NPASS Compound

Natural Product: NPC473207

Natural Product ID	NPC473207
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(5S,6As,7R,8R,10S,10As)-1,3-Diacetyloxy-10-Hydroxy-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	[(5S,6aS,7R,8R,10S,10aS)-1,3-diacetyloxy-10-hydroxy-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	CHEMBL366249
PubChem CID	44404746
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 79 81 0 0 0 0 0 0 0 0999 V2000 -4.2378 4.4227 2.8804 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5795 3.3246 2.6605 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8055 2.5751 1.4176 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1583 1.4561 1.1653 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2591 0.5974 0.0015 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9270 0.4725 -0.7736 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5984 1.9284 -1.1779 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2352 -0.2612 -2.0239 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6458 -0.8736 -2.0623 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2162 -1.1909 -2.5651 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0150 -1.4103 -1.7711 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2887 -1.3964 -0.2991 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8836 -0.0944 0.1381 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1268 0.9819 0.4210 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4524 0.5407 0.8942 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5314 1.1092 0.1251 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4928 1.9312 0.6401 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4143 2.2020 1.8851 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5814 2.4907 -0.1903 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4195 1.3904 -0.8084 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5104 2.0256 -1.6419 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0504 3.4492 -1.2325 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7159 -0.8869 0.9596 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9447 -1.7717 0.4297 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9633 -3.2932 0.3565 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2000 -3.6387 -0.2746 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1072 -2.6163 0.0787 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2920 -2.5625 1.4731 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4798 -2.7420 2.1308 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5035 -2.9757 1.4676 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4671 -2.6439 3.6183 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0707 -3.7867 -0.3147 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9155 -4.6823 0.3219 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6391 -5.0155 1.4995 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1201 -5.2528 -0.3341 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5055 -2.6763 -2.0892 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7675 3.0976 0.4350 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9457 4.7949 2.1713 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0789 4.9792 3.7882 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8681 2.9684 3.3954 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4572 1.1516 1.9533 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1049 0.8263 -0.6160 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4742 -0.4489 0.4109 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4167 2.5764 -0.3240 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5730 2.3225 -1.6136 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9105 1.9838 -2.0219 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3393 0.5294 -2.8473 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5823 -1.5785 -2.9517 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8561 -1.5309 -1.2166 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4220 -0.1604 -2.3440 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8821 -0.9654 -3.6216 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7251 -2.1949 -2.6868 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 -0.6951 -2.0034 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3738 -0.3201 1.1096 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2732 1.7236 1.1450 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3350 1.6050 -0.5019 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6497 0.9555 1.9358 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2581 3.0734 0.4628 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7693 0.7625 -1.4350 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9063 0.8457 0.0201 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3662 3.1178 -1.7631 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5329 1.5502 -2.6333 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5179 1.9060 -1.1615 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9685 3.5989 -1.0369 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5134 4.4634 -1.1503 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2396 2.9965 -2.2304 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6148 -1.2256 1.4862 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9177 -3.7220 1.3781 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9861 -2.8062 -0.5116 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3762 -3.0813 4.0668 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4296 -1.5845 3.9545 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5348 -3.1236 3.9823 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2675 -4.8179 -1.3333 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9028 -6.3392 -0.4857 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0204 -5.2097 0.3035 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3248 -2.9491 -3.0075 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8303 2.9369 0.7601 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6929 2.6580 -0.5686 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6269 4.2034 0.3007 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 6 5 1 1 6 7 1 0 6 8 1 0 8 9 1 0 8 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 2 0 17 19 1 0 19 20 1 0 20 21 1 0 19 22 1 0 15 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 25 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 11 36 1 0 3 37 1 0 13 6 1 0 12 27 1 6 24 12 1 0 1 38 1 0 1 39 1 0 2 40 1 0 4 41 1 0 5 42 1 0 5 43 1 0 7 44 1 0 7 45 1 0 7 46 1 0 8 47 1 6 9 48 1 0 9 49 1 0 9 50 1 0 10 51 1 0 10 52 1 0 11 53 1 1 13 54 1 1 14 55 1 0 14 56 1 0 15 57 1 1 19 58 1 0 20 59 1 0 20 60 1 0 21 61 1 0 21 62 1 0 21 63 1 0 22 64 1 0 22 65 1 0 22 66 1 0 23 67 1 0 25 68 1 0 27 69 1 0 31 70 1 0 31 71 1 0 31 72 1 0 35 73 1 0 35 74 1 0 35 75 1 0 36 76 1 0 37 77 1 0 37 78 1 0 37 79 1 0 M END

Standard InCHIKey	FGGPIWICAGRSLN-FBIWMMQLSA-N
Standard InCHI	InChI=1S/C29H42O8/c1-9-16(3)11-12-28(8)18(5)13-24(32)29-22(26(34-19(6)30)37-27(29)35-20(7)31)14-21(15-23(28)29)36-25(33)17(4)10-2/h9,11,14,17-18,21,23-24,26-27,32H,1,10,12-13,15H2,2-8H3/b16-11+/t17?,18-,21-,23+,24+,26?,27?,28-,29-/m1/s1
SMILES	C=C/C(=C/C[C@]1(C)[C@H](C)C[C@@H]([C@@]23[C@H]1C[C@H](OC(=O)C(CC)C)C=C3C(OC2OC(=O)C)OC(=O)C)O)/C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	518.29	Volume:	538.974 ? Van der Waals volume.
Dense:	0.962	LogP:	3.607 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.417 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.406 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	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:	0.215	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.824	Fsp³:	0.69
MCE-18:	92.02 ? 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:	0.562	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.006 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.344	Promiscuous compounds:	0.137

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.088	MDCK Permeability:	-4.76
Pgp-inhibitor:	0.858	Pgp-substrate:	0.875
PAMPA:	0.172 ? 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):	0.006
20% Bioavailability (F20%):	0.988	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011	MRP1:	0.996
Plasma Protein Binding (PPB):	64.506%	Volume Distribution (VD):	-0.179
Fu:	32.678% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.976	BCRP inhibitor:	0.488
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.011	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.466	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.943 ? 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):

7.493

Half-life (T1/2):

0.837

ADMET: Toxicity

hERG Blockers:	0.098	hERG Blockers (10um):	0.444
Human Hepatotoxicity (H-HT):	0.595	Drug-induced Liver Injury (DILI):	0.837
AMES Toxicity:	0.864	Rat Oral Acute Toxicity:	0.908
Maximum Recommended Daily Dose:	0.987	Skin Sensitization:	0.94
Carcinogencity:	0.651	Eye Corrosion:	0.0
Eye Irritation:	0.007	Respiratory Toxicity:	0.578
Drug-induced Neurotoxicity:	0.878	Ototoxicity:	0.708
Hematotoxicity:	0.627	Drug-induced Nephrotoxicity:	0.897
Genotoxicity:	0.983	RPMI-8226 Immunitoxicity:	0.294
A549 Cytotoxicity:	0.509	Hek293 Cytotoxicity:	0.429
BCF:	0.782 ? 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:	3.786 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.699 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.087 ? 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	=	0.85	uM	PMID[21456549]
NPT83	Cell line	MCF7	Homo sapiens	Ratio	=	1.3	n.a.	PMID[21456549]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	0.57	uM	PMID[17958396]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	0.59	uM	PMID[17958396]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	Activity	=	10.5	uM	PMID[17958396]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	Activity	=	11.0	uM	PMID[19296669]

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 NPC473207 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	18459
0.1-0.2	27512
0.2-0.3	3738
0.3-0.4	45
0.4-0.5	31
0.5-0.6	27
0.6-0.7	10
0.7-0.8	0
0.8-0.85	5
0.85-0.9	7
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC330003
1.0	High Similarity	NPC470321
1.0	High Similarity	NPC264867
0.9333	High Similarity	NPC488658
0.9333	High Similarity	NPC488655
0.9167	High Similarity	NPC329623
0.8983	High Similarity	NPC602188
0.8548	High Similarity	NPC201880
0.8548	High Similarity	NPC488660
0.8548	High Similarity	NPC488657
0.8548	High Similarity	NPC81567
0.8548	High Similarity	NPC488652
0.8548	High Similarity	NPC609711
0.8361	Intermediate Similarity	NPC488659
0.8361	Intermediate Similarity	NPC604149
0.8154	Intermediate Similarity	NPC488964
0.8154	Intermediate Similarity	NPC184512
0.8125	Intermediate Similarity	NPC609715
0.7969	Intermediate Similarity	NPC134270
0.7969	Intermediate Similarity	NPC488654
0.7969	Intermediate Similarity	NPC609880
0.7937	Intermediate Similarity	NPC488656
0.7846	Intermediate Similarity	NPC475889
0.7846	Intermediate Similarity	NPC7613
0.7846	Intermediate Similarity	NPC479942
0.7612	Intermediate Similarity	NPC252296
0.7385	Intermediate Similarity	NPC488653
0.7313	Intermediate Similarity	NPC238397
0.7164	Intermediate Similarity	NPC479491
0.7162	Intermediate Similarity	NPC109376
0.7143	Intermediate Similarity	NPC127933
0.7123	Intermediate Similarity	NPC116292
0.7101	Intermediate Similarity	NPC471363
0.6866	Remote Similarity	NPC479943
0.6716	Remote Similarity	NPC488235
0.6667	Remote Similarity	NPC311223
0.6667	Remote Similarity	NPC479940
0.6667	Remote Similarity	NPC7644
0.6667	Remote Similarity	NPC316974
0.6667	Remote Similarity	NPC479497
0.6522	Remote Similarity	NPC473204
0.6479	Remote Similarity	NPC479941
0.6081	Remote Similarity	NPC119550
0.5882	Remote Similarity	NPC603601
0.5875	Remote Similarity	NPC486751
0.5857	Remote Similarity	NPC600724
0.5789	Remote Similarity	NPC40728
0.5714	Remote Similarity	NPC606965
0.5698	Remote Similarity	NPC320734
0.5679	Remote Similarity	NPC316708
0.5672	Remote Similarity	NPC604446
0.5663	Remote Similarity	NPC224660
0.5658	Remote Similarity	NPC125423
0.5625	Remote Similarity	NPC87630
0.5625	Remote Similarity	NPC473216
0.5556	Remote Similarity	NPC88507
0.5467	Remote Similarity	NPC217921
0.5467	Remote Similarity	NPC88013
0.5467	Remote Similarity	NPC135015
0.5333	Remote Similarity	NPC311166
0.5333	Remote Similarity	NPC128795
0.527	Remote Similarity	NPC488236
0.5244	Remote Similarity	NPC473399
0.5244	Remote Similarity	NPC179128
0.5181	Remote Similarity	NPC162569
0.5181	Remote Similarity	NPC35160
0.5139	Remote Similarity	NPC98112
0.5067	Remote Similarity	NPC479937
0.5065	Remote Similarity	NPC473545
0.5065	Remote Similarity	NPC218158

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473207 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7074
0.1-0.2	2047
0.2-0.3	29
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