NPASS Compound

Natural Product: NPC140864

Natural Product ID	NPC140864
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UTSCVCXUBUMWOX-ICDOJPABSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101290462
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000260] Monohydroxy bile acids, alcohols and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 66 69 0 0 0 0 0 0 0 0999 V2000 4.9526 -0.9287 1.4221 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7544 0.2946 0.6153 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6535 0.4025 -0.3173 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7086 -0.6452 -1.4586 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3539 -0.5090 -2.1231 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5956 0.4444 -1.2601 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8931 1.8278 -1.7609 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1532 0.1774 -1.1309 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6477 0.0430 -2.1862 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1019 -0.2236 -2.1381 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5896 0.2397 -0.7870 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0504 0.2949 -0.5957 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8343 0.2128 -1.8928 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4399 1.6616 -0.0013 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6246 -0.7360 0.3520 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8115 -0.9799 1.5729 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4470 -0.3836 1.5926 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8057 -0.5142 0.2387 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6313 -1.9869 -0.0343 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4321 0.0575 0.1965 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2171 0.4243 1.2877 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6205 0.9859 1.1246 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2515 0.1540 0.0971 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9369 -1.3063 0.3819 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0242 -1.8890 -0.3241 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9344 1.5032 1.4338 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1099 2.4338 1.5609 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1288 1.6910 2.1701 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9271 -0.7681 1.9860 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2293 -1.1137 2.2250 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1866 -1.8050 0.7827 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7105 0.3141 -0.0596 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7085 1.3763 -0.8419 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5424 -0.3314 -2.1483 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9649 -1.6360 -1.1154 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8650 -1.4645 -2.3370 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5443 -0.0416 -3.1336 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6928 1.8748 -2.5279 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0818 2.5793 -1.0088 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9594 2.1614 -2.3041 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1557 0.1440 -3.1555 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5570 0.4904 -2.8895 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4176 -1.2100 -2.4468 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2161 1.3166 -0.7555 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9074 0.3582 -1.6276 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5476 1.1284 -2.4804 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6377 -0.6976 -2.4609 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6661 2.4197 -0.2514 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3974 2.0147 -0.3790 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4785 1.6086 1.1034 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6077 -0.2942 0.7098 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3186 -0.6015 2.5131 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8106 -2.0975 1.7457 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4212 0.6343 1.9960 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8237 -1.0126 2.2943 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4813 -2.6128 0.2995 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3896 -2.2544 -1.0587 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7649 -2.3903 0.5750 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2628 0.3143 2.2311 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0462 0.8803 2.1472 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4795 2.0472 0.9378 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3293 -1.7908 -0.4153 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2742 -1.3724 1.2898 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8307 -1.9430 0.4919 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7340 -1.5886 -0.9715 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3992 2.6173 2.4807 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 6 6 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 6 18 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 1 15 25 1 0 2 26 1 0 26 27 2 0 26 28 1 0 23 3 1 0 23 6 1 0 20 8 1 0 18 11 1 0 1 29 1 0 1 30 1 0 1 31 1 0 2 32 1 6 3 33 1 6 4 34 1 0 4 35 1 0 5 36 1 0 5 37 1 0 7 38 1 0 7 39 1 0 7 40 1 0 9 41 1 0 10 42 1 0 10 43 1 0 11 44 1 1 13 45 1 0 13 46 1 0 13 47 1 0 14 48 1 0 14 49 1 0 14 50 1 0 15 51 1 1 16 52 1 0 16 53 1 0 17 54 1 0 17 55 1 0 19 56 1 0 19 57 1 0 19 58 1 0 21 59 1 0 22 60 1 0 22 61 1 0 24 62 1 0 24 63 1 0 24 64 1 0 25 65 1 0 28 66 1 0 M END

Standard InCHIKey	UTSCVCXUBUMWOX-ICDOJPABSA-N
Standard InCHI	InChI=1S/C25H38O3/c1-15(21(27)28)16-9-13-25(6)18-7-8-19-22(2,3)20(26)11-12-23(19,4)17(18)10-14-24(16,25)5/h7,10,15-16,19-20,26H,8-9,11-14H2,1-6H3,(H,27,28)/t15-,16+,19-,20-,23+,24+,25-/m0/s1
SMILES	C[C@@H]([C@H]1CC[C@@]2(C)C3=CC[C@H]4C(C)(C)[C@H](CC[C@]4(C)C3=CC[C@]12C)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	386.28	Volume:	425.192 ? Van der Waals volume.
Dense:	0.908	LogP:	3.953 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.227 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.195 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	21.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.65	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.73	Fsp³:	0.8
MCE-18:	79.911 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.631	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.188 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.511	Promiscuous compounds:	0.04

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.818	MDCK Permeability:	-4.674
Pgp-inhibitor:	0.019	Pgp-substrate:	0.086
PAMPA:	0.986 ? 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%):	0.056	30% Bioavailability (F30%):	0.007
50% Bioavailability (F50%):	0.855

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.47	MRP1:	0.916
Plasma Protein Binding (PPB):	88.758%	Volume Distribution (VD):	-0.266
Fu:	10.599% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.983	BCRP inhibitor:	0.518
BSEP inhibitor:	0.945

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.005
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.259
HLM stability:	0.0 ? 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):

4.853

Half-life (T1/2):

1.327

ADMET: Toxicity

hERG Blockers:	0.033	hERG Blockers (10um):	0.063
Human Hepatotoxicity (H-HT):	0.556	Drug-induced Liver Injury (DILI):	0.189
AMES Toxicity:	0.1	Rat Oral Acute Toxicity:	0.25
Maximum Recommended Daily Dose:	0.595	Skin Sensitization:	0.806
Carcinogencity:	0.532	Eye Corrosion:	0.019
Eye Irritation:	0.791	Respiratory Toxicity:	0.72
Drug-induced Neurotoxicity:	0.034	Ototoxicity:	0.687
Hematotoxicity:	0.307	Drug-induced Nephrotoxicity:	0.629
Genotoxicity:	0.528	RPMI-8226 Immunitoxicity:	0.071
A549 Cytotoxicity:	0.052	Hek293 Cytotoxicity:	0.207
BCF:	0.665 ? 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:	3.527 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.081 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.333 ? 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
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	callus	n.a.	PMID[10552648]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18214349]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049975]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38719900]
NPO8234	Vernonia galamensis	Species	Asteraceae	Eukaryota	n.a.	seed	n.a.	PMID[9930408]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5540	Amorpha canescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8234	Vernonia galamensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8620	Caesalpinia major	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8009	Arctotis venusta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8771	Heterodermia dissecta	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4072	Anacyclus radiatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9455	Uncaria orientalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9455	Uncaria orientalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8620	Caesalpinia major	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5540	Amorpha canescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24536	Senecio cylindricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4875	Ugni molinae	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4072	Anacyclus radiatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9072	Bolocera tuediae	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8009	Arctotis venusta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6292	Teucrium brevifolium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5832	Acacia nelsonii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4321	Siphula ceratites	Species	Icmadophilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8620	Caesalpinia major	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8234	Vernonia galamensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9330	Odinia antillensis	Species	Odiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2389	Pinus japonica	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3668	Kalanchoe delagoensis	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8771	Heterodermia dissecta	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7188	Zieria granulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9455	Uncaria orientalis	Species	Rubiaceae	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 NPC140864 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	19903
0.1-0.2	25299
0.2-0.3	4089
0.3-0.4	455
0.4-0.5	72
0.5-0.6	20
0.6-0.7	15
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8103	Intermediate Similarity	NPC84271
0.8103	Intermediate Similarity	NPC102414
0.7833	Intermediate Similarity	NPC77168
0.7705	Intermediate Similarity	NPC469406
0.6825	Remote Similarity	NPC212948
0.6406	Remote Similarity	NPC222845
0.6406	Remote Similarity	NPC296577
0.6364	Remote Similarity	NPC214697
0.6333	Remote Similarity	NPC205455
0.623	Remote Similarity	NPC6707
0.6212	Remote Similarity	NPC45324
0.6212	Remote Similarity	NPC162001
0.6176	Remote Similarity	NPC141401
0.6119	Remote Similarity	NPC484975
0.6119	Remote Similarity	NPC186810
0.6119	Remote Similarity	NPC48647
0.6119	Remote Similarity	NPC321301
0.6094	Remote Similarity	NPC475772
0.6032	Remote Similarity	NPC202389
0.597	Remote Similarity	NPC203035
0.5902	Remote Similarity	NPC72507
0.5781	Remote Similarity	NPC231310
0.5735	Remote Similarity	NPC138536
0.5652	Remote Similarity	NPC477812
0.5645	Remote Similarity	NPC20853
0.5571	Remote Similarity	NPC484968
0.5429	Remote Similarity	NPC608955
0.5342	Remote Similarity	NPC39082
0.5342	Remote Similarity	NPC610107
0.5294	Remote Similarity	NPC83569
0.5294	Remote Similarity	NPC233836
0.5294	Remote Similarity	NPC159046
0.5294	Remote Similarity	NPC187376
0.5231	Remote Similarity	NPC147568
0.5205	Remote Similarity	NPC484797
0.5143	Remote Similarity	NPC69279
0.5139	Remote Similarity	NPC484967
0.5135	Remote Similarity	NPC49670
0.5075	Remote Similarity	NPC201852

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC140864 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6163
0.1-0.2	2900
0.2-0.3	85
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