NPASS Compound

Natural Product: NPC7644

Natural Product ID	NPC7644
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Caseanigrescen D
IUPAC Name	[(1S,3R,5R,6aS,7R,8R,10S,10aS)-1,3-diacetyloxy-10-hydroxy-7,8-dimethyl-7-(3-methylidenepent-4-enyl)-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] butanoate
Synonyms	Caseanigrescen D
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL220967
PubChem CID	16109795
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 76 78 0 0 0 0 0 0 0 0999 V2000 3.5372 4.6861 -3.0644 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7415 4.0244 -2.4408 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3488 3.3438 -1.1496 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3372 2.3034 -1.4608 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9609 2.0629 -2.6311 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7385 1.5267 -0.4722 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7595 0.5249 -0.7754 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3368 -0.7767 -0.4290 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5895 -1.7822 -0.1075 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8510 -3.1908 0.2846 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6181 -3.3563 1.4277 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6807 -4.1797 1.6283 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0483 -4.8987 0.6938 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3406 -4.1722 2.9580 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5818 -3.7212 0.6549 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1000 -2.5950 1.1158 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1104 -1.6574 -0.0892 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4469 -0.3166 0.1361 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4900 0.8355 -0.0399 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7706 -0.0087 -0.5636 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5698 0.7013 -1.8920 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5207 1.0284 0.2997 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8123 1.3996 -0.3127 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6441 2.3603 0.4338 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7870 1.8621 0.9611 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3925 3.7625 0.6552 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3406 4.3732 0.1785 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6515 -1.1741 -0.7918 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6363 -1.5355 0.2660 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9515 -2.4341 -1.2351 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4707 -2.3522 -1.3004 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0231 -3.6536 -1.4026 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6454 -2.1258 2.2249 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0024 -2.0643 3.4502 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2056 -2.4245 3.5138 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7277 -1.5733 4.6765 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6609 5.7862 -2.8858 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6231 4.3329 -2.5585 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4442 4.4854 -4.1503 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5686 4.7597 -2.2839 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1479 3.3039 -3.1818 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8783 4.0720 -0.4563 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2453 2.8617 -0.7112 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6460 0.5540 -1.8779 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4359 -0.8647 -0.4575 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2254 -3.8260 -0.5233 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3358 -3.7030 2.9079 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4088 -5.2309 3.3266 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7331 -3.5876 3.6942 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1156 -2.8680 1.3079 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7397 -0.2850 1.2359 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8055 1.3022 0.9272 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0120 1.6398 -0.6081 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6627 0.4412 -2.4211 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6091 1.8052 -1.8199 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4149 0.4369 -2.5985 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5468 0.7095 1.3572 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8462 1.9022 0.2906 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4300 0.5551 -0.6915 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5511 1.9513 -1.2773 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4120 2.5345 1.5098 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0507 0.8236 0.8272 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1275 4.3639 1.2583 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6112 3.8784 -0.4005 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2046 5.4262 0.3897 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3026 -0.9012 -1.6887 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3633 -2.5463 0.6962 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7308 -0.8777 1.1198 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6758 -1.7505 -0.1440 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3058 -2.8168 -2.2256 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1929 -3.2860 -0.5309 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1047 -1.8718 -2.2559 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0952 -4.0343 -2.2979 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9703 -0.4809 4.5416 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1183 -1.6984 5.5729 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6933 -2.0991 4.7320 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 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 10 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 2 0 20 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 31 32 1 0 16 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 19 7 1 0 17 9 1 6 31 17 1 0 1 37 1 0 1 38 1 0 1 39 1 0 2 40 1 0 2 41 1 0 3 42 1 0 3 43 1 0 7 44 1 6 8 45 1 0 10 46 1 6 14 47 1 0 14 48 1 0 14 49 1 0 16 50 1 1 18 51 1 1 19 52 1 0 19 53 1 0 21 54 1 0 21 55 1 0 21 56 1 0 22 57 1 0 22 58 1 0 23 59 1 0 23 60 1 0 25 61 1 0 25 62 1 0 26 63 1 0 27 64 1 0 27 65 1 0 28 66 1 6 29 67 1 0 29 68 1 0 29 69 1 0 30 70 1 0 30 71 1 0 31 72 1 6 32 73 1 0 36 74 1 0 36 75 1 0 36 76 1 0 M END

Standard InCHIKey	OYLJTRVIXSOCPW-MGZSJDQHSA-N
Standard InCHI	InChI=1S/C28H40O8/c1-8-10-24(32)35-20-14-21-25(33-18(5)29)36-26(34-19(6)30)28(21)22(15-20)27(7,12-11-16(3)9-2)17(4)13-23(28)31/h9,14,17,20,22-23,25-26,31H,2-3,8,10-13,15H2,1,4-7H3/t17-,20+,22+,23+,25+,26-,27-,28-/m1/s1
SMILES	CCCC(=O)O[C@H]1C=C2[C@@H](OC(=O)C)O[C@H]([C@]32[C@@H](C1)[C@](C)(CCC(=C)C=C)[C@H](C)C[C@@H]3O)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	504.27	Volume:	521.678 ? Van der Waals volume.
Dense:	0.967	LogP:	3.414 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.244 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.936 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	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:	0.213	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.71	Fsp³:	0.679
MCE-18:	89.064 ? 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:	0.554	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? 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:	0.288	Promiscuous compounds:	0.665

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.889	MDCK Permeability:	-4.809
Pgp-inhibitor:	0.98	Pgp-substrate:	0.939
PAMPA:	0.499 ? 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):	0.042
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015	MRP1:	0.958
Plasma Protein Binding (PPB):	87.818%	Volume Distribution (VD):	-0.245
Fu:	10.915% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.96	BCRP inhibitor:	0.762
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.953
CYP2C19-inhibitor:	0.747	CYP2C19-substrate:	0.106
CYP2C9-inhibitor:	0.005	CYP2C9-substrate:	0.121
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.037	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.902
HLM stability:	0.998 ? 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):

7.313

Half-life (T1/2):

0.941

ADMET: Toxicity

hERG Blockers:	0.064	hERG Blockers (10um):	0.43
Human Hepatotoxicity (H-HT):	0.397	Drug-induced Liver Injury (DILI):	0.599
AMES Toxicity:	0.891	Rat Oral Acute Toxicity:	0.944
Maximum Recommended Daily Dose:	0.989	Skin Sensitization:	0.981
Carcinogencity:	0.684	Eye Corrosion:	0.0
Eye Irritation:	0.065	Respiratory Toxicity:	0.931
Drug-induced Neurotoxicity:	0.746	Ototoxicity:	0.502
Hematotoxicity:	0.663	Drug-induced Nephrotoxicity:	0.808
Genotoxicity:	0.955	RPMI-8226 Immunitoxicity:	0.299
A549 Cytotoxicity:	0.61	Hek293 Cytotoxicity:	0.403
BCF:	0.693 ? 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:	3.657 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.576 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.854 ? 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]
NPO31135	Casearia nigrescens	Species	Salicaceae	Eukaryota	n.a.	flower	n.a.	PMID[17315961]
NPO31135	Casearia nigrescens	Species	Salicaceae	Eukaryota	leaves and flowers	Zahamena region of Madagascar, Toamasina, 3 km northeast of Nosivola (1741'01?S, 4838'28?)	2001-NOV	PMID[17315961]
NPO31135	Casearia nigrescens	Species	Salicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17315961]
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]
NPO31135	Casearia nigrescens	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
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	5

Activity Type	# Activity
Cell line	5

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
NPT179	Cell line	A2780	Homo sapiens	IC50	=	1000.0	nM	PMID[17315961]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	800.0	nM	PMID[26516994]
NPT1034	Cell line	Lu1	Homo sapiens	IC50	=	900.0	nM	PMID[26516994]
NPT91	Cell line	KB	Homo sapiens	IC50	=	500.0	nM	PMID[26516994]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	300.0	nM	PMID[26516994]

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 NPC7644 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	18717
0.1-0.2	26397
0.2-0.3	4578
0.3-0.4	43
0.4-0.5	28
0.5-0.6	34
0.6-0.7	33
0.7-0.8	0
0.8-0.85	1
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.931	High Similarity	NPC479943
0.9	High Similarity	NPC479940
0.8594	High Similarity	NPC127933
0.8548	High Similarity	NPC475889
0.8548	High Similarity	NPC7613
0.8548	High Similarity	NPC479942
0.8413	Intermediate Similarity	NPC479941
0.7969	Intermediate Similarity	NPC238397
0.7812	Intermediate Similarity	NPC201880
0.7727	Intermediate Similarity	NPC471363
0.7692	Intermediate Similarity	NPC217921
0.7692	Intermediate Similarity	NPC88013
0.7692	Intermediate Similarity	NPC135015
0.7424	Intermediate Similarity	NPC609715
0.7273	Intermediate Similarity	NPC134270
0.726	Intermediate Similarity	NPC486751
0.7206	Intermediate Similarity	NPC488964
0.7206	Intermediate Similarity	NPC184512
0.7077	Intermediate Similarity	NPC602188
0.7015	Intermediate Similarity	NPC479497
0.7015	Intermediate Similarity	NPC81567
0.7015	Intermediate Similarity	NPC488652
0.6986	Remote Similarity	NPC87630
0.6765	Remote Similarity	NPC128795
0.6765	Remote Similarity	NPC329623
0.6765	Remote Similarity	NPC609711
0.6714	Remote Similarity	NPC252296
0.6667	Remote Similarity	NPC330003
0.6667	Remote Similarity	NPC470321
0.6667	Remote Similarity	NPC264867
0.6667	Remote Similarity	NPC473207
0.662	Remote Similarity	NPC125423
0.6571	Remote Similarity	NPC48548
0.6567	Remote Similarity	NPC479935
0.6567	Remote Similarity	NPC488659
0.6567	Remote Similarity	NPC481019
0.6567	Remote Similarity	NPC604149
0.6533	Remote Similarity	NPC179128
0.6528	Remote Similarity	NPC40728
0.6522	Remote Similarity	NPC488654
0.6522	Remote Similarity	NPC479491
0.6308	Remote Similarity	NPC476802
0.6286	Remote Similarity	NPC488660
0.6286	Remote Similarity	NPC481017
0.6286	Remote Similarity	NPC488657
0.6286	Remote Similarity	NPC609880
0.6232	Remote Similarity	NPC472186
0.6197	Remote Similarity	NPC473545
0.6197	Remote Similarity	NPC488658
0.6197	Remote Similarity	NPC488655
0.6176	Remote Similarity	NPC479934
0.6176	Remote Similarity	NPC481020
0.6143	Remote Similarity	NPC488649
0.6029	Remote Similarity	NPC171598
0.6	Remote Similarity	NPC488653
0.5949	Remote Similarity	NPC109376
0.5926	Remote Similarity	NPC224660
0.5857	Remote Similarity	NPC479936
0.5857	Remote Similarity	NPC318917
0.5811	Remote Similarity	NPC472187
0.5797	Remote Similarity	NPC481018
0.5775	Remote Similarity	NPC488656
0.5775	Remote Similarity	NPC488236
0.5733	Remote Similarity	NPC488221
0.5733	Remote Similarity	NPC488220
0.5733	Remote Similarity	NPC488216
0.5694	Remote Similarity	NPC471366
0.5694	Remote Similarity	NPC476800
0.5694	Remote Similarity	NPC488237
0.5652	Remote Similarity	NPC472189
0.5634	Remote Similarity	NPC479939
0.5556	Remote Similarity	NPC479937
0.55	Remote Similarity	NPC116292
0.5479	Remote Similarity	NPC479938
0.5443	Remote Similarity	NPC486752
0.5417	Remote Similarity	NPC471362
0.5417	Remote Similarity	NPC471372
0.5405	Remote Similarity	NPC311223
0.5405	Remote Similarity	NPC316974
0.5349	Remote Similarity	NPC481026
0.5342	Remote Similarity	NPC472188
0.5325	Remote Similarity	NPC119550
0.5286	Remote Similarity	NPC89171
0.5278	Remote Similarity	NPC488651
0.5278	Remote Similarity	NPC488648
0.5263	Remote Similarity	NPC488963
0.5205	Remote Similarity	NPC88507
0.5114	Remote Similarity	NPC481025
0.5056	Remote Similarity	NPC320734

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC7644 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7084
0.1-0.2	1988
0.2-0.3	78
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