NPASS Compound

Natural Product: NPC120096

Natural Product ID	NPC120096
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LLWMPGSQZXZZAE-JZFVXYNCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	3034636
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids

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 69 73 0 0 0 0 0 0 0 0999 V2000 -3.3555 1.1552 -3.0566 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6175 1.7096 -1.6948 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4531 2.7552 -1.6336 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7810 3.3771 -0.3563 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5654 4.3584 -0.2998 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1672 2.8190 0.8428 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4179 3.3199 1.9703 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2548 1.6645 0.6999 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0061 1.1548 -0.4938 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1260 0.0815 -0.3927 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8536 -0.1895 0.9701 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5117 0.9206 1.7482 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4342 -1.5184 1.3043 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9048 -1.5050 0.9308 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7646 -2.5721 0.5009 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2705 -2.5429 0.5344 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2331 -1.1678 0.2978 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7348 -1.0867 0.1457 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4884 -1.4448 1.3707 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1191 -2.0910 -0.9309 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5440 -1.9370 -1.3846 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9618 -0.5725 -1.7369 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4116 0.5204 -0.8568 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3338 1.7674 -1.7602 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3883 0.8295 0.2125 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0082 0.2629 -0.4170 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4829 1.4038 0.3919 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1698 1.2277 1.0268 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3432 -0.1436 1.2334 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2002 -0.5410 2.6965 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3612 -0.5132 -1.6798 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4364 0.5384 -3.0041 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2037 0.4367 -3.2473 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3294 1.9182 -3.8358 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8977 3.1535 -2.5378 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2524 0.4687 2.4695 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8162 1.5350 2.3191 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3846 -1.7994 2.3677 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1133 -0.9970 -0.0097 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5279 -1.0289 1.7419 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3061 -2.5525 0.8523 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1514 -2.5306 -0.5364 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0882 -3.5737 0.8985 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0521 -3.1725 -0.3494 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1616 -3.0560 1.4150 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1607 -0.8706 -0.7241 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0936 -2.4335 1.7271 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4308 -0.7639 2.2070 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5438 -1.6304 1.1079 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0825 -3.1091 -0.4386 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4288 -2.0475 -1.7961 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2285 -2.4159 -0.6451 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6388 -2.5834 -2.3068 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7024 -0.3830 -2.8111 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3495 1.8769 -2.2125 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0924 1.7175 -2.5661 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5709 2.6773 -1.1707 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8080 1.8788 0.1513 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3136 0.1853 0.1174 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0529 0.7095 1.2393 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4076 0.2765 -1.3834 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4637 2.3025 -0.2921 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2616 1.6711 1.1390 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6030 1.8142 0.4597 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1923 1.7515 2.0304 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1521 -0.4473 3.2628 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4840 0.1869 3.2286 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1368 -1.5801 2.8227 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7170 0.3747 -1.8734 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 4 6 1 0 6 7 2 0 6 8 1 0 8 9 2 0 9 10 1 0 11 10 1 6 11 12 1 0 11 13 1 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 1 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 23 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 1 22 31 1 0 9 2 1 0 29 11 1 0 12 8 1 0 29 17 1 0 26 18 1 0 1 32 1 0 1 33 1 0 1 34 1 0 3 35 1 0 12 36 1 0 12 37 1 0 13 38 1 1 14 39 1 0 14 40 1 0 14 41 1 0 15 42 1 0 15 43 1 0 16 44 1 0 16 45 1 0 17 46 1 6 19 47 1 0 19 48 1 0 19 49 1 0 20 50 1 0 20 51 1 0 21 52 1 0 21 53 1 0 22 54 1 6 24 55 1 0 24 56 1 0 24 57 1 0 25 58 1 0 25 59 1 0 25 60 1 0 26 61 1 6 27 62 1 0 27 63 1 0 28 64 1 0 28 65 1 0 30 66 1 0 30 67 1 0 30 68 1 0 31 69 1 0 M END

Standard InCHIKey	LLWMPGSQZXZZAE-JZFVXYNCSA-N
Standard InCHI	InChI=1S/C27H38O4/c1-15-13-18(28)22(30)17-14-27(31-23(15)17)16(2)7-8-20-25(5)11-10-21(29)24(3,4)19(25)9-12-26(20,27)6/h13,16,19-21,29H,7-12,14H2,1-6H3/t16-,19-,20+,21-,25-,26+,27-/m0/s1
SMILES	CC1=CC(=O)C(=O)C2=C1O[C@@]1(C2)[C@@H](C)CC[C@@H]2[C@@]3(C)CC[C@@H](C(C)(C)[C@@H]3CC[C@@]12C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	426.28	Volume:	457.381 ? Van der Waals volume.
Dense:	0.932	LogP:	2.552 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.734 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.145 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	28.0
TPSA:	63.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.43	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.196	Fsp³:	0.778
MCE-18:	130.5 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	1
Colloidal aggregators:	0.657	Fluc inhibitor:	0.35 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.087 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.382	Promiscuous compounds:	0.353

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.165	MDCK Permeability:	-4.849
Pgp-inhibitor:	0.651	Pgp-substrate:	0.002
PAMPA:	0.982 ? 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):	0.013
20% Bioavailability (F20%):	0.335	30% Bioavailability (F30%):	0.289
50% Bioavailability (F50%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.783
Plasma Protein Binding (PPB):	98.62%	Volume Distribution (VD):	-0.018
Fu:	1.367% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.005
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.892	CYP1A2-substrate:	0.603
CYP2C19-inhibitor:	0.792	CYP2C19-substrate:	0.853
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.06	CYP3A4-substrate:	0.544
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.955
HLM stability:	0.684 ? 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):

8.973

Half-life (T1/2):

0.509

ADMET: Toxicity

hERG Blockers:	0.026	hERG Blockers (10um):	0.187
Human Hepatotoxicity (H-HT):	0.872	Drug-induced Liver Injury (DILI):	0.725
AMES Toxicity:	0.746	Rat Oral Acute Toxicity:	0.573
Maximum Recommended Daily Dose:	0.816	Skin Sensitization:	0.997
Carcinogencity:	0.962	Eye Corrosion:	0.081
Eye Irritation:	0.865	Respiratory Toxicity:	0.674
Drug-induced Neurotoxicity:	0.108	Ototoxicity:	0.384
Hematotoxicity:	0.84	Drug-induced Nephrotoxicity:	0.876
Genotoxicity:	0.922	RPMI-8226 Immunitoxicity:	0.138
A549 Cytotoxicity:	0.22	Hek293 Cytotoxicity:	0.669
BCF:	1.891 ? 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:	4.761 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.489 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.896 ? 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
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s11306-014-0728-9]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1038/sdata.2014.29]
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	Roots	Mexican	n.a.	PMID[10479311]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11171227]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12576668]
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	crude resin	Mexican	n.a.	PMID[16562846]
NPO14765	Lyngbya sordida	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18444683]
NPO9164	Catunaregam spinosa	Species	Rubiaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[21861991]
NPO14026.1	Vitex negundo var. cannabifolia	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25245917]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	seed	n.a.	PMID[25891114]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987503]
NPO7107	Garcinia spicata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14765	Lyngbya sordida	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9580	Astragalus cephalotes	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9164	Catunaregam spinosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14026.1	Vitex negundo var. cannabifolia	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16005	Ostracion immaculatus	Species	Ostraciidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18614	Gentiana turkestanorum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20669	Baccharis rhetinodes	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19772	Ceroplastes ceriferus	Species	Coccidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21549	Consolida raveyi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4243	Didymocarpus leucocalyx	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16442	Omphalia campanella	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14033	Torilis arvensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20473	Vaccinium membranaceum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	Database[MetaboLights]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18614	Gentiana turkestanorum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14765	Lyngbya sordida	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16005	Ostracion immaculatus	Species	Ostraciidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21549	Consolida raveyi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20669	Baccharis rhetinodes	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9580	Astragalus cephalotes	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18614	Gentiana turkestanorum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9164	Catunaregam spinosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14033	Torilis arvensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4243	Didymocarpus leucocalyx	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14026.1	Vitex negundo var. cannabifolia	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7107	Garcinia spicata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20473	Vaccinium membranaceum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16442	Omphalia campanella	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19772	Ceroplastes ceriferus	Species	Coccidae	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 NPC120096 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	18308
0.1-0.2	27930
0.2-0.3	3326
0.3-0.4	292
0.4-0.5	2
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC478052

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC120096 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7132
0.1-0.2	1907
0.2-0.3	109
0.3-0.4	2
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