NPASS Compound

Natural Product: NPC473204

Natural Product ID	NPC473204
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(5R,6As,7R,8R,10S,10As)-1,3-Diacetyloxy-10-Methoxy-7,8-Dimethyl-7-[(2E)-3-Methylpenta-2,4-Dienyl]-1,3,5,6,6A,8,9,10-Octahydrobenzo[D][2]Benzofuran-5-Yl] 2-Methylbutanoate
IUPAC Name	[(5R,6aS,7R,8R,10S,10aS)-1,3-diacetyloxy-10-methoxy-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dienyl]-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] 2-methylbutanoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL364286
PubChem CID	11613467
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 5.4182 4.2854 -1.5382 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6965 3.7386 -0.3358 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8013 2.5551 -0.7302 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7209 1.5195 -1.3127 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1477 2.0765 0.5104 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3786 2.6102 1.6394 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2344 1.0146 0.5499 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6292 0.5785 1.7157 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0770 0.7485 1.6717 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3350 -0.0191 0.4570 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5256 0.5270 -0.2757 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9784 -0.4198 -1.3333 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0401 -1.4459 -1.7932 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0613 -1.9186 -0.8932 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2036 -1.4784 0.5399 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2032 -2.3511 1.1609 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5204 -3.3738 1.8952 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8157 -3.2864 1.5189 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9599 -1.7945 1.4600 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7594 -0.9029 1.9693 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6446 -3.8269 2.5464 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5731 -4.7822 2.1627 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6640 -5.1410 0.9604 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4983 -5.4270 3.1289 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8493 -3.1374 0.1424 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2120 -3.3919 0.1522 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8751 -2.9010 1.1016 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8894 -4.2022 -0.8941 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2093 -1.2400 -1.3135 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2127 -2.0510 -1.7755 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3536 0.4190 -2.5734 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1276 1.8496 -0.9531 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6094 0.9203 0.7097 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7940 1.4666 0.0348 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2859 2.6572 0.2240 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5061 3.0966 -0.5316 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6924 3.5944 1.1559 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2330 4.7931 1.3105 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7628 4.1954 -2.4181 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3389 3.6739 -1.6735 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6799 5.3627 -1.3381 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3866 3.4365 0.4754 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0294 4.5409 0.0718 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0238 2.8886 -1.4258 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1746 0.6221 -1.6208 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4859 1.2658 -0.5523 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2682 2.0034 -2.1476 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9596 1.1525 2.5772 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2698 0.2380 2.5947 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1829 1.8022 1.6547 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5255 0.2647 -0.2942 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9992 -0.8619 -1.0685 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6466 -2.3674 -2.0530 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6179 -1.1514 -2.8020 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2469 -2.9907 -1.0200 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8948 -1.9442 1.8965 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0347 -3.7107 0.5498 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5713 -1.2103 2.6137 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4184 -4.8940 4.0994 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5363 -5.3121 2.7343 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1899 -6.4879 3.2104 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0942 -4.4879 -1.6290 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7177 -3.6524 -1.3841 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2642 -5.1484 -0.4698 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1094 -1.4558 -2.1173 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5644 -2.6900 -0.9160 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8853 -2.7024 -2.6094 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6779 1.4243 -2.3198 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1918 -0.0733 -3.1040 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4895 0.4097 -3.2706 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2767 2.2525 -0.3241 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9125 2.5986 -0.8764 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6932 1.7046 -1.9443 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9899 0.0071 1.2680 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2090 1.5577 1.5156 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3057 0.8114 -0.6866 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2198 3.4478 0.2155 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1899 3.9063 -1.2064 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8926 2.2640 -1.1681 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8266 3.3908 1.7461 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8036 5.4883 1.9932 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0938 5.0719 0.7593 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 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 1 0 17 18 1 0 18 19 1 0 19 20 2 0 18 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 16 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 14 29 1 0 29 30 1 0 12 31 1 0 11 32 1 0 11 33 1 0 33 34 1 0 34 35 2 3 35 36 1 0 35 37 1 0 37 38 2 0 20 8 1 0 15 10 1 0 19 15 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 4 45 1 0 4 46 1 0 4 47 1 0 8 48 1 0 9 49 1 0 9 50 1 0 10 51 1 0 12 52 1 0 13 53 1 0 13 54 1 0 14 55 1 0 16 56 1 0 18 57 1 0 20 58 1 0 24 59 1 0 24 60 1 0 24 61 1 0 28 62 1 0 28 63 1 0 28 64 1 0 30 65 1 0 30 66 1 0 30 67 1 0 31 68 1 0 31 69 1 0 31 70 1 0 32 71 1 0 32 72 1 0 32 73 1 0 33 74 1 0 33 75 1 0 34 76 1 0 36 77 1 0 36 78 1 0 36 79 1 0 37 80 1 0 38 81 1 0 38 82 1 0 M END

Standard InCHIKey	UWFRYHUOYRQHCP-YOSDBVPHSA-N
Standard InCHI	InChI=1S/C30H44O8/c1-10-17(3)12-13-29(8)19(5)14-25(34-9)30-23(27(35-20(6)31)38-28(30)36-21(7)32)15-22(16-24(29)30)37-26(33)18(4)11-2/h10,12,15,18-19,22,24-25,27-28H,1,11,13-14,16H2,2-9H3/b17-12+/t18?,19-,22+,24+,25+,27?,28?,29-,30-/m1/s1
SMILES	CCC(C)C(=O)OC1CC2C(C(CC(C23C(OC(C3=C1)OC(=O)C)OC(=O)C)OC)C)(C)CC=C(C)C=C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	532.3	Volume:	556.27 ? Van der Waals volume.
Dense:	0.957	LogP:	4.224 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.699 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.43 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	20.0
TPSA:	97.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.171	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.844	Fsp³:	0.7
MCE-18:	91.588 ? 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:	0.118	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.326 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.357	Promiscuous compounds:	0.004

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.971	MDCK Permeability:	-4.638
Pgp-inhibitor:	0.325	Pgp-substrate:	0.522
PAMPA:	0.125 ? 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):	0.016
20% Bioavailability (F20%):	0.824	30% Bioavailability (F30%):	0.962
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.421	MRP1:	1.0
Plasma Protein Binding (PPB):	68.31%	Volume Distribution (VD):	0.086
Fu:	32.945% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.201
OATP1B3 inhibitor:	0.486	BCRP inhibitor:	0.098
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.004	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.907	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.039
CYP3A4-inhibitor:	0.19	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.54	CYP2C8-inhibitor:	0.989
HLM stability:	0.996 ? 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):

9.48

Half-life (T1/2):

0.623

ADMET: Toxicity

hERG Blockers:	0.091	hERG Blockers (10um):	0.508
Human Hepatotoxicity (H-HT):	0.646	Drug-induced Liver Injury (DILI):	0.651
AMES Toxicity:	0.726	Rat Oral Acute Toxicity:	0.696
Maximum Recommended Daily Dose:	0.951	Skin Sensitization:	0.818
Carcinogencity:	0.362	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.112
Drug-induced Neurotoxicity:	0.942	Ototoxicity:	0.849
Hematotoxicity:	0.218	Drug-induced Nephrotoxicity:	0.618
Genotoxicity:	0.874	RPMI-8226 Immunitoxicity:	0.218
A549 Cytotoxicity:	0.25	Hek293 Cytotoxicity:	0.588
BCF:	0.814 ? 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:	3.902 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.892 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.074 ? 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
NPO1241	Laetia procera	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16168652]
NPO1241	Laetia procera	Species	Salicaceae	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
Activity	5
Ratio	1

Activity Type	# Activity
Cell line	2
Organism	4

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
NPT83	Cell line	MCF7	Homo sapiens	Activity	=	4.38	uM	PMID[21456549]
NPT83	Cell line	MCF7	Homo sapiens	Ratio	=	6.8	n.a.	PMID[21456549]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	0.58	uM	PMID[21456549]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	0.66	uM	PMID[21456549]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	Activity	=	47.4	uM	PMID[21456549]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	Activity	=	10.9	uM	PMID[21456549]

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 NPC473204 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	22896
0.1-0.2	25577
0.2-0.3	1251
0.3-0.4	18
0.4-0.5	47
0.5-0.6	33
0.6-0.7	20
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9298	High Similarity	NPC488235
0.8947	High Similarity	NPC606965
0.8793	High Similarity	NPC600724
0.8276	Intermediate Similarity	NPC603601
0.7778	Intermediate Similarity	NPC471366
0.7778	Intermediate Similarity	NPC476800
0.7778	Intermediate Similarity	NPC488237
0.7571	Intermediate Similarity	NPC473216
0.7344	Intermediate Similarity	NPC472188
0.7344	Intermediate Similarity	NPC488236
0.7083	Intermediate Similarity	NPC473399
0.7059	Intermediate Similarity	NPC472187
0.7015	Intermediate Similarity	NPC473545
0.6875	Remote Similarity	NPC171598
0.6667	Remote Similarity	NPC318917
0.6667	Remote Similarity	NPC481019
0.6533	Remote Similarity	NPC162569
0.6533	Remote Similarity	NPC35160
0.6522	Remote Similarity	NPC330003
0.6522	Remote Similarity	NPC470321
0.6522	Remote Similarity	NPC264867
0.6522	Remote Similarity	NPC473207
0.6462	Remote Similarity	NPC472189
0.6364	Remote Similarity	NPC481018
0.6324	Remote Similarity	NPC472186
0.6286	Remote Similarity	NPC488658
0.6286	Remote Similarity	NPC488655
0.6269	Remote Similarity	NPC481020
0.6232	Remote Similarity	NPC488649
0.6176	Remote Similarity	NPC471362
0.6176	Remote Similarity	NPC471372
0.6154	Remote Similarity	NPC470297
0.6143	Remote Similarity	NPC481017
0.5942	Remote Similarity	NPC88507
0.5915	Remote Similarity	NPC329623
0.5714	Remote Similarity	NPC602188
0.5694	Remote Similarity	NPC201880
0.5694	Remote Similarity	NPC311166
0.5694	Remote Similarity	NPC488660
0.5694	Remote Similarity	NPC488657
0.5694	Remote Similarity	NPC81567
0.5694	Remote Similarity	NPC488652
0.5493	Remote Similarity	NPC488659
0.5493	Remote Similarity	NPC604149
0.5479	Remote Similarity	NPC311223
0.5479	Remote Similarity	NPC316974
0.5479	Remote Similarity	NPC134270
0.5479	Remote Similarity	NPC488654
0.5479	Remote Similarity	NPC609711
0.5476	Remote Similarity	NPC488962
0.5467	Remote Similarity	NPC488964
0.5467	Remote Similarity	NPC184512
0.5455	Remote Similarity	NPC609097
0.5417	Remote Similarity	NPC488656
0.5405	Remote Similarity	NPC609715
0.5333	Remote Similarity	NPC488963
0.5309	Remote Similarity	NPC230331
0.527	Remote Similarity	NPC609880
0.5263	Remote Similarity	NPC252296
0.5205	Remote Similarity	NPC488653
0.5205	Remote Similarity	NPC479937
0.5195	Remote Similarity	NPC119550
0.5139	Remote Similarity	NPC132395
0.5139	Remote Similarity	NPC471364
0.5122	Remote Similarity	NPC267469
0.5122	Remote Similarity	NPC470024

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473204 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7301
0.1-0.2	1843
0.2-0.3	6
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