NPASS Compound

Natural Product: NPC472993

Natural Product ID	NPC472993
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RFBRMMMSAPRGDM-TUYFOBMESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3597471
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 72 76 0 0 0 0 0 0 0 0999 V2000 11.0087 -1.3457 -0.4106 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4267 -0.7668 -1.5593 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0461 -0.7155 -1.6696 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5195 -0.1457 -2.7985 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1577 -0.0954 -2.9068 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3479 -0.6102 -1.8954 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8297 -1.1854 -0.7551 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2444 -1.2201 -0.6778 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0657 -1.7194 0.3271 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8240 -1.7920 0.5847 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5627 -1.4392 0.0430 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5112 -1.7751 0.7709 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1794 -0.8098 -1.0978 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9100 -0.4986 -1.5551 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1455 0.4067 -0.6521 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8588 1.7525 -0.4612 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1470 2.4199 0.6985 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3343 2.4544 0.5215 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9128 1.1811 -0.0683 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1217 0.7129 -1.1248 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1161 0.2308 0.9160 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2994 -0.3193 1.3000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3423 -1.2813 2.3287 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5408 -1.8235 2.7015 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7494 -1.4829 2.1215 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7225 -0.5459 1.1169 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4937 0.0109 0.7338 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8359 -0.2092 0.5580 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0191 -0.6777 0.8541 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0992 -1.6177 1.8525 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9425 -2.0414 2.5127 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9741 -2.8921 3.4236 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2273 -0.2455 0.1756 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4888 -0.7006 0.4442 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6100 -0.2543 -0.2336 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4788 0.6903 -1.2281 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2259 1.1675 -1.5220 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1097 0.7078 -0.8307 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6069 1.1288 -1.8987 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5522 -2.7666 3.7153 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9013 2.5692 1.8120 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6060 3.6970 0.9313 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1884 1.5652 -0.1529 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3512 0.3687 -3.8091 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1027 -1.2001 -0.3738 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5538 -0.9140 0.5202 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7567 -2.4239 -0.4167 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7191 0.3463 -3.7821 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3037 -0.5425 -2.0532 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6608 -1.6650 0.2045 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7272 -2.1995 1.1601 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6545 -2.3346 1.6239 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2714 -1.3833 -1.7611 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0312 0.0017 -2.5598 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0530 -0.0213 0.3602 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7062 2.3939 -1.3527 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3579 1.7820 1.5998 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6914 3.3495 -0.0277 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8612 1.4839 -0.5441 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3925 -1.5403 2.7751 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5865 0.7335 -0.0613 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0196 -2.0837 2.1923 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6276 -1.4365 1.2127 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6040 -0.6172 -0.0175 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1417 1.9087 -2.3055 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1369 1.0820 -1.0629 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5119 1.9371 -2.4978 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1599 -3.6905 3.5871 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5940 1.8277 2.3923 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0916 3.7370 1.7989 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5714 2.4566 0.0448 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5402 1.3819 -3.7916 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 2 3 10 11 1 0 11 12 2 0 11 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 1 0 19 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 29 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 36 39 1 0 24 40 1 0 18 41 1 0 17 42 1 0 16 43 1 0 4 44 1 0 8 3 1 0 20 15 1 0 27 22 1 0 31 25 1 0 38 33 1 0 1 45 1 0 1 46 1 0 1 47 1 0 5 48 1 0 6 49 1 0 8 50 1 0 9 51 1 0 10 52 1 0 14 53 1 0 14 54 1 0 15 55 1 0 16 56 1 0 17 57 1 0 18 58 1 0 19 59 1 0 23 60 1 0 27 61 1 0 30 62 1 0 34 63 1 0 35 64 1 0 37 65 1 0 38 66 1 0 39 67 1 0 40 68 1 0 41 69 1 0 42 70 1 0 43 71 1 0 44 72 1 0 M END

Standard InCHIKey	RFBRMMMSAPRGDM-TUYFOBMESA-N
Standard InCHI	InChI=1S/C31H28O13/c1-40-23-10-15(2-8-19(23)33)3-9-26(36)41-14-25-28(37)29(38)30(39)31(44-25)42-18-11-20(34)27-21(35)13-22(43-24(27)12-18)16-4-6-17(32)7-5-16/h2-13,25,28-34,37-39H,14H2,1H3/b9-3+/t25-,28-,29+,30-,31-/m1/s1
SMILES	COC1=C(C=CC(=C1)C=CC(=O)OCC2C(C(C(C(O2)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	608.15	Volume:	581.949 ? Van der Waals volume.
Dense:	1.045	LogP:	1.57 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.731 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.316 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	32.0
TPSA:	205.58 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.125	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.146	Fsp³:	0.226
MCE-18:	104.421 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.749	Fluc inhibitor:	0.757 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.989 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.997 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.053	Promiscuous compounds:	0.866

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.124	MDCK Permeability:	-5.291
Pgp-inhibitor:	0.001	Pgp-substrate:	0.156
PAMPA:	0.984 ? 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):	0.748
20% Bioavailability (F20%):	0.989	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.663
Plasma Protein Binding (PPB):	85.74%	Volume Distribution (VD):	-0.146
Fu:	12.834% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.984
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.586
BSEP inhibitor:	0.681

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.007	CYP2D6-substrate:	0.966
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.962
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.03 ? 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):

2.696

Half-life (T1/2):

2.591

ADMET: Toxicity

hERG Blockers:	0.128	hERG Blockers (10um):	0.638
Human Hepatotoxicity (H-HT):	0.391	Drug-induced Liver Injury (DILI):	0.898
AMES Toxicity:	0.821	Rat Oral Acute Toxicity:	0.335
Maximum Recommended Daily Dose:	0.884	Skin Sensitization:	0.819
Carcinogencity:	0.393	Eye Corrosion:	0.0
Eye Irritation:	0.127	Respiratory Toxicity:	0.167
Drug-induced Neurotoxicity:	0.057	Ototoxicity:	0.702
Hematotoxicity:	0.01	Drug-induced Nephrotoxicity:	0.1
Genotoxicity:	0.853	RPMI-8226 Immunitoxicity:	0.144
A549 Cytotoxicity:	0.563	Hek293 Cytotoxicity:	0.968
BCF:	0.72 ? 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:	3.509 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.835 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.213 ? 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
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20356064]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22283497]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	leaf	Putz City, Chiayi County, Taiwan	2009-Nov	PMID[25999202]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28742368]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29397715]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26700	Tinospora crispa	Species	Menispermaceae	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	1

Activity Type	# Activity
Others	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
NPT2	Others	Unspecified	n.a.	IC50	=	8800.0	nM	PMID[21920741]

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 NPC472993 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	18506
0.1-0.2	26181
0.2-0.3	3820
0.3-0.4	944
0.4-0.5	284
0.5-0.6	78
0.6-0.7	33
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8989	High Similarity	NPC270675
0.8989	High Similarity	NPC195685
0.8495	Intermediate Similarity	NPC472994
0.8333	Intermediate Similarity	NPC480796
0.7526	Intermediate Similarity	NPC80068
0.7172	Intermediate Similarity	NPC477629
0.6939	Remote Similarity	NPC64051
0.6923	Remote Similarity	NPC473278
0.6827	Remote Similarity	NPC470416
0.6789	Remote Similarity	NPC471030
0.6667	Remote Similarity	NPC27942
0.6637	Remote Similarity	NPC199172
0.6633	Remote Similarity	NPC44931
0.6436	Remote Similarity	NPC46202
0.6327	Remote Similarity	NPC172807
0.6311	Remote Similarity	NPC229409
0.6286	Remote Similarity	NPC101636
0.6286	Remote Similarity	NPC298171
0.6286	Remote Similarity	NPC36138
0.6239	Remote Similarity	NPC217520
0.6238	Remote Similarity	NPC22062
0.6238	Remote Similarity	NPC473634
0.6238	Remote Similarity	NPC138811
0.6237	Remote Similarity	NPC331652
0.6195	Remote Similarity	NPC470717
0.619	Remote Similarity	NPC85751
0.619	Remote Similarity	NPC19240
0.617	Remote Similarity	NPC39360
0.617	Remote Similarity	NPC29763
0.617	Remote Similarity	NPC210003
0.6154	Remote Similarity	NPC210961
0.6154	Remote Similarity	NPC209296
0.614	Remote Similarity	NPC470720
0.614	Remote Similarity	NPC488079
0.614	Remote Similarity	NPC488078
0.6111	Remote Similarity	NPC599948
0.6042	Remote Similarity	NPC181712
0.6017	Remote Similarity	NPC35924
0.6	Remote Similarity	NPC473623
0.596	Remote Similarity	NPC311830
0.5943	Remote Similarity	NPC488089
0.5926	Remote Similarity	NPC223426
0.5922	Remote Similarity	NPC210073
0.59	Remote Similarity	NPC190003
0.5872	Remote Similarity	NPC214621
0.5872	Remote Similarity	NPC34267
0.5856	Remote Similarity	NPC477895
0.5841	Remote Similarity	NPC139571
0.5833	Remote Similarity	NPC260504
0.5833	Remote Similarity	NPC89809
0.5816	Remote Similarity	NPC471405
0.578	Remote Similarity	NPC484301
0.5773	Remote Similarity	NPC95090
0.5773	Remote Similarity	NPC27408
0.5755	Remote Similarity	NPC65711
0.5739	Remote Similarity	NPC295625
0.5727	Remote Similarity	NPC603856
0.57	Remote Similarity	NPC22832
0.57	Remote Similarity	NPC601144
0.5686	Remote Similarity	NPC211594
0.5667	Remote Similarity	NPC25946
0.5641	Remote Similarity	NPC470719
0.5636	Remote Similarity	NPC179862
0.5631	Remote Similarity	NPC254540
0.5603	Remote Similarity	NPC474093
0.5603	Remote Similarity	NPC104910
0.5586	Remote Similarity	NPC81042
0.5579	Remote Similarity	NPC291153
0.5556	Remote Similarity	NPC10205
0.5545	Remote Similarity	NPC243930
0.5545	Remote Similarity	NPC476869
0.5536	Remote Similarity	NPC121703
0.5526	Remote Similarity	NPC164704
0.551	Remote Similarity	NPC19709
0.5472	Remote Similarity	NPC473512
0.5472	Remote Similarity	NPC129827
0.5455	Remote Similarity	NPC189142
0.5455	Remote Similarity	NPC77660
0.5398	Remote Similarity	NPC11468
0.5366	Remote Similarity	NPC21359
0.5366	Remote Similarity	NPC460984
0.5364	Remote Similarity	NPC479644
0.534	Remote Similarity	NPC607707
0.5294	Remote Similarity	NPC282169
0.5294	Remote Similarity	NPC298666
0.5278	Remote Similarity	NPC186816
0.5273	Remote Similarity	NPC139060
0.5273	Remote Similarity	NPC476620
0.5259	Remote Similarity	NPC470715
0.5248	Remote Similarity	NPC291296
0.5238	Remote Similarity	NPC476865
0.5227	Remote Similarity	NPC234133
0.52	Remote Similarity	NPC261866
0.5189	Remote Similarity	NPC479767
0.5169	Remote Similarity	NPC488087
0.5169	Remote Similarity	NPC470716
0.5149	Remote Similarity	NPC93337
0.5138	Remote Similarity	NPC204693
0.51	Remote Similarity	NPC473043
0.5098	Remote Similarity	NPC46420
0.5098	Remote Similarity	NPC105025
0.5094	Remote Similarity	NPC4390
0.5094	Remote Similarity	NPC477848
0.5093	Remote Similarity	NPC11411
0.5093	Remote Similarity	NPC300262
0.5089	Remote Similarity	NPC479766
0.5089	Remote Similarity	NPC486577
0.5088	Remote Similarity	NPC470450
0.5083	Remote Similarity	NPC488086
0.5051	Remote Similarity	NPC157898
0.505	Remote Similarity	NPC108831
0.505	Remote Similarity	NPC182634
0.5049	Remote Similarity	NPC198324
0.5048	Remote Similarity	NPC476868
0.5046	Remote Similarity	NPC65003
0.5044	Remote Similarity	NPC479765
0.5044	Remote Similarity	NPC188815

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472993 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4257
0.1-0.2	4795
0.2-0.3	85
0.3-0.4	8
0.4-0.5	4
0.5-0.6	0
0.6-0.7	1
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
0.6154	Remote Similarity	NPD7054	Phase 4

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