NPASS Compound

Natural Product: NPC184512

Natural Product ID	NPC184512
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Caseargrewins I
IUPAC Name	[(1S,3R,5R,6aS,7R,8R,10S,10aS)-1,3-diacetyloxy-10-hydroxy-7,8-dimethyl-7-[(2Z)-3-methylpenta-2,4-dienyl]-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] hexanoate
Synonyms	caseargrewins I
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL398225
PubChem CID	16756888
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

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 82 84 0 0 0 0 0 0 0 0999 V2000 7.6813 -2.5660 0.5613 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7098 -1.5663 1.1445 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7021 -2.2515 2.0692 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8974 -3.2988 1.3378 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0988 -2.7611 0.1826 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1039 -1.7678 0.6316 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9656 -1.5337 1.8530 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2911 -1.0581 -0.2396 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3565 -0.1258 0.1882 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6495 1.2534 -0.3412 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6718 2.1221 -0.1836 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5758 3.5621 -0.5688 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3439 3.7167 -1.9522 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1613 4.3805 -2.8294 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2059 4.9008 -2.3923 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7610 4.4493 -4.2729 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5659 4.0161 0.0880 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4439 2.9336 -0.1762 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6195 1.8017 0.4772 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0872 0.4658 0.0949 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0007 -0.4570 -0.4279 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0161 -0.2430 1.0446 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4643 -1.6485 1.3489 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3766 -0.5489 0.3882 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2105 -1.4114 -0.7881 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7379 -2.5992 -0.9597 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5809 -3.2141 0.0425 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1192 -4.4089 -0.1164 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4944 -3.3976 -2.2152 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2869 0.4095 2.3403 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1529 1.2215 2.8875 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4564 2.0918 1.9210 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8499 3.4243 2.1645 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5631 1.2099 2.4256 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5735 2.7479 -1.5543 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8035 2.8560 -2.2055 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7978 3.1334 -1.4696 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9626 2.6631 -3.6611 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6030 -2.0271 0.2566 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2151 -3.1059 -0.2825 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9922 -3.3262 1.3194 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1446 -1.0554 0.3672 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2900 -0.8639 1.7949 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3259 -2.7920 2.8411 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1272 -1.4640 2.5353 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1828 -3.7019 2.1166 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5342 -4.1574 1.0515 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7959 -2.2631 -0.5374 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6148 -3.6494 -0.2943 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3594 -0.0517 1.2662 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5517 1.5527 -0.8113 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5061 4.0464 -0.2502 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3479 5.2280 -4.8006 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3126 4.7478 -4.3785 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8809 3.4465 -4.7424 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3528 3.1681 0.3613 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7214 0.6420 -0.8384 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2318 -1.5159 -0.3738 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1845 -0.2750 -1.5332 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0234 -1.9704 2.2804 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4183 -1.6468 1.6349 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7731 -2.3873 0.5942 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7363 0.4456 -0.0198 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0875 -0.9513 1.0775 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5873 -1.0719 -1.6403 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7962 -2.7117 0.9632 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9622 -5.0077 -1.0116 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7405 -4.8311 0.6505 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9633 -4.3310 -1.8769 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4717 -3.6402 -2.6636 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8747 -2.8288 -2.9238 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4449 -0.4056 3.1280 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5945 1.8293 3.7347 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4500 0.5192 3.4300 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6386 2.0884 2.2112 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9292 3.4872 3.1674 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8391 1.7438 1.5080 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4223 0.6080 2.8239 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4356 2.0246 3.1984 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2842 1.6240 -3.9258 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7872 3.3553 -4.0018 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0668 2.9741 -4.2436 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 2 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 12 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 22 23 1 1 22 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 26 29 1 0 22 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 30 34 1 0 18 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 21 9 1 0 19 11 1 6 32 19 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 0 2 43 1 0 3 44 1 0 3 45 1 0 4 46 1 0 4 47 1 0 5 48 1 0 5 49 1 0 9 50 1 1 10 51 1 0 12 52 1 1 16 53 1 0 16 54 1 0 16 55 1 0 18 56 1 1 20 57 1 6 21 58 1 0 21 59 1 0 23 60 1 0 23 61 1 0 23 62 1 0 24 63 1 0 24 64 1 0 25 65 1 0 27 66 1 0 28 67 1 0 28 68 1 0 29 69 1 0 29 70 1 0 29 71 1 0 30 72 1 1 31 73 1 0 31 74 1 0 32 75 1 1 33 76 1 0 34 77 1 0 34 78 1 0 34 79 1 0 38 80 1 0 38 81 1 0 38 82 1 0 M END

Standard InCHIKey	OWZBTGIYKSYHIP-AHVFBGDZSA-N
Standard InCHI	InChI=1S/C30H44O8/c1-8-10-11-12-26(34)37-22-16-23-27(35-20(5)31)38-28(36-21(6)32)30(23)24(17-22)29(7,14-13-18(3)9-2)19(4)15-25(30)33/h9,13,16,19,22,24-25,27-28,33H,2,8,10-12,14-15,17H2,1,3-7H3/b18-13-/t19-,22+,24+,25+,27+,28-,29-,30-/m1/s1
SMILES	CCCCCC(=O)O[C@H]1C=C2[C@@H](OC(=O)C)O[C@H]([C@]32[C@@H](C1)[C@](C)(C/C=C(C=C)/C)[C@@H](C[C@@H]3O)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	532.3	Volume:	556.27 ? Van der Waals volume.
Dense:	0.957	LogP:	4.151 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.642 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.157 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	20.0
TPSA:	108.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.135	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.65	Fsp³:	0.7
MCE-18:	88.196 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.632	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? 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:	0.263	Promiscuous compounds:	0.647

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.165	MDCK Permeability:	-4.955
Pgp-inhibitor:	0.886	Pgp-substrate:	0.97
PAMPA:	0.63 ? 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):	0.028
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.994
Plasma Protein Binding (PPB):	95.496%	Volume Distribution (VD):	-0.331
Fu:	5.051% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.988
OATP1B3 inhibitor:	0.58	BCRP inhibitor:	0.34
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.993
CYP2C19-inhibitor:	0.602	CYP2C19-substrate:	0.5
CYP2C9-inhibitor:	0.023	CYP2C9-substrate:	0.102
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.226
CYP3A4-inhibitor:	0.037	CYP3A4-substrate:	0.595
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.99
HLM stability:	0.988 ? 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):

6.523

Half-life (T1/2):

0.71

ADMET: Toxicity

hERG Blockers:	0.102	hERG Blockers (10um):	0.564
Human Hepatotoxicity (H-HT):	0.462	Drug-induced Liver Injury (DILI):	0.872
AMES Toxicity:	0.878	Rat Oral Acute Toxicity:	0.955
Maximum Recommended Daily Dose:	0.993	Skin Sensitization:	0.994
Carcinogencity:	0.513	Eye Corrosion:	0.001
Eye Irritation:	0.083	Respiratory Toxicity:	0.97
Drug-induced Neurotoxicity:	0.842	Ototoxicity:	0.486
Hematotoxicity:	0.63	Drug-induced Nephrotoxicity:	0.854
Genotoxicity:	0.748	RPMI-8226 Immunitoxicity:	0.298
A549 Cytotoxicity:	0.849	Hek293 Cytotoxicity:	0.507
BCF:	0.99 ? 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:	4.025 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.852 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.3 ? 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
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	n.a.	bark	n.a.	PMID[15730240]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	bark	in the campus of Khon Kaen University, Khon Kaen, Thailand	2001-SEP	PMID[15730240]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17567069]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26516994]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	3

Activity Type	# Activity
Cell line	2
Non-molecular	1

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
NPT91	Cell line	KB	Homo sapiens	IC50	=	3.04	ug.mL-1	PMID[23395661]
NPT639	Cell line	NCI-H187	Homo sapiens	IC50	=	0.33	ug.mL-1	PubChem BioAssay data set
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	0.36	ug.mL-1	PMID[17567069]

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 NPC184512 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	18798
0.1-0.2	26962
0.2-0.3	3947
0.3-0.4	39
0.4-0.5	45
0.5-0.6	21
0.6-0.7	17
0.7-0.8	0
0.8-0.85	9
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC488964
0.9355	High Similarity	NPC252296
0.918	High Similarity	NPC201880
0.873	High Similarity	NPC609715
0.8689	High Similarity	NPC602188
0.8571	High Similarity	NPC134270
0.8571	High Similarity	NPC81567
0.8571	High Similarity	NPC488652
0.8281	Intermediate Similarity	NPC329623
0.8281	Intermediate Similarity	NPC609711
0.8154	Intermediate Similarity	NPC330003
0.8154	Intermediate Similarity	NPC470321
0.8154	Intermediate Similarity	NPC264867
0.8154	Intermediate Similarity	NPC473207
0.8095	Intermediate Similarity	NPC488659
0.8095	Intermediate Similarity	NPC604149
0.8	Intermediate Similarity	NPC488654
0.7727	Intermediate Similarity	NPC488660
0.7727	Intermediate Similarity	NPC488657
0.7727	Intermediate Similarity	NPC609880
0.7671	Intermediate Similarity	NPC109376
0.7612	Intermediate Similarity	NPC488658
0.7612	Intermediate Similarity	NPC488655
0.7424	Intermediate Similarity	NPC488653
0.7286	Intermediate Similarity	NPC119550
0.7206	Intermediate Similarity	NPC7644
0.7206	Intermediate Similarity	NPC479491
0.7164	Intermediate Similarity	NPC488656
0.6957	Remote Similarity	NPC316974
0.6912	Remote Similarity	NPC479943
0.6714	Remote Similarity	NPC479940
0.6714	Remote Similarity	NPC311166
0.6714	Remote Similarity	NPC479497
0.6711	Remote Similarity	NPC116292
0.6479	Remote Similarity	NPC311223
0.6389	Remote Similarity	NPC475889
0.6389	Remote Similarity	NPC7613
0.6389	Remote Similarity	NPC479942
0.6301	Remote Similarity	NPC479941
0.6267	Remote Similarity	NPC127933
0.6164	Remote Similarity	NPC217921
0.6164	Remote Similarity	NPC135015
0.6118	Remote Similarity	NPC320734
0.6098	Remote Similarity	NPC224660
0.6056	Remote Similarity	NPC88507
0.5946	Remote Similarity	NPC238397
0.5942	Remote Similarity	NPC603601
0.5926	Remote Similarity	NPC316708
0.5915	Remote Similarity	NPC600724
0.5789	Remote Similarity	NPC471363
0.5775	Remote Similarity	NPC606965
0.5733	Remote Similarity	NPC88013
0.5616	Remote Similarity	NPC488235
0.56	Remote Similarity	NPC128795
0.5542	Remote Similarity	NPC486751
0.5507	Remote Similarity	NPC604446
0.5467	Remote Similarity	NPC473204
0.5301	Remote Similarity	NPC87630
0.525	Remote Similarity	NPC40728
0.5238	Remote Similarity	NPC172867
0.5238	Remote Similarity	NPC470024
0.5125	Remote Similarity	NPC488221
0.5125	Remote Similarity	NPC488220
0.5125	Remote Similarity	NPC488216
0.5059	Remote Similarity	NPC162569
0.5059	Remote Similarity	NPC35160

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC184512 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6955
0.1-0.2	2131
0.2-0.3	64
0.3-0.4	0
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