NPASS Compound

Natural Product: NPC158141

Natural Product ID	NPC158141
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(4As,6Ar,6As,6Br,8Ar,9R,12Ar,14Bs)-9-(Hydroxymethyl)-2,2,6A,6B,9,12A-Hexamethyl-10-Oxo-3,4,5,6,6A,7,8,8A,11,12,13,14B-Dodecahydro-1H-Picene-4A-Carboxylic Acid
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,9R,12aR,14bS)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1797141
PubChem CID	12310388
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 80 84 0 0 0 0 0 0 0 0999 V2000 7.2250 0.6066 -0.2021 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9277 1.0572 -0.1682 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9586 -0.0485 0.2935 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4096 -0.4351 1.6566 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2036 -1.1749 -0.6830 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9003 -2.0816 -0.3239 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5515 -1.0476 -2.0046 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1012 -0.7330 -1.9272 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6209 -0.5978 -0.4614 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5631 0.4121 0.1512 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0247 1.1153 1.3631 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6434 1.6743 1.1010 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7031 0.5961 0.6703 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2417 0.0003 -0.6058 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2987 -0.9200 -1.3100 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0317 -0.9919 -0.6558 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5384 -0.0669 0.1392 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6637 1.1279 0.3619 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6375 1.9686 -0.8921 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2873 1.9356 1.4351 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7107 2.2823 1.1623 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5859 1.1150 0.7605 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8192 -0.1930 0.7998 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6638 -1.3733 0.5519 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7599 -1.2208 -0.4521 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0824 0.1349 -0.9309 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1714 1.2489 -0.5978 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0603 -1.8992 0.0243 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3788 -2.0449 -1.7004 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6612 1.0919 1.8135 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8559 1.2438 1.5366 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2707 0.8938 3.1146 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6110 -0.4041 1.7960 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6794 -1.9670 0.0865 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2874 -0.0346 -0.9714 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5800 1.5436 -1.0844 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8751 1.8291 0.6548 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0959 -1.3289 1.5592 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0711 0.3425 2.1424 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6632 -0.7047 2.3882 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7442 -2.0002 -2.5634 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1226 -0.2598 -2.5640 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9118 0.2489 -2.3957 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4722 -1.5053 -2.4313 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5850 1.2443 -0.6262 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6824 2.0296 1.4953 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0927 0.5757 2.2994 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2679 2.0824 2.0721 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7469 2.5118 0.4191 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4016 0.8691 -1.2873 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1396 -0.6578 -2.3719 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6814 -1.9765 -1.3514 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6474 -1.8556 -0.8303 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4032 2.7819 -0.8850 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3145 2.5211 -1.0332 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9338 1.3388 -1.7539 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7316 2.9182 1.4787 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2263 1.5264 2.4529 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0670 2.7767 2.1212 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8851 3.0737 0.4116 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 -0.2259 1.9182 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1214 -2.3265 0.4082 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2206 -1.6070 1.5234 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1246 0.4248 -0.5982 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2048 0.1814 -2.0644 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7791 2.2079 -0.5990 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3731 1.4229 -1.3397 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1559 -1.8224 1.1336 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9331 -1.4925 -0.5054 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0354 -2.9890 -0.1937 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2916 -2.3696 -2.2258 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9125 -2.9829 -1.2911 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6572 -1.5104 -2.3252 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8802 1.0221 3.9132 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0285 -1.2581 1.5791 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2664 0.1782 2.6965 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6016 -0.7939 2.1068 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6793 -2.4177 0.3572 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1027 -2.7466 -0.6192 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2893 -2.0904 1.0044 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 3 2 1 6 3 4 1 0 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 25 29 1 0 22 30 1 1 30 31 2 0 30 32 1 0 13 33 1 1 9 34 1 1 10 3 1 0 18 13 1 0 27 22 1 0 14 9 1 0 23 17 1 0 1 35 1 0 2 36 1 0 2 37 1 0 4 38 1 0 4 39 1 0 4 40 1 0 7 41 1 0 7 42 1 0 8 43 1 0 8 44 1 0 10 45 1 6 11 46 1 0 11 47 1 0 12 48 1 0 12 49 1 0 14 50 1 6 15 51 1 0 15 52 1 0 16 53 1 0 19 54 1 0 19 55 1 0 19 56 1 0 20 57 1 0 20 58 1 0 21 59 1 0 21 60 1 0 23 61 1 1 24 62 1 0 24 63 1 0 26 64 1 0 26 65 1 0 27 66 1 0 27 67 1 0 28 68 1 0 28 69 1 0 28 70 1 0 29 71 1 0 29 72 1 0 29 73 1 0 32 74 1 0 33 75 1 0 33 76 1 0 33 77 1 0 34 78 1 0 34 79 1 0 34 80 1 0 M END

Standard InCHIKey	WCXZTKJFWJFMJG-AOIBKUJJSA-N
Standard InCHI	InChI=1S/C30H46O4/c1-25(2)13-15-30(24(33)34)16-14-28(5)19(20(30)17-25)7-8-22-26(3)11-10-23(32)27(4,18-31)21(26)9-12-29(22,28)6/h7,20-22,31H,8-18H2,1-6H3,(H,33,34)/t20-,21+,22+,26-,27-,28+,29+,30-/m0/s1
SMILES	OC[C@]1(C)C(=O)CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(CC1)(C)C)C(=O)O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	511.905 ? Van der Waals volume.
Dense:	0.919	LogP:	3.601 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.17 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.539 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	74.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.457	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.761	Fsp³:	0.867
MCE-18:	104.464 ? 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:	0.876	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.466	Promiscuous compounds:	0.044

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.534	MDCK Permeability:	-5.051
Pgp-inhibitor:	0.006	Pgp-substrate:	0.0
PAMPA:	1.0 ? 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%):	0.058	30% Bioavailability (F30%):	0.002
50% Bioavailability (F50%):	0.934

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.648	MRP1:	0.924
Plasma Protein Binding (PPB):	93.701%	Volume Distribution (VD):	-0.282
Fu:	6.534% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.302	BCRP inhibitor:	0.232
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.248	CYP2C19-substrate:	0.017
CYP2C9-inhibitor:	0.109	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	0.846	CYP3A4-substrate:	0.014
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.055
HLM stability:	0.02 ? 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):

4.27

Half-life (T1/2):

0.714

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.03
Human Hepatotoxicity (H-HT):	0.757	Drug-induced Liver Injury (DILI):	0.484
AMES Toxicity:	0.201	Rat Oral Acute Toxicity:	0.277
Maximum Recommended Daily Dose:	0.222	Skin Sensitization:	0.898
Carcinogencity:	0.913	Eye Corrosion:	0.008
Eye Irritation:	0.337	Respiratory Toxicity:	0.601
Drug-induced Neurotoxicity:	0.048	Ototoxicity:	0.719
Hematotoxicity:	0.68	Drug-induced Nephrotoxicity:	0.872
Genotoxicity:	0.77	RPMI-8226 Immunitoxicity:	0.031
A549 Cytotoxicity:	0.055	Hek293 Cytotoxicity:	0.113
BCF:	1.031 ? 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:	3.742 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.445 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.607 ? 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
NPO12690	Caltha palustris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12690	Caltha palustris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12690	Caltha palustris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12690	Caltha palustris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12690	Caltha palustris	Species	Ranunculaceae	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
IC50	2

Activity Type	# Activity
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2681	Individual protein	Glycogen phosphorylase, muscle form	Oryctolagus cuniculus	IC50	=	53703.18	nM	PMID[21439694]
NPT2681	Individual protein	Glycogen phosphorylase, muscle form	Oryctolagus cuniculus	IC50	=	53500.0	nM	PMID[21439694]

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 NPC158141 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	19119
0.1-0.2	26042
0.2-0.3	3768
0.3-0.4	571
0.4-0.5	203
0.5-0.6	96
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
0.7424	Intermediate Similarity	NPC173089
0.7231	Intermediate Similarity	NPC480946
0.7231	Intermediate Similarity	NPC130577
0.7231	Intermediate Similarity	NPC142415
0.7231	Intermediate Similarity	NPC102683
0.7206	Intermediate Similarity	NPC148964
0.7121	Intermediate Similarity	NPC270768
0.7121	Intermediate Similarity	NPC59263
0.7121	Intermediate Similarity	NPC210106
0.7027	Intermediate Similarity	NPC476890
0.7027	Intermediate Similarity	NPC476889
0.6912	Remote Similarity	NPC291028
0.6912	Remote Similarity	NPC298554
0.6875	Remote Similarity	NPC604575
0.6765	Remote Similarity	NPC231063
0.6765	Remote Similarity	NPC282395
0.6765	Remote Similarity	NPC110308
0.6761	Remote Similarity	NPC6255
0.6667	Remote Similarity	NPC200752
0.6667	Remote Similarity	NPC120840
0.6618	Remote Similarity	NPC84319
0.6618	Remote Similarity	NPC52021
0.6618	Remote Similarity	NPC599947
0.6567	Remote Similarity	NPC267691
0.6377	Remote Similarity	NPC182797
0.6377	Remote Similarity	NPC282616
0.6377	Remote Similarity	NPC275809
0.6377	Remote Similarity	NPC37038
0.6377	Remote Similarity	NPC156981
0.6377	Remote Similarity	NPC52169
0.6377	Remote Similarity	NPC488562
0.6286	Remote Similarity	NPC106112
0.6286	Remote Similarity	NPC261935
0.6286	Remote Similarity	NPC38754
0.6286	Remote Similarity	NPC481360
0.6232	Remote Similarity	NPC198664
0.6176	Remote Similarity	NPC280654
0.6164	Remote Similarity	NPC296164
0.6143	Remote Similarity	NPC121798
0.6143	Remote Similarity	NPC234346
0.6111	Remote Similarity	NPC474963
0.6087	Remote Similarity	NPC274050
0.6087	Remote Similarity	NPC162632
0.6081	Remote Similarity	NPC96580
0.6076	Remote Similarity	NPC204407
0.6	Remote Similarity	NPC474727
0.6	Remote Similarity	NPC28198
0.6	Remote Similarity	NPC476123
0.6	Remote Similarity	NPC606107
0.5946	Remote Similarity	NPC324063
0.5921	Remote Similarity	NPC600880
0.5915	Remote Similarity	NPC307282
0.5833	Remote Similarity	NPC284807
0.5833	Remote Similarity	NPC130278
0.5833	Remote Similarity	NPC472149
0.5833	Remote Similarity	NPC473538
0.5833	Remote Similarity	NPC609452
0.5802	Remote Similarity	NPC283849
0.5783	Remote Similarity	NPC100383
0.5769	Remote Similarity	NPC93744
0.5769	Remote Similarity	NPC476888
0.5698	Remote Similarity	NPC475472
0.5694	Remote Similarity	NPC64872
0.5694	Remote Similarity	NPC25906
0.5663	Remote Similarity	NPC286347
0.5647	Remote Similarity	NPC294112
0.5641	Remote Similarity	NPC481362
0.5632	Remote Similarity	NPC22676
0.5616	Remote Similarity	NPC1753
0.5616	Remote Similarity	NPC88116
0.56	Remote Similarity	NPC471588
0.56	Remote Similarity	NPC130520
0.56	Remote Similarity	NPC481316
0.5581	Remote Similarity	NPC191410
0.5541	Remote Similarity	NPC145667
0.5541	Remote Similarity	NPC228784
0.5541	Remote Similarity	NPC324341
0.5541	Remote Similarity	NPC477288
0.5541	Remote Similarity	NPC601810
0.5529	Remote Similarity	NPC43353
0.5479	Remote Similarity	NPC32118
0.5467	Remote Similarity	NPC201657
0.5455	Remote Similarity	NPC270667
0.5455	Remote Similarity	NPC164194
0.5443	Remote Similarity	NPC188833
0.5429	Remote Similarity	NPC3915
0.5405	Remote Similarity	NPC271614
0.5393	Remote Similarity	NPC198621
0.5393	Remote Similarity	NPC216940
0.5342	Remote Similarity	NPC474806
0.5342	Remote Similarity	NPC187722
0.5342	Remote Similarity	NPC133579
0.5341	Remote Similarity	NPC171007
0.5341	Remote Similarity	NPC190849
0.5341	Remote Similarity	NPC475611
0.5333	Remote Similarity	NPC136877
0.5333	Remote Similarity	NPC12288
0.5325	Remote Similarity	NPC222047
0.5275	Remote Similarity	NPC174679
0.5275	Remote Similarity	NPC25605
0.5275	Remote Similarity	NPC279554
0.5275	Remote Similarity	NPC59804
0.527	Remote Similarity	NPC263272
0.527	Remote Similarity	NPC229281
0.527	Remote Similarity	NPC51700
0.527	Remote Similarity	NPC88716
0.527	Remote Similarity	NPC306541
0.527	Remote Similarity	NPC68160
0.527	Remote Similarity	NPC606443
0.5263	Remote Similarity	NPC193750
0.5217	Remote Similarity	NPC127056
0.5217	Remote Similarity	NPC109079
0.5205	Remote Similarity	NPC201655
0.52	Remote Similarity	NPC61543
0.52	Remote Similarity	NPC293048
0.52	Remote Similarity	NPC225585
0.52	Remote Similarity	NPC481314
0.5195	Remote Similarity	NPC608622
0.5165	Remote Similarity	NPC605663
0.5161	Remote Similarity	NPC472949
0.5161	Remote Similarity	NPC488561
0.5132	Remote Similarity	NPC202728
0.5132	Remote Similarity	NPC158059
0.5132	Remote Similarity	NPC293564
0.5132	Remote Similarity	NPC136697
0.5128	Remote Similarity	NPC488521
0.5122	Remote Similarity	NPC40918
0.5122	Remote Similarity	NPC603645
0.5114	Remote Similarity	NPC18982
0.5109	Remote Similarity	NPC132126
0.5109	Remote Similarity	NPC56713
0.5109	Remote Similarity	NPC606782
0.5106	Remote Similarity	NPC22956
0.5104	Remote Similarity	NPC180550
0.5104	Remote Similarity	NPC35405
0.5067	Remote Similarity	NPC474511
0.5065	Remote Similarity	NPC96496
0.5065	Remote Similarity	NPC191412
0.5065	Remote Similarity	NPC91010
0.5065	Remote Similarity	NPC114159
0.5065	Remote Similarity	NPC6818
0.5063	Remote Similarity	NPC481315
0.5056	Remote Similarity	NPC475627
0.5054	Remote Similarity	NPC114441
0.5053	Remote Similarity	NPC469945

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC158141 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5445
0.1-0.2	3629
0.2-0.3	67
0.3-0.4	7
0.4-0.5	1
0.5-0.6	1
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
0.5109	Remote Similarity	NPD8166	Discontinued

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