 1.0742 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7964 -2.3886 2.4390 O 0 0 0 0 0 1 0 0 0 0 0 0 5.7660 0.4241 0.0786 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9681 0.7990 -4.2280 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9879 -2.4516 -3.5354 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8746 -2.1920 -4.9639 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5593 -1.6086 -4.9929 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0085 0.6312 -2.5350 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9754 -2.4444 -3.0557 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5054 -1.5093 -2.7899 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8106 -2.0871 -0.8314 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2559 -2.9061 -0.7682 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8173 -2.2705 0.7083 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7672 -0.7801 2.8394 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0538 0.6410 1.8364 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6838 -3.0722 1.7246 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0090 -1.9129 1.5630 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5364 -1.2342 4.0489 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5711 -5.0214 3.3254 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1282 -4.4483 2.9797 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2984 -5.2403 4.5431 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4257 -3.5030 6.3142 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1533 -3.7913 5.9843 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5624 -2.0700 6.0431 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7479 2.1308 -0.2288 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8376 4.3725 -0.8559 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2722 4.6241 -0.2448 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8580 3.7131 1.9665 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1098 4.0430 2.0125 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0043 1.8464 2.8092 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9617 2.1238 2.9793 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2837 2.4579 1.1966 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7933 0.8946 1.8685 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1982 -1.0278 2.2454 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7749 0.2454 3.5129 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4740 -0.2751 3.2270 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6648 -0.4542 -1.1443 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4796 1.0766 -2.0031 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0861 -0.6500 -2.0713 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9880 -1.0742 -3.9843 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4862 0.6432 -4.3566 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3909 -0.3087 -5.4796 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2852 2.2412 -6.2392 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8122 0.4807 -0.3452 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1746 1.2213 -0.4077 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9534 0.6882 1.1708 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9829 0.5200 -4.6037 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1308 1.5207 -3.4168 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4212 1.2583 -5.0873 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 3 14 15 1 0 14 16 1 0 11 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 18 21 1 0 21 22 2 0 21 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 28 31 1 0 31 32 1 0 32 33 1 6 33 34 1 0 34 35 2 0 35 36 1 0 35 37 1 0 37 38 2 0 37 39 1 0 32 40 1 0 40 41 2 0 32 42 1 0 42 43 1 1 10 44 1 0 6 45 1 0 2 46 1 0 19 9 1 0 42 23 1 0 43 17 1 0 40 25 1 0 42 27 1 0 1 47 1 0 1 48 1 0 1 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 5 53 1 0 5 54 1 0 7 55 1 0 8 56 1 0 8 57 1 0 12 58 1 0 12 59 1 0 13 60 1 0 15 61 1 0 15 62 1 0 15 63 1 0 16 64 1 0 16 65 1 0 16 66 1 0 20 67 1 0 24 68 1 0 25 69 1 1 26 70 1 0 26 71 1 0 27 72 1 1 29 73 1 0 29 74 1 0 29 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 33 79 1 0 33 80 1 0 34 81 1 0 36 82 1 0 36 83 1 0 36 84 1 0 39 85 1 0 45 86 1 0 45 87 1 0 45 88 1 0 46 89 1 0 46 90 1 0 46 91 1 0 M CHG 1 44 -1 M END

Standard InCHIKey	RCWNBHCZYXWDOV-VSFMGBBVSA-N
Standard InCHI	InChI=1S/C38H46O8/c1-20(2)10-9-11-22(5)13-15-25-30(39)26(14-12-21(3)4)33-29(31(25)40)32(41)27-18-24-19-28-36(7,8)46-37(34(24)42,38(27,28)45-33)17-16-23(6)35(43)44/h10,12-13,16,18,24,28,39-40H,9,11,14-15,17,19H2,1-8H3,(H,43,44)/p-1/b22-13+,23-16-/t24-,28+,37+,38-/m1/s1
SMILES	CC(=CCC/C(=C/Cc1c(c(CC=C(C)C)c2c(c1O)C(=O)C1=C[C@@H]3C[C@H]4C(C)(C)O[C@@](C/C=C(/C)C(=O)O)(C3=O)[C@@]14O2)[O-])/C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	630.32	Volume:	664.342 ? Van der Waals volume.
Dense:	0.949	LogP:	6.716 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.244 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.681 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	29.0
TPSA:	130.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.182	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.441	Fsp³:	0.5
MCE-18:	168.421 ? 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:	0.949	Fluc inhibitor:	0.177 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.677 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.939 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.332	Promiscuous compounds:	0.257

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.138	MDCK Permeability:	-4.769
Pgp-inhibitor:	0.855	Pgp-substrate:	0.002
PAMPA:	0.951 ? 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):	0.125
20% Bioavailability (F20%):	0.996	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.995
Plasma Protein Binding (PPB):	97.069%	Volume Distribution (VD):	0.016
Fu:	2.467% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.585	BCRP inhibitor:	0.032
BSEP inhibitor:	0.93

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.155	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.013	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.335	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

1.802

Half-life (T1/2):

1.456

ADMET: Toxicity

hERG Blockers:	0.031	hERG Blockers (10um):	0.154
Human Hepatotoxicity (H-HT):	0.959	Drug-induced Liver Injury (DILI):	0.956
AMES Toxicity:	0.219	Rat Oral Acute Toxicity:	0.961
Maximum Recommended Daily Dose:	0.775	Skin Sensitization:	0.994
Carcinogencity:	0.154	Eye Corrosion:	0.0
Eye Irritation:	0.007	Respiratory Toxicity:	0.97
Drug-induced Neurotoxicity:	0.276	Ototoxicity:	0.981
Hematotoxicity:	0.893	Drug-induced Nephrotoxicity:	0.972
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.219
A549 Cytotoxicity:	0.238	Hek293 Cytotoxicity:	0.29
BCF:	1.794 ? 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:	5.507 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.593 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.074 ? 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
NPO17342	Microcosmus vulgaris	Species	Pyuridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10785429]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	latex	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	resin	n.a.	n.a.	PMID[19072548]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21486005]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17093	Callitriche stagnalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13703	Croton discolor	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4477	Fasciola hepatica	Species	Fasciolidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19760	Fragaria chiloensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20810	Lobaria adusta	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17342	Microcosmus vulgaris	Species	Pyuridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19429	Millettia auriculata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22632	Pteris glauca	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28098	Rhizomnium pseudopunctatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11950	Ruscus hypoglossum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14692	Salix babylonica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19300	Scleroderma tinctorium	Species	Sclerodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18834	Scrophularia glabrata	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19508	Toxicodendron radicans	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15765	Vernonanthura discolor	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18593	Wrightia coccinea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14692	Salix babylonica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19429	Millettia auriculata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19429	Millettia auriculata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19508	Toxicodendron radicans	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14692	Salix babylonica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14692	Salix babylonica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13703	Croton discolor	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17093	Callitriche stagnalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18593	Wrightia coccinea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17342	Microcosmus vulgaris	Species	Pyuridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4477	Fasciola hepatica	Species	Fasciolidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14692	Salix babylonica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18834	Scrophularia glabrata	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28098	Rhizomnium pseudopunctatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19508	Toxicodendron radicans	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15765	Vernonanthura discolor	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11950	Ruscus hypoglossum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20810	Lobaria adusta	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19300	Scleroderma tinctorium	Species	Sclerodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22632	Pteris glauca	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19429	Millettia auriculata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19760	Fragaria chiloensis	Species	Rosaceae	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	5
Ki	1

Activity Type	# Activity
Individual protein	2
Cell line	3
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	3470.0	nM	PMID[28318895]
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Ki	=	1210.0	nM	PMID[28318895]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell line	A549	Homo sapiens	IC50	=	3490.0	nM	DOI[10.1039/C4MD00407H]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	3230.0	nM	DOI[10.1039/C4MD00407H]
NPT380	Cell line	U-251	Homo sapiens	IC50	=	3220.0	nM	DOI[10.1039/C4MD00407H]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	4160.0	nM	DOI[10.1039/C4MD00407H]

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 NPC189689 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	12459
0.1-0.2	35922
0.2-0.3	1379
0.3-0.4	44
0.4-0.5	26
0.5-0.6	13
0.6-0.7	7
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8352	Intermediate Similarity	NPC611384
0.7959	Intermediate Similarity	NPC162248
0.75	Intermediate Similarity	NPC158329
0.75	Intermediate Similarity	NPC55422
0.75	Intermediate Similarity	NPC75141
0.7263	Intermediate Similarity	NPC40089
0.7263	Intermediate Similarity	NPC47634
0.72	Intermediate Similarity	NPC476216
0.6882	Remote Similarity	NPC286422
0.6882	Remote Similarity	NPC603867
0.6796	Remote Similarity	NPC476146
0.6476	Remote Similarity	NPC41598
0.6038	Remote Similarity	NPC601073
0.6038	Remote Similarity	NPC609328
0.6019	Remote Similarity	NPC610447
0.5979	Remote Similarity	NPC131578
0.5979	Remote Similarity	NPC611483
0.5842	Remote Similarity	NPC476255
0.5806	Remote Similarity	NPC94796
0.5806	Remote Similarity	NPC611777
0.578	Remote Similarity	NPC476229
0.578	Remote Similarity	NPC476152
0.5686	Remote Similarity	NPC223413
0.5607	Remote Similarity	NPC476311
0.5315	Remote Similarity	NPC476210
0.5204	Remote Similarity	NPC607281
0.52	Remote Similarity	NPC608101
0.5135	Remote Similarity	NPC233978

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC189689 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4038
0.1-0.2	5089
0.2-0.3	23
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