NPASS Compound

Natural Product: NPC205673

Natural Product ID	NPC205673
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UMRPOGLIBDXFNK-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	345510
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 86 90 0 0 0 0 0 0 0 0999 V2000 7.9550 -0.1116 2.2179 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0323 0.5831 1.2968 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4753 1.5726 0.6542 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7098 0.2150 1.0949 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8565 0.9067 0.2028 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7438 1.6076 0.9499 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7407 0.6231 1.5334 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2639 -0.3798 0.5695 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7205 -1.7537 1.1172 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8647 -0.2497 -0.8214 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1478 0.7197 -1.6901 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9071 1.3338 -1.1933 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0463 0.5768 -0.2586 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4242 1.5486 0.8320 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8059 -0.5615 0.3701 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0705 -1.1664 1.5514 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3884 -1.0495 1.3507 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0070 -0.5606 0.2994 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4944 -0.5484 0.3323 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9977 0.4965 1.3112 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5077 0.4593 1.3478 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9993 1.4237 2.4212 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9965 -0.9014 1.7064 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9487 0.9343 -0.0177 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5534 -0.0796 -1.0174 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1100 -0.4999 -1.0132 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1679 -1.9592 -1.5224 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3755 0.3145 -2.0250 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0527 0.8690 -1.6497 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1940 -0.0485 -0.8535 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8647 -1.2345 -1.7342 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3600 -0.0650 -0.8272 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7199 0.5413 -2.1962 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1021 -1.3863 -0.7692 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3967 -0.7633 2.9211 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7120 -0.6837 1.6253 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5672 0.6518 2.7810 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4752 1.7340 -0.2396 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2461 2.1158 1.8266 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2900 2.4111 0.3744 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2942 0.1777 2.4188 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9638 1.2507 2.0152 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4392 -2.5656 0.4535 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7891 -1.7247 1.4112 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1861 -1.8164 2.1138 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7003 -1.2731 -1.2835 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8808 1.5565 -1.9099 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9836 0.2958 -2.7286 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1752 2.3395 -0.7380 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3241 1.6734 -2.1039 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2611 2.4521 0.8351 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4135 1.1352 1.8336 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4092 1.9623 0.6374 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7496 -1.3993 -0.3984 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2556 -2.2746 1.6194 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3381 -0.6655 2.4932 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9964 -1.4221 2.1937 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7964 -1.5278 0.8150 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7305 1.5194 0.9397 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5835 0.2597 2.2939 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4945 1.1326 3.3585 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0878 1.1740 2.5719 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8550 2.4751 2.1445 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8981 -1.6648 0.9396 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0502 -0.9026 2.0602 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3690 -1.2520 2.5781 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3698 1.8738 -0.2191 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0253 1.0821 -0.0583 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7895 0.3444 -2.0391 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2692 -0.9447 -0.9309 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3527 -2.5385 -1.0308 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1090 -2.4391 -1.1883 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1060 -1.9776 -2.6252 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0113 1.1986 -2.3426 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2980 -0.2651 -2.9953 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5146 1.0448 -2.6330 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1810 1.8833 -1.2341 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5910 -1.2997 -2.5988 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1032 -1.1099 -2.2805 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9497 -2.2070 -1.2104 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0150 0.2495 -2.9760 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7211 0.1361 -2.5380 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9005 1.6364 -2.1105 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7889 -1.4413 0.1267 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4340 -2.2613 -0.8361 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8201 -1.5158 -1.6335 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 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 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 26 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 10 32 1 0 32 33 1 0 32 34 1 0 32 5 1 0 15 8 1 0 30 18 1 0 30 13 1 0 26 19 1 0 1 35 1 0 1 36 1 0 1 37 1 0 5 38 1 0 6 39 1 0 6 40 1 0 7 41 1 0 7 42 1 0 9 43 1 0 9 44 1 0 9 45 1 0 10 46 1 0 11 47 1 0 11 48 1 0 12 49 1 0 12 50 1 0 14 51 1 0 14 52 1 0 14 53 1 0 15 54 1 0 16 55 1 0 16 56 1 0 17 57 1 0 19 58 1 0 20 59 1 0 20 60 1 0 22 61 1 0 22 62 1 0 22 63 1 0 23 64 1 0 23 65 1 0 23 66 1 0 24 67 1 0 24 68 1 0 25 69 1 0 25 70 1 0 27 71 1 0 27 72 1 0 27 73 1 0 28 74 1 0 28 75 1 0 29 76 1 0 29 77 1 0 31 78 1 0 31 79 1 0 31 80 1 0 33 81 1 0 33 82 1 0 33 83 1 0 34 84 1 0 34 85 1 0 34 86 1 0 M END

Standard InCHIKey	UMRPOGLIBDXFNK-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C32H52O2/c1-21(33)34-26-13-14-30(7)24(28(26,4)5)12-15-32(9)25(30)11-10-22-23-20-27(2,3)16-17-29(23,6)18-19-31(22,32)8/h10,23-26H,11-20H2,1-9H3
SMILES	CC(=O)OC1CCC2(C)C(CCC3(C)C2CC=C2C4CC(C)(C)CCC4(C)CCC32C)C1(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	468.4	Volume:	531.553 ? Van der Waals volume.
Dense:	0.881	LogP:	6.546 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.084 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.278 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	26.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.284	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.587	Fsp³:	0.906
MCE-18:	103.574 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.53	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.726	Promiscuous compounds:	0.009

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.978	MDCK Permeability:	-4.787
Pgp-inhibitor:	0.991	Pgp-substrate:	0.0
PAMPA:	0.003 ? 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%):	0.004	30% Bioavailability (F30%):	0.027
50% Bioavailability (F50%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992	MRP1:	1.0
Plasma Protein Binding (PPB):	97.545%	Volume Distribution (VD):	0.344
Fu:	3.023% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.097
OATP1B3 inhibitor:	0.65	BCRP inhibitor:	0.005
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.02	CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.872
CYP2C9-inhibitor:	0.092	CYP2C9-substrate:	0.347
CYP2D6-inhibitor:	0.05	CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.61	CYP3A4-substrate:	0.006
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	0.999
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):

8.02

Half-life (T1/2):

0.389

ADMET: Toxicity

hERG Blockers:	0.103	hERG Blockers (10um):	0.69
Human Hepatotoxicity (H-HT):	0.356	Drug-induced Liver Injury (DILI):	0.148
AMES Toxicity:	0.057	Rat Oral Acute Toxicity:	0.13
Maximum Recommended Daily Dose:	0.735	Skin Sensitization:	0.544
Carcinogencity:	0.298	Eye Corrosion:	0.111
Eye Irritation:	0.66	Respiratory Toxicity:	0.498
Drug-induced Neurotoxicity:	0.381	Ototoxicity:	0.755
Hematotoxicity:	0.15	Drug-induced Nephrotoxicity:	0.048
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.027
A549 Cytotoxicity:	0.307	Hek293 Cytotoxicity:	0.33
BCF:	2.61 ? 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:	5.45 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.896 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.561 ? 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
NPO29042	Vincetoxicum atratum	Species	Apocynaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11374953]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	flower	n.a.	PMID[15481244]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[16792421]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17156960]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	whole plants	Panshi, Jilin Province, China	2009-JUN	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21534540]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[24660966]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25453801]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26422318]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26702644]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28218000]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28294615]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28383891]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29148766]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30676026]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184480]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23674	Jatropha curcas	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29042	Vincetoxicum atratum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23674	Jatropha curcas	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23674	Jatropha curcas	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29042	Vincetoxicum atratum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO842	Vincetoxicum versicolor	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29042	Vincetoxicum atratum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23674	Jatropha curcas	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29042	Vincetoxicum atratum	Species	Apocynaceae	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

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

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 NPC205673 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	23531
0.1-0.2	21749
0.2-0.3	3399
0.3-0.4	912
0.4-0.5	209
0.5-0.6	30
0.6-0.7	13
0.7-0.8	0
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC195334
0.8704	High Similarity	NPC224145
0.8421	Intermediate Similarity	NPC10005
0.8421	Intermediate Similarity	NPC91525
0.8246	Intermediate Similarity	NPC162107
0.8246	Intermediate Similarity	NPC46912
0.8103	Intermediate Similarity	NPC191965
0.7966	Intermediate Similarity	NPC286786
0.7544	Intermediate Similarity	NPC290495
0.7049	Intermediate Similarity	NPC137306
0.7	Intermediate Similarity	NPC480944
0.6818	Remote Similarity	NPC488520
0.6615	Remote Similarity	NPC488523
0.6462	Remote Similarity	NPC23621
0.6441	Remote Similarity	NPC142754
0.6418	Remote Similarity	NPC488525
0.6406	Remote Similarity	NPC329943
0.6364	Remote Similarity	NPC120840
0.6271	Remote Similarity	NPC290598
0.6271	Remote Similarity	NPC30590
0.625	Remote Similarity	NPC127855
0.6154	Remote Similarity	NPC9892
0.6143	Remote Similarity	NPC86368
0.6143	Remote Similarity	NPC488522
0.5972	Remote Similarity	NPC488524
0.5873	Remote Similarity	NPC235341
0.5857	Remote Similarity	NPC488521
0.5735	Remote Similarity	NPC470590
0.5735	Remote Similarity	NPC285184
0.5714	Remote Similarity	NPC196753
0.5645	Remote Similarity	NPC474488
0.5606	Remote Similarity	NPC246708
0.5571	Remote Similarity	NPC113989
0.5556	Remote Similarity	NPC108476
0.5538	Remote Similarity	NPC470588
0.5493	Remote Similarity	NPC477875
0.5484	Remote Similarity	NPC601696
0.5455	Remote Similarity	NPC267517
0.5385	Remote Similarity	NPC471899
0.5385	Remote Similarity	NPC478657
0.5352	Remote Similarity	NPC485589
0.5278	Remote Similarity	NPC294360
0.527	Remote Similarity	NPC477876
0.5231	Remote Similarity	NPC101475
0.5217	Remote Similarity	NPC136313
0.5147	Remote Similarity	NPC231431
0.5139	Remote Similarity	NPC471896
0.5075	Remote Similarity	NPC3915
0.5075	Remote Similarity	NPC608979
0.5068	Remote Similarity	NPC78580
0.5068	Remote Similarity	NPC481363
0.5067	Remote Similarity	NPC485586
0.5067	Remote Similarity	NPC485588
0.5059	Remote Similarity	NPC214484

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC205673 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7378
0.1-0.2	1723
0.2-0.3	41
0.3-0.4	3
0.4-0.5	4
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