NPASS Compound

Natural Product: NPC214756

Natural Product ID	NPC214756
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Methyl 11-Oxo-Oleanoloate
IUPAC Name	methyl (4aS,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3109256
PubChem CID	21723770
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 83 87 0 0 0 0 0 0 0 0999 V2000 -4.9214 0.9617 -3.3586 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3823 1.0965 -1.9218 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4398 2.5850 -1.6447 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3774 0.3465 -1.0627 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8911 0.5504 0.3581 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6214 -0.2879 0.5885 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9339 0.3297 1.7640 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5015 -0.0060 1.9482 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6802 0.1926 0.6529 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8139 1.6773 0.4803 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3845 -0.6141 -0.3395 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7588 -1.5054 -1.0683 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6614 -1.7235 -0.9186 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1279 -2.8393 -1.2474 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4119 -0.5757 -0.3827 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8906 -0.6813 -0.4492 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5557 -1.8375 0.1591 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1821 -0.7098 -1.9609 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6031 -0.5395 -2.3118 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4106 0.4185 -1.5385 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8483 0.9446 -0.2770 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9582 2.4880 -0.3443 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7412 0.6041 0.9161 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4366 0.6551 0.0009 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0219 0.7961 1.4318 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5004 1.0366 1.3971 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7611 -0.1903 0.9080 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8677 -1.3302 1.8975 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6454 -0.2122 -1.2348 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8428 -0.4740 -0.6341 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0427 0.4959 -1.7654 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1406 -1.5959 1.0618 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3678 -1.7669 1.1753 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3173 -2.6602 1.3916 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8743 -3.8871 1.8388 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9137 1.4077 -3.4025 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8722 -0.0836 -3.7013 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2379 1.5745 -3.9833 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6609 2.8269 -0.8963 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1287 3.1131 -2.5883 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4490 2.9201 -1.3428 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3802 0.8086 -1.1219 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3536 -0.7129 -1.3672 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6576 0.3491 1.1040 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5894 1.6132 0.4530 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4312 -0.0500 2.7178 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1798 1.4107 1.8360 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1086 0.7266 2.6862 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4159 -1.0580 2.2886 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8745 1.9880 0.4495 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3246 2.1224 -0.3610 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4197 2.1424 1.4055 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3137 -2.1223 -1.8240 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1829 0.3028 -1.0716 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4161 -2.1429 -0.5123 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9210 -2.7185 0.1999 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0894 -1.6336 1.1186 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5442 0.0850 -2.4470 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8146 -1.6654 -2.3372 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0705 -1.5719 -2.3445 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6034 -0.2740 -3.4174 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7387 1.2474 -2.2390 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9985 2.9238 0.6582 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0280 2.8412 -0.8320 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7927 2.7755 -0.9984 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1265 -0.4302 0.8818 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2074 0.7654 1.8720 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6153 1.3172 0.9156 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8184 1.4096 -0.5784 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4365 1.7682 1.7987 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2930 -0.0227 2.0854 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4034 1.8049 0.6033 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1471 1.3649 2.3953 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5045 -1.0526 2.9094 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9196 -1.6240 2.0678 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2021 -2.1553 1.5779 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5401 -1.1566 -1.0236 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2134 -1.4506 -1.0943 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8168 -0.0154 -2.7575 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2654 1.3166 -1.7927 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3659 -3.8036 2.8151 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6772 -4.2356 1.1241 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0963 -4.6883 1.8088 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 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 9 10 1 6 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 1 16 18 1 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 27 28 1 1 20 29 1 0 11 30 1 0 30 31 1 0 6 32 1 1 32 33 2 0 32 34 1 0 34 35 1 0 31 2 1 0 30 6 1 0 27 9 1 0 27 15 1 0 24 16 1 0 1 36 1 0 1 37 1 0 1 38 1 0 3 39 1 0 3 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 5 44 1 0 5 45 1 0 7 46 1 0 7 47 1 0 8 48 1 0 8 49 1 0 10 50 1 0 10 51 1 0 10 52 1 0 12 53 1 0 15 54 1 6 17 55 1 0 17 56 1 0 17 57 1 0 18 58 1 0 18 59 1 0 19 60 1 0 19 61 1 0 20 62 1 6 22 63 1 0 22 64 1 0 22 65 1 0 23 66 1 0 23 67 1 0 23 68 1 0 24 69 1 6 25 70 1 0 25 71 1 0 26 72 1 0 26 73 1 0 28 74 1 0 28 75 1 0 28 76 1 0 29 77 1 0 30 78 1 6 31 79 1 0 31 80 1 0 35 81 1 0 35 82 1 0 35 83 1 0 M END

Standard InCHIKey	WWQDFVOIJWUDSM-CYVYTNFQSA-N
Standard InCHI	InChI=1S/C31H48O4/c1-26(2)13-15-31(25(34)35-8)16-14-29(6)19(20(31)18-26)17-21(32)24-28(5)11-10-23(33)27(3,4)22(28)9-12-30(24,29)7/h17,20,22-24,33H,9-16,18H2,1-8H3/t20-,22-,23-,24+,28-,29+,30+,31-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC(=O)[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]2C1)C(=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	484.36	Volume:	529.201 ? Van der Waals volume.
Dense:	0.915	LogP:	3.543 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.505 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.789 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	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:	0.431	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.678	Fsp³:	0.871
MCE-18:	106.207 ? 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:	0.65	Fluc inhibitor:	0.019 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.1 ? 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:	0.321	Promiscuous compounds:	0.33

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.293	MDCK Permeability:	-4.981
Pgp-inhibitor:	0.738	Pgp-substrate:	0.085
PAMPA:	0.96 ? 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):	0.012
20% Bioavailability (F20%):	0.832	30% Bioavailability (F30%):	0.699
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.844	MRP1:	0.915
Plasma Protein Binding (PPB):	96.871%	Volume Distribution (VD):	0.058
Fu:	4.024% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.741
BSEP inhibitor:	0.988

ADMET: Metabolism

CYP1A2-inhibitor:	0.004	CYP1A2-substrate:	0.758
CYP2C19-inhibitor:	0.998	CYP2C19-substrate:	0.989
CYP2C9-inhibitor:	0.011	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.008
CYP3A4-inhibitor:	0.546	CYP3A4-substrate:	0.949
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.676
HLM stability:	0.789 ? 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):

8.581

Half-life (T1/2):

0.448

ADMET: Toxicity

hERG Blockers:	0.107	hERG Blockers (10um):	0.237
Human Hepatotoxicity (H-HT):	0.842	Drug-induced Liver Injury (DILI):	0.42
AMES Toxicity:	0.359	Rat Oral Acute Toxicity:	0.551
Maximum Recommended Daily Dose:	0.761	Skin Sensitization:	0.902
Carcinogencity:	0.886	Eye Corrosion:	0.021
Eye Irritation:	0.655	Respiratory Toxicity:	0.934
Drug-induced Neurotoxicity:	0.157	Ototoxicity:	0.433
Hematotoxicity:	0.449	Drug-induced Nephrotoxicity:	0.8
Genotoxicity:	0.667	RPMI-8226 Immunitoxicity:	0.055
A549 Cytotoxicity:	0.371	Hek293 Cytotoxicity:	0.336
BCF:	2.15 ? 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:	4.547 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.95 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.45 ? 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
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	Palauan	n.a.	PMID[12350142]
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	Indo-Pacific	n.a.	PMID[15387674]
NPO2543	Anthopleura pacifica	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28655	Perovskia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13905	Galaxaura filamentosa	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22067	Pogostemon stellatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2543	Anthopleura pacifica	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13905	Galaxaura filamentosa	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28655	Perovskia angustifolia	Species	Lamiaceae	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
Ki	1
Activity	5
IC50	7
EC50	3

Activity Type	# Activity
Individual protein	1
Cell line	13
Non-molecular	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1218	Individual protein	Carbonic anhydrase II	Bos taurus	Ki	>	50000.0	nM	PMID[25147151]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell line	A2780	Homo sapiens	Activity	=	34.13	%	PMID[24361521]
NPT179	Cell line	A2780	Homo sapiens	Activity	=	33.08	%	PMID[24361521]
NPT179	Cell line	A2780	Homo sapiens	Activity	=	29.68	%	PMID[24361521]
NPT179	Cell line	A2780	Homo sapiens	Activity	=	3.11	%	PMID[24361521]
NPT179	Cell line	A2780	Homo sapiens	Activity	>	50.0	%	PMID[24361521]
NPT886	Cell line	NIH3T3	Mus musculus	IC50	=	24800.0	nM	PMID[24361521]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	21300.0	nM	PMID[24361521]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	18500.0	nM	PMID[24361521]
NPT81	Cell line	A549	Homo sapiens	IC50	=	15100.0	nM	PMID[24361521]
NPT179	Cell line	A2780	Homo sapiens	IC50	=	6600.0	nM	PMID[24361521]
NPT1215	Cell line	8505C	Homo sapiens	IC50	=	13000.0	nM	PMID[24361521]
NPT139	Cell line	HT-29	Homo sapiens	EC50	=	27620.0	nM	PMID[26177446]
NPT83	Cell line	MCF7	Homo sapiens	EC50	=	28690.0	nM	PMID[26177446]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	15600.0	nM	PMID[24361521]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	>	30000.0	nM	PMID[26177446]

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 NPC214756 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	17282
0.1-0.2	26782
0.2-0.3	4992
0.3-0.4	689
0.4-0.5	86
0.5-0.6	14
0.6-0.7	8
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
0.746	Intermediate Similarity	NPC295643
0.7188	Intermediate Similarity	NPC272075
0.7143	Intermediate Similarity	NPC246708
0.6308	Remote Similarity	NPC602872
0.6143	Remote Similarity	NPC98874
0.6111	Remote Similarity	NPC471966
0.6056	Remote Similarity	NPC4036
0.6056	Remote Similarity	NPC65120
0.6056	Remote Similarity	NPC145067
0.6056	Remote Similarity	NPC233455
0.6056	Remote Similarity	NPC158030
0.5821	Remote Similarity	NPC470588
0.5797	Remote Similarity	NPC479748
0.5735	Remote Similarity	NPC480944
0.5714	Remote Similarity	NPC136313
0.5692	Remote Similarity	NPC190035
0.5634	Remote Similarity	NPC488519
0.5441	Remote Similarity	NPC235341
0.5405	Remote Similarity	NPC610635
0.5375	Remote Similarity	NPC167383
0.5303	Remote Similarity	NPC290598
0.5303	Remote Similarity	NPC30590
0.5286	Remote Similarity	NPC267517
0.5211	Remote Similarity	NPC40552
0.5072	Remote Similarity	NPC101475

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC214756 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6768
0.1-0.2	2264
0.2-0.3	109
0.3-0.4	5
0.4-0.5	3
0.5-0.6	0
0.6-0.7	1
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
0.6056	Remote Similarity	NPD7515	Phase 2

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