NPASS Compound

Natural Product: NPC297512

Natural Product ID	NPC297512
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CHTVZEGPHZDBTO-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003504] 8-prenylated flavones

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 61 63 0 0 0 0 0 0 0 0999 V2000 6.0201 -2.0209 0.9861 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3603 -1.4976 -0.2338 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1093 -1.0779 -0.2983 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1928 -1.0749 0.8573 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6195 0.2653 1.1509 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3739 1.2356 1.7699 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7882 2.4742 2.0180 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 2.7165 1.6542 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7312 1.7413 1.0303 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5700 2.0039 0.6780 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0900 3.1158 0.9053 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2669 0.9487 0.0524 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6928 1.2235 -0.2100 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3931 1.4344 1.1311 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0749 2.5126 1.4239 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2591 3.6492 0.5180 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7105 2.5843 2.7824 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6953 -0.2481 -0.1962 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3677 -1.3448 -0.8404 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2519 -2.6099 -0.2546 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7571 -3.7510 -0.8307 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4155 -3.6587 -2.0511 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5313 -2.4256 -2.6309 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0098 -1.2650 -2.0346 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1627 -0.0894 -2.6951 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8293 -0.0137 -3.9335 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9263 -4.7952 -2.6348 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6089 -4.9810 -0.1966 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5817 -0.4060 0.1914 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2919 0.5125 0.7767 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8613 3.9428 1.8814 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6912 1.0465 2.1618 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1638 -1.4367 -1.4957 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1171 -1.8123 0.8981 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8540 -3.1324 1.0690 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6389 -1.4771 1.8528 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6894 -0.7011 -1.2512 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3359 -1.7521 0.5691 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6269 -1.5368 1.7542 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3394 3.2807 2.5054 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9240 1.9938 -0.9009 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1551 0.2476 -0.5613 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2714 0.6061 1.8176 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2639 3.5293 0.0203 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3543 4.6065 1.0870 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4654 3.8193 -0.2183 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5719 1.8650 2.7495 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1082 3.5878 2.9873 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9804 2.3245 3.5560 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7424 -2.7309 0.7049 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0450 -2.3598 -3.5827 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2899 -0.6107 -4.7230 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9798 1.0475 -4.2608 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8238 -0.4856 -3.8090 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8721 -5.1173 -2.4028 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3418 -5.3785 0.3915 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4908 4.0602 2.8263 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3933 1.7711 2.1522 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1822 -0.4036 -1.8818 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1768 -1.8109 -1.3353 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6779 -2.1405 -2.2222 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 2 3 15 16 1 0 15 17 1 0 12 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 22 27 1 0 21 28 1 0 18 29 1 0 29 30 1 0 8 31 1 0 6 32 1 0 2 33 1 0 30 5 1 0 30 9 2 0 24 19 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 4 38 1 0 4 39 1 0 7 40 1 0 13 41 1 0 13 42 1 0 14 43 1 0 16 44 1 0 16 45 1 0 16 46 1 0 17 47 1 0 17 48 1 0 17 49 1 0 20 50 1 0 23 51 1 0 26 52 1 0 26 53 1 0 26 54 1 0 27 55 1 0 28 56 1 0 31 57 1 0 32 58 1 0 33 59 1 0 33 60 1 0 33 61 1 0 M END

Standard InCHIKey	CHTVZEGPHZDBTO-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C26H28O7/c1-13(2)6-8-15-18(27)11-21(30)23-24(31)16(9-7-14(3)4)25(33-26(15)23)17-10-19(28)20(29)12-22(17)32-5/h6-7,10-12,27-30H,8-9H2,1-5H3
SMILES	CC(=CCc1c(cc(c2c(=O)c(CC=C(C)C)c(c3cc(c(cc3OC)O)O)oc12)O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	452.18	Volume:	467.75 ? Van der Waals volume.
Dense:	0.967	LogP:	4.778 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.746 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.115 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	20.0
TPSA:	120.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.295	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.207	Fsp³:	0.269
MCE-18:	23.0 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.944	Fluc inhibitor:	0.293 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.997 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.772 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.313	Promiscuous compounds:	0.196

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.025	MDCK Permeability:	-4.735
Pgp-inhibitor:	0.169	Pgp-substrate:	0.074
PAMPA:	0.363 ? 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):	0.152
20% Bioavailability (F20%):	0.992	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.966
Plasma Protein Binding (PPB):	93.82%	Volume Distribution (VD):	0.208
Fu:	5.902% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.98	BCRP inhibitor:	0.988
BSEP inhibitor:	0.622

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.905	CYP2D6-substrate:	0.979
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

6.418

Half-life (T1/2):

1.698

ADMET: Toxicity

hERG Blockers:	0.019	hERG Blockers (10um):	0.585
Human Hepatotoxicity (H-HT):	0.472	Drug-induced Liver Injury (DILI):	0.717
AMES Toxicity:	0.629	Rat Oral Acute Toxicity:	0.852
Maximum Recommended Daily Dose:	0.571	Skin Sensitization:	0.989
Carcinogencity:	0.229	Eye Corrosion:	0.0
Eye Irritation:	0.34	Respiratory Toxicity:	0.98
Drug-induced Neurotoxicity:	0.059	Ototoxicity:	0.417
Hematotoxicity:	0.074	Drug-induced Nephrotoxicity:	0.208
Genotoxicity:	0.993	RPMI-8226 Immunitoxicity:	0.021
A549 Cytotoxicity:	0.638	Hek293 Cytotoxicity:	0.581
BCF:	1.925 ? 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:	5.192 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.872 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.335 ? 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
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21954959]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	roots	Whitessence Srl, Viterbo, Italy	2005-OCT	PMID[21954959]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	DingXi, GanSu, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	LanZhou, GanSu, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	80 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	70 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	60 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	50 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	90 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	40 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	Maturation	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	30 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	20 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	10 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	Maturation	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	90 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	80 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	70 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	60 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	50 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	40 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	30 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	20 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	10 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14309	Desmodium tortuosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7819.1	Epichloe festucae var. lolii	Varieties	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15554	Eucalyptus amplifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14430	Grateloupia carnosa	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14058	Papaver pavoninum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12131	Salvia calycina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14058	Papaver pavoninum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7819.1	Epichloe festucae var. lolii	Varieties	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14430	Grateloupia carnosa	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14309	Desmodium tortuosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15554	Eucalyptus amplifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12131	Salvia calycina	Species	Lamiaceae	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

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

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 NPC297512 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	22939
0.1-0.2	23062
0.2-0.3	3422
0.3-0.4	352
0.4-0.5	69
0.5-0.6	10
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	Natural Product ID
0.6324	Remote Similarity	NPC96565
0.5733	Remote Similarity	NPC479191
0.5714	Remote Similarity	NPC77856
0.5584	Remote Similarity	NPC469658
0.5507	Remote Similarity	NPC63187
0.5429	Remote Similarity	NPC88804
0.5417	Remote Similarity	NPC273538
0.5405	Remote Similarity	NPC249570
0.5263	Remote Similarity	NPC471982
0.5135	Remote Similarity	NPC36852
0.5122	Remote Similarity	NPC276444

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC297512 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3967
0.1-0.2	5139
0.2-0.3	42
0.3-0.4	1
0.4-0.5	0
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
0.5417	Remote Similarity	NPD4378	Phase 3

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