NPASS Compound

Natural Product: NPC472994

Natural Product ID	NPC472994
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XOLPIGVCJFIOOY-PWTWCKKXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3597475
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 67 71 0 0 0 0 0 0 0 0999 V2000 9.2568 2.9340 2.7294 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7650 3.0815 1.4558 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0190 2.6705 0.3801 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7316 2.0922 0.4944 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2842 1.9744 1.7655 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0247 2.3850 2.8995 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0432 1.7674 -0.6980 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0236 1.0653 -0.9766 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0989 0.2728 -0.2423 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0363 0.0110 0.9762 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0161 -0.3761 -0.9465 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0989 -1.1538 -0.2102 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0589 -1.6560 -1.1808 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6547 -2.3845 -2.3605 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5882 -2.8195 -3.3049 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2535 -2.3440 -2.8789 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0454 -2.5392 -1.4292 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0799 -2.4511 -0.5907 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9121 -1.5343 -0.9801 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2334 -1.6442 -0.7350 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9207 -2.8002 -0.9737 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2828 -2.8705 -0.7062 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9278 -1.7619 -0.1988 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2783 -0.5754 0.0582 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9353 -0.5366 -0.2158 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9170 0.4624 0.5401 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1957 0.4854 0.8201 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9189 -0.6623 0.5911 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2797 -1.7959 0.0771 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9087 -2.8589 -0.1440 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8184 1.7147 1.3627 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1513 1.8022 1.6734 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6468 3.0060 2.1840 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8307 4.1029 2.3823 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5018 4.0101 2.0705 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0298 2.8252 1.5707 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3408 5.3075 2.8972 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0066 -4.0302 -0.9380 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0236 -1.0531 -3.3446 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8639 -2.2157 -4.5582 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3875 -3.4654 -1.8512 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8743 3.2709 3.5577 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7412 3.5128 1.2584 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4352 2.7886 -0.6216 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3105 1.5930 1.9840 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6255 2.2680 3.8857 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5074 2.2802 -1.6553 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7828 1.0656 -2.1263 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6536 -0.5532 0.6051 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6437 -1.9871 0.2732 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4830 -0.7810 -1.6183 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3336 -1.6809 -2.8647 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5786 -3.9192 -3.4753 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4965 -2.9891 -3.4429 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5472 -3.5182 -1.3086 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4835 -3.7121 -1.3740 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3696 0.3505 -0.0404 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9727 -0.7049 0.8020 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8057 0.9803 1.5341 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6908 3.1044 2.4395 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8199 4.8348 2.2025 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9815 2.7562 1.3234 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3371 5.4196 3.0535 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6350 -4.9656 -0.8301 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1981 -1.0297 -4.3082 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4767 -2.7279 -5.3029 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7122 -4.0977 -1.4909 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 5 6 2 0 4 7 1 0 7 8 2 3 8 9 1 0 9 10 2 0 9 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 17 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 27 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 34 37 1 0 22 38 1 0 16 39 1 0 15 40 1 0 14 41 1 0 6 1 1 0 18 13 1 0 25 20 1 0 29 23 1 0 36 31 1 0 1 42 1 0 2 43 1 0 3 44 1 0 5 45 1 0 6 46 1 0 7 47 1 0 8 48 1 0 12 49 1 0 12 50 1 0 13 51 1 0 14 52 1 0 15 53 1 0 16 54 1 0 17 55 1 0 21 56 1 0 25 57 1 0 28 58 1 0 32 59 1 0 33 60 1 0 35 61 1 0 36 62 1 0 37 63 1 0 38 64 1 0 39 65 1 0 40 66 1 0 41 67 1 0 M END

Standard InCHIKey	XOLPIGVCJFIOOY-PWTWCKKXSA-N
Standard InCHI	InChI=1S/C30H26O11/c31-18-9-7-17(8-10-18)22-14-21(33)26-20(32)12-19(13-23(26)40-22)39-30-29(37)28(36)27(35)24(41-30)15-38-25(34)11-6-16-4-2-1-3-5-16/h1-14,24,27-32,35-37H,15H2/b11-6-/t24-,27-,28+,29-,30-/m1/s1
SMILES	C1=CC=C(C=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

Calculated Properties

Physi-Chem Properties

Molecular Weight:	562.15	Volume:	547.072 ? Van der Waals volume.
Dense:	1.028	LogP:	2.183 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.375 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.99 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	32.0
TPSA:	176.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	5.0	Rings:	5.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.165	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.994	Fsp³:	0.2
MCE-18:	98.333 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.955	Fluc inhibitor:	0.903 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.987 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.993 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.143	Promiscuous compounds:	0.681

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.03	MDCK Permeability:	-5.15
Pgp-inhibitor:	0.023	Pgp-substrate:	0.099
PAMPA:	0.987 ? 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):	0.29
20% Bioavailability (F20%):	0.892	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007	MRP1:	0.533
Plasma Protein Binding (PPB):	92.325%	Volume Distribution (VD):	-0.221
Fu:	7.14% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.891
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.118
BSEP inhibitor:	0.888

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.003	CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.943
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.001 ? 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):

2.362

Half-life (T1/2):

2.035

ADMET: Toxicity

hERG Blockers:	0.162	hERG Blockers (10um):	0.665
Human Hepatotoxicity (H-HT):	0.43	Drug-induced Liver Injury (DILI):	0.924
AMES Toxicity:	0.802	Rat Oral Acute Toxicity:	0.334
Maximum Recommended Daily Dose:	0.894	Skin Sensitization:	0.875
Carcinogencity:	0.333	Eye Corrosion:	0.0
Eye Irritation:	0.17	Respiratory Toxicity:	0.124
Drug-induced Neurotoxicity:	0.14	Ototoxicity:	0.66
Hematotoxicity:	0.01	Drug-induced Nephrotoxicity:	0.09
Genotoxicity:	0.811	RPMI-8226 Immunitoxicity:	0.086
A549 Cytotoxicity:	0.467	Hek293 Cytotoxicity:	0.957
BCF:	1.025 ? 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:	3.899 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.045 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.647 ? 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	=	11300.0	nM	PMID[18271551]

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 NPC472994 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	15624
0.1-0.2	29215
0.2-0.3	3826
0.3-0.4	811
0.4-0.5	266
0.5-0.6	76
0.6-0.7	24
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC270675
0.9412	High Similarity	NPC195685
0.8495	Intermediate Similarity	NPC472993
0.7917	Intermediate Similarity	NPC473278
0.7849	Intermediate Similarity	NPC80068
0.7474	Intermediate Similarity	NPC477629
0.7234	Intermediate Similarity	NPC64051
0.7048	Intermediate Similarity	NPC471030
0.703	Intermediate Similarity	NPC480796
0.6915	Remote Similarity	NPC44931
0.6778	Remote Similarity	NPC27942
0.6566	Remote Similarity	NPC229409
0.6535	Remote Similarity	NPC101636
0.6535	Remote Similarity	NPC298171
0.6517	Remote Similarity	NPC331652
0.6444	Remote Similarity	NPC39360
0.6444	Remote Similarity	NPC29763
0.6444	Remote Similarity	NPC210003
0.6436	Remote Similarity	NPC85751
0.6436	Remote Similarity	NPC19240
0.64	Remote Similarity	NPC210961
0.6364	Remote Similarity	NPC46202
0.625	Remote Similarity	NPC172807
0.6214	Remote Similarity	NPC36138
0.6162	Remote Similarity	NPC22062
0.6162	Remote Similarity	NPC473634
0.6162	Remote Similarity	NPC210073
0.6162	Remote Similarity	NPC138811
0.6154	Remote Similarity	NPC223426
0.6146	Remote Similarity	NPC190003
0.6058	Remote Similarity	NPC260504
0.6058	Remote Similarity	NPC89809
0.6038	Remote Similarity	NPC599948
0.598	Remote Similarity	NPC65711
0.5957	Remote Similarity	NPC181712
0.5943	Remote Similarity	NPC214621
0.5943	Remote Similarity	NPC34267
0.5922	Remote Similarity	NPC473623
0.5922	Remote Similarity	NPC209296
0.5872	Remote Similarity	NPC217520
0.5865	Remote Similarity	NPC488089
0.5849	Remote Similarity	NPC179862
0.5849	Remote Similarity	NPC484301
0.5824	Remote Similarity	NPC291153
0.578	Remote Similarity	NPC477895
0.5745	Remote Similarity	NPC19709
0.5727	Remote Similarity	NPC164704
0.5688	Remote Similarity	NPC470416
0.5684	Remote Similarity	NPC95090
0.5684	Remote Similarity	NPC27408
0.5684	Remote Similarity	NPC189142
0.5684	Remote Similarity	NPC77660
0.5648	Remote Similarity	NPC81042
0.5648	Remote Similarity	NPC603856
0.5612	Remote Similarity	NPC601144
0.56	Remote Similarity	NPC211594
0.5593	Remote Similarity	NPC199172
0.5556	Remote Similarity	NPC311830
0.5545	Remote Similarity	NPC254540
0.551	Remote Similarity	NPC282169
0.5481	Remote Similarity	NPC186816
0.5478	Remote Similarity	NPC298666
0.5472	Remote Similarity	NPC139060
0.5472	Remote Similarity	NPC476620
0.5455	Remote Similarity	NPC22832
0.5455	Remote Similarity	NPC243930
0.5455	Remote Similarity	NPC121703
0.5446	Remote Similarity	NPC470715
0.5417	Remote Similarity	NPC261866
0.5385	Remote Similarity	NPC473512
0.5385	Remote Similarity	NPC129827
0.5351	Remote Similarity	NPC139571
0.5351	Remote Similarity	NPC470716
0.5315	Remote Similarity	NPC11468
0.5312	Remote Similarity	NPC473043
0.5306	Remote Similarity	NPC10205
0.5258	Remote Similarity	NPC108831
0.5258	Remote Similarity	NPC182634
0.5248	Remote Similarity	NPC607707
0.5238	Remote Similarity	NPC65003
0.5229	Remote Similarity	NPC188815
0.5204	Remote Similarity	NPC323593
0.5204	Remote Similarity	NPC203500
0.5169	Remote Similarity	NPC470717
0.5155	Remote Similarity	NPC137813
0.5146	Remote Similarity	NPC477848
0.5143	Remote Similarity	NPC67105
0.514	Remote Similarity	NPC470125
0.5138	Remote Similarity	NPC294722
0.5135	Remote Similarity	NPC218161
0.5126	Remote Similarity	NPC470720
0.5126	Remote Similarity	NPC488079
0.5126	Remote Similarity	NPC488078
0.5116	Remote Similarity	NPC234133
0.5104	Remote Similarity	NPC157898
0.5102	Remote Similarity	NPC249281
0.51	Remote Similarity	NPC198324
0.5093	Remote Similarity	NPC477628
0.5089	Remote Similarity	NPC96605
0.5089	Remote Similarity	NPC280642
0.5086	Remote Similarity	NPC488087
0.5051	Remote Similarity	NPC93337
0.5051	Remote Similarity	NPC297987
0.5051	Remote Similarity	NPC146792
0.505	Remote Similarity	NPC204937
0.5049	Remote Similarity	NPC276377
0.5047	Remote Similarity	NPC122809
0.5047	Remote Similarity	NPC204693
0.5041	Remote Similarity	NPC35924

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472994 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3399
0.1-0.2	5623
0.2-0.3	114
0.3-0.4	8
0.4-0.5	5
0.5-0.6	1
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
0.5922	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