NPASS Compound

Natural Product: NPC161162

Natural Product ID	NPC161162
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UJGXCOFZMJCRLN-YDDBCJSBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003569] Pregnane steroids [CHEMONTID:0001468] Gluco/mineralocorticoids, progestogins 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 64 67 0 0 0 0 0 0 0 0999 V2000 -4.9993 -1.2622 0.4369 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9920 -0.1968 -0.0993 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6849 -0.7738 0.2427 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6215 -2.1175 -0.5134 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2326 -2.1179 -1.1801 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4800 -1.3156 -0.1953 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9077 -0.9612 -0.5166 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7485 -2.2294 -0.2949 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1711 -1.9044 -0.1211 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7034 -0.7099 -0.0247 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1681 -0.5891 0.1480 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6163 0.6002 0.9210 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4571 1.2330 1.6105 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4097 1.6704 0.5756 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7949 0.4811 -0.0958 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6758 0.8128 -1.5877 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4792 0.0566 0.4392 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5438 1.1617 0.8034 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7935 0.5657 1.2013 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4229 -0.1008 -0.0322 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3574 0.7667 -1.2520 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2835 1.4701 0.0620 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4228 1.0078 0.4928 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8575 2.2349 -0.0004 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8699 1.1291 0.2884 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9571 -1.1709 -0.1017 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5799 -2.2543 0.2132 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0861 -1.1767 1.5319 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2259 -0.1637 -1.1827 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7130 -1.0546 1.3269 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3388 -2.1306 -1.3595 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6913 -2.9740 0.1551 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 -3.1481 -1.2610 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2764 -1.5908 -2.1368 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4812 -1.7961 0.8263 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0644 -0.7178 -1.5739 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5698 -2.9588 -1.1181 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4048 -2.7479 0.6369 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8500 -2.7759 -0.0685 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5358 -1.5034 0.6613 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6212 -0.6103 -0.8661 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3600 0.3152 1.7055 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8181 2.1564 2.1138 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0348 0.5098 2.3225 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9803 2.2973 -0.1525 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7202 2.3300 1.0927 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4995 1.5391 -1.8384 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8938 -0.0827 -2.2142 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7418 1.3160 -1.8308 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6813 -0.5083 1.3984 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4804 1.9661 0.0758 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9350 1.6133 1.7641 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5254 -0.2707 1.9174 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4485 1.2533 1.7183 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2052 1.8434 -1.0557 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5090 0.4911 -1.9423 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2495 0.6759 -1.9015 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6927 0.9154 -0.6462 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8233 2.2734 -1.1111 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9128 2.5474 0.4673 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5687 3.0882 0.2553 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1231 2.1826 0.5373 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4350 0.4916 0.9844 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1185 0.9188 -0.7848 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 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 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 12 22 1 0 2 23 1 0 23 24 1 0 23 25 1 0 20 3 1 0 20 6 1 0 17 7 1 0 15 10 1 0 1 26 1 0 1 27 1 0 1 28 1 0 2 29 1 6 3 30 1 1 4 31 1 0 4 32 1 0 5 33 1 0 5 34 1 0 6 35 1 1 7 36 1 6 8 37 1 0 8 38 1 0 9 39 1 0 11 40 1 0 11 41 1 0 12 42 1 1 13 43 1 0 13 44 1 0 14 45 1 0 14 46 1 0 16 47 1 0 16 48 1 0 16 49 1 0 17 50 1 1 18 51 1 0 18 52 1 0 19 53 1 0 19 54 1 0 21 55 1 0 21 56 1 0 21 57 1 0 22 58 1 0 24 59 1 0 24 60 1 0 24 61 1 0 25 62 1 0 25 63 1 0 25 64 1 0 M END

Standard InCHIKey	UJGXCOFZMJCRLN-YDDBCJSBSA-N
Standard InCHI	InChI=1S/C23H39NO/c1-15(24(4)5)19-8-9-20-18-7-6-16-14-17(25)10-12-22(16,2)21(18)11-13-23(19,20)3/h6,15,17-21,25H,7-14H2,1-5H3/t15-,17+,18+,19-,20+,21+,22+,23-/m1/s1
SMILES	C[C@H]([C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)N(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	345.3	Volume:	389.289 ? Van der Waals volume.
Dense:	0.887	LogP:	4.421 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.88 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.482 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	20.0
TPSA:	23.47 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.721	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.312	Fsp³:	0.913
MCE-18:	69.727 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.79	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? 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:	0.107	Promiscuous compounds:	0.074

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.007	MDCK Permeability:	-4.933
Pgp-inhibitor:	0.044	Pgp-substrate:	0.716
PAMPA:	0.067 ? 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%):	0.001	30% Bioavailability (F30%):	0.019
50% Bioavailability (F50%):	0.905

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.97	MRP1:	0.315
Plasma Protein Binding (PPB):	45.935%	Volume Distribution (VD):	0.219
Fu:	52.875% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.921
BSEP inhibitor:	0.172

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.309	CYP2D6-substrate:	0.006
CYP3A4-inhibitor:	0.472	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.009 ? 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):

17.576

Half-life (T1/2):

1.828

ADMET: Toxicity

hERG Blockers:	0.366	hERG Blockers (10um):	0.35
Human Hepatotoxicity (H-HT):	0.64	Drug-induced Liver Injury (DILI):	0.345
AMES Toxicity:	0.151	Rat Oral Acute Toxicity:	0.107
Maximum Recommended Daily Dose:	0.692	Skin Sensitization:	0.993
Carcinogencity:	0.893	Eye Corrosion:	0.22
Eye Irritation:	0.908	Respiratory Toxicity:	0.915
Drug-induced Neurotoxicity:	0.091	Ototoxicity:	0.459
Hematotoxicity:	0.48	Drug-induced Nephrotoxicity:	0.646
Genotoxicity:	0.307	RPMI-8226 Immunitoxicity:	0.037
A549 Cytotoxicity:	0.15	Hek293 Cytotoxicity:	0.605
BCF:	1.826 ? 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:	3.628 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.801 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.38 ? 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
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[12951092]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12951092]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[15930771]
NPO6711	Streptomyces mirabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19818612]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38999684]
NPO18213	Strychnos variabilis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12560	Cassia leptophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26605	Funtumia elastica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9527	Dendrodoa grossularia	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10366	Vincetoxicum stauntonii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26605	Funtumia elastica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12560	Cassia leptophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26605	Funtumia elastica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10366	Vincetoxicum stauntonii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10366	Vincetoxicum stauntonii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7351	Uncaria pteropoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18213	Strychnos variabilis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10911	Euphorbia peplis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10366	Vincetoxicum stauntonii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13128	Crotalaria rosenii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9527	Dendrodoa grossularia	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26674	Leucas volkensii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12560	Cassia leptophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24703	Prostanthera prunelloides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5175	Diplospora dubia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4160	Cephalosporium polyaleurum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11838	Euphorbia regis-jubae	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6711	Streptomyces mirabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26044	Melandrium firmum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26605	Funtumia elastica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2332	Plantago serraria	Species	Plantaginaceae	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 NPC161162 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	24068
0.1-0.2	23178
0.2-0.3	2273
0.3-0.4	206
0.4-0.5	72
0.5-0.6	20
0.6-0.7	38
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	Natural Product ID
0.6792	Remote Similarity	NPC162742
0.6792	Remote Similarity	NPC304309
0.6792	Remote Similarity	NPC470228
0.6667	Remote Similarity	NPC22105
0.6667	Remote Similarity	NPC221758
0.6667	Remote Similarity	NPC34019
0.6667	Remote Similarity	NPC107059
0.6667	Remote Similarity	NPC21773
0.6667	Remote Similarity	NPC600590
0.6545	Remote Similarity	NPC136188
0.6545	Remote Similarity	NPC28657
0.6545	Remote Similarity	NPC474216
0.6545	Remote Similarity	NPC154330
0.6491	Remote Similarity	NPC75810
0.6429	Remote Similarity	NPC230301
0.6429	Remote Similarity	NPC113733
0.6429	Remote Similarity	NPC198968
0.6429	Remote Similarity	NPC285893
0.6429	Remote Similarity	NPC134847
0.6316	Remote Similarity	NPC241290
0.6316	Remote Similarity	NPC164840
0.6316	Remote Similarity	NPC51014
0.6316	Remote Similarity	NPC484739
0.6316	Remote Similarity	NPC209944
0.6316	Remote Similarity	NPC264245
0.6316	Remote Similarity	NPC155986
0.6207	Remote Similarity	NPC328714
0.6207	Remote Similarity	NPC321381
0.6167	Remote Similarity	NPC243985
0.6167	Remote Similarity	NPC280710
0.6167	Remote Similarity	NPC240650
0.6102	Remote Similarity	NPC472265
0.6102	Remote Similarity	NPC318495
0.6102	Remote Similarity	NPC33913
0.6102	Remote Similarity	NPC59453
0.6066	Remote Similarity	NPC474164
0.6038	Remote Similarity	NPC96319
0.6	Remote Similarity	NPC603646
0.5965	Remote Similarity	NPC328313
0.5902	Remote Similarity	NPC473943
0.5902	Remote Similarity	NPC155011
0.5846	Remote Similarity	NPC91604
0.5806	Remote Similarity	NPC47761
0.5806	Remote Similarity	NPC488870
0.5781	Remote Similarity	NPC601043
0.5781	Remote Similarity	NPC605412
0.5574	Remote Similarity	NPC1272
0.5574	Remote Similarity	NPC470614
0.5571	Remote Similarity	NPC212874
0.5517	Remote Similarity	NPC151519
0.5484	Remote Similarity	NPC477522
0.5424	Remote Similarity	NPC20688
0.5333	Remote Similarity	NPC76879
0.5303	Remote Similarity	NPC176012
0.5161	Remote Similarity	NPC87604
0.5152	Remote Similarity	NPC474189
0.5147	Remote Similarity	NPC471083
0.5139	Remote Similarity	NPC3715

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC161162 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6941
0.1-0.2	2049
0.2-0.3	145
0.3-0.4	8
0.4-0.5	2
0.5-0.6	1
0.6-0.7	4
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
0.6667	Remote Similarity	NPD4786	Phase 1
0.6545	Remote Similarity	NPD6942	Phase 4
0.6429	Remote Similarity	NPD7339	Approved
0.6038	Remote Similarity	NPD3701	Pre-clinical
0.5517	Remote Similarity	NPD3667	Phase 4

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