NPASS Compound

Natural Product: NPC238376

Natural Product ID	NPC238376
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QPHXPNUXTNHJOF-XNFUJFQVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5748601
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 52 55 0 0 0 0 0 0 0 0999 V2000 -5.3178 -2.8743 0.5833 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7727 -1.5550 0.0697 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8876 -0.8461 -0.6286 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7204 0.6387 -0.4368 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2406 0.9510 -0.4513 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5272 0.2775 0.7103 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2295 -0.8590 1.1294 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2466 -0.0169 0.2900 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0397 0.4270 0.7605 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9895 1.3065 1.8150 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2739 1.7126 2.2371 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4321 1.2632 1.6363 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3910 0.3808 0.5777 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1424 -0.0229 0.1579 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4731 -0.0560 -0.0039 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7120 0.2811 0.3363 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8300 -0.2920 -0.4111 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5618 -1.1787 -1.4599 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5389 -1.7692 -2.2216 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8689 -1.5056 -1.9782 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1564 -0.6404 -0.9563 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1445 -0.0376 -0.1780 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4700 -0.3489 -0.6787 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8431 -2.1118 -2.7586 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8086 1.1536 1.3799 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6811 1.6588 2.0462 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7782 2.4528 2.9955 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0431 1.5835 1.8319 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3717 2.6107 3.3115 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0998 2.3257 -0.2813 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2749 0.9502 0.8206 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8032 -1.1023 -1.9964 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7506 -2.6981 1.6100 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1588 -3.2411 -0.0362 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5142 -3.6243 0.7252 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9612 -1.8251 -0.6554 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8597 -1.1894 -0.2180 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2354 1.2295 -1.1950 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8174 0.5890 -1.3925 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5150 0.9814 1.5552 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8568 1.6958 2.3285 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0847 -0.7202 -0.6774 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5221 -1.3879 -1.6540 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2999 -2.4595 -3.0363 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4329 0.6335 0.6111 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0126 0.1802 -1.3567 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3411 -1.5798 -3.4682 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2353 2.5371 2.0883 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5735 2.1989 4.2157 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2482 2.5543 0.6729 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9613 1.6390 0.7708 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9949 -0.2701 -2.5277 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 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 21 23 1 0 20 24 1 0 16 25 2 0 25 26 1 0 26 27 2 0 25 28 1 0 11 29 1 0 5 30 1 0 4 31 1 0 3 32 1 0 7 2 1 0 14 9 1 0 22 17 1 0 26 12 1 0 1 33 1 0 1 34 1 0 1 35 1 0 2 36 1 6 3 37 1 1 4 38 1 6 5 39 1 6 6 40 1 1 10 41 1 0 14 42 1 0 18 43 1 0 19 44 1 0 22 45 1 0 23 46 1 0 24 47 1 0 28 48 1 0 29 49 1 0 30 50 1 0 31 51 1 0 32 52 1 0 M END

Standard InCHIKey	QPHXPNUXTNHJOF-XNFUJFQVSA-N
Standard InCHI	InChI=1S/C21H20O11/c1-7-15(25)17(27)19(29)21(30-7)31-9-5-12(24)14-13(6-9)32-20(18(28)16(14)26)8-2-3-10(22)11(23)4-8/h2-7,15,17,19,21-25,27-29H,1H3/t7-,15-,17+,19+,21-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1cc(c2c(c1)oc(c1ccc(c(c1)O)O)c(c2=O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	448.1	Volume:	413.147 ? Van der Waals volume.
Dense:	1.085	LogP:	1.152 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.401 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.039 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	24.0
TPSA:	190.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.276	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.018	Fsp³:	0.286
MCE-18:	91.0 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.649	Fluc inhibitor:	0.323 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.954 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.871 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.239	Promiscuous compounds:	0.861

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.226	MDCK Permeability:	-4.965
Pgp-inhibitor:	0.0	Pgp-substrate:	0.084
PAMPA:	0.99 ? 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):	0.928
20% Bioavailability (F20%):	0.673	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.452
Plasma Protein Binding (PPB):	84.436%	Volume Distribution (VD):	-0.225
Fu:	13.028% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.921
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.043	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.023
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.042
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.927
HLM stability:	0.483 ? 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):

3.376

Half-life (T1/2):

4.577

ADMET: Toxicity

hERG Blockers:	0.03	hERG Blockers (10um):	0.347
Human Hepatotoxicity (H-HT):	0.413	Drug-induced Liver Injury (DILI):	0.982
AMES Toxicity:	0.798	Rat Oral Acute Toxicity:	0.15
Maximum Recommended Daily Dose:	0.185	Skin Sensitization:	0.983
Carcinogencity:	0.099	Eye Corrosion:	0.001
Eye Irritation:	0.926	Respiratory Toxicity:	0.163
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.743
Hematotoxicity:	0.078	Drug-induced Nephrotoxicity:	0.15
Genotoxicity:	0.891	RPMI-8226 Immunitoxicity:	0.081
A549 Cytotoxicity:	0.867	Hek293 Cytotoxicity:	0.342
BCF:	0.724 ? 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:	3.452 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.733 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.185 ? 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
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 3619437]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/btpr.97]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11738-010-0631-6]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.plaphy.2018.10.015]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1080/17429145.2017.1293852]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1186/1750-2187-3-9]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11914965]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12628396]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	Leaves and branches	Soorkesh Valley, Gollestan, Iran	n.a.	PMID[15104493]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	leaves	Soorkesh Valley, Gollestan, Iran	n.a.	PMID[15104493]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	Hairy roots	n.a.	n.a.	PMID[19271765]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26285573]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27116034]
NPO6165	Prunus salicina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28202328]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29667821]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6619887]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6631435]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264679]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264682]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320741]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9380	Catharanthus ovalis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13459	Nitraria tangutorum	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13459	Nitraria tangutorum	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6165	Prunus salicina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9380	Catharanthus ovalis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13459	Nitraria tangutorum	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9380	Catharanthus ovalis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6165	Prunus salicina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6165	Prunus salicina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13459	Nitraria tangutorum	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6165	Prunus salicina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5881	Catharanthus roseus	Species	Apocynaceae	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
EC50	1

Activity Type	# Activity
Organism	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
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	EC50	=	20100.0	nM	PMID[30234295]

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 NPC238376 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	19727
0.1-0.2	26503
0.2-0.3	2626
0.3-0.4	548
0.4-0.5	284
0.5-0.6	115
0.6-0.7	35
0.7-0.8	0
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8824	High Similarity	NPC108831
0.8824	High Similarity	NPC182634
0.8429	Intermediate Similarity	NPC277205
0.8429	Intermediate Similarity	NPC37919
0.8289	Intermediate Similarity	NPC67105
0.7778	Intermediate Similarity	NPC19709
0.7568	Intermediate Similarity	NPC271692
0.7432	Intermediate Similarity	NPC323593
0.7432	Intermediate Similarity	NPC203500
0.7375	Intermediate Similarity	NPC227508
0.7179	Intermediate Similarity	NPC605784
0.7067	Intermediate Similarity	NPC249281
0.6933	Remote Similarity	NPC473043
0.6933	Remote Similarity	NPC331652
0.6923	Remote Similarity	NPC285197
0.6883	Remote Similarity	NPC46420
0.6753	Remote Similarity	NPC158674
0.6667	Remote Similarity	NPC210073
0.6667	Remote Similarity	NPC87125
0.6667	Remote Similarity	NPC601586
0.6625	Remote Similarity	NPC486578
0.6623	Remote Similarity	NPC476405
0.6548	Remote Similarity	NPC275454
0.6543	Remote Similarity	NPC116458
0.6543	Remote Similarity	NPC246943
0.6538	Remote Similarity	NPC136042
0.6538	Remote Similarity	NPC189142
0.6538	Remote Similarity	NPC77660
0.65	Remote Similarity	NPC307938
0.6463	Remote Similarity	NPC276377
0.6456	Remote Similarity	NPC245014
0.6456	Remote Similarity	NPC84362
0.6375	Remote Similarity	NPC117260
0.6296	Remote Similarity	NPC611303
0.6265	Remote Similarity	NPC190003
0.6207	Remote Similarity	NPC186816
0.6203	Remote Similarity	NPC127546
0.6203	Remote Similarity	NPC57625
0.6203	Remote Similarity	NPC173637
0.6203	Remote Similarity	NPC317489
0.6203	Remote Similarity	NPC223424
0.6203	Remote Similarity	NPC600591
0.6125	Remote Similarity	NPC609879
0.6092	Remote Similarity	NPC150164
0.6049	Remote Similarity	NPC27640
0.6044	Remote Similarity	NPC80068
0.6023	Remote Similarity	NPC115674
0.5977	Remote Similarity	NPC44931
0.5976	Remote Similarity	NPC59534
0.593	Remote Similarity	NPC251417
0.5926	Remote Similarity	NPC282987
0.5926	Remote Similarity	NPC297987
0.5914	Remote Similarity	NPC135358
0.5909	Remote Similarity	NPC233994
0.5889	Remote Similarity	NPC65711
0.5854	Remote Similarity	NPC305811
0.5851	Remote Similarity	NPC14187
0.5824	Remote Similarity	NPC32641
0.5824	Remote Similarity	NPC256188
0.5824	Remote Similarity	NPC72016
0.5824	Remote Similarity	NPC35119
0.5802	Remote Similarity	NPC39360
0.5802	Remote Similarity	NPC29763
0.5802	Remote Similarity	NPC210003
0.5802	Remote Similarity	NPC348541
0.5773	Remote Similarity	NPC480441
0.5714	Remote Similarity	NPC211532
0.5714	Remote Similarity	NPC143799
0.5714	Remote Similarity	NPC488364
0.5714	Remote Similarity	NPC605755
0.5682	Remote Similarity	NPC187379
0.5679	Remote Similarity	NPC111929
0.5679	Remote Similarity	NPC320283
0.5679	Remote Similarity	NPC41121
0.5679	Remote Similarity	NPC160515
0.567	Remote Similarity	NPC480796
0.5663	Remote Similarity	NPC84265
0.5652	Remote Similarity	NPC139060
0.5652	Remote Similarity	NPC229409
0.5632	Remote Similarity	NPC265115
0.561	Remote Similarity	NPC289667
0.5595	Remote Similarity	NPC27942
0.5568	Remote Similarity	NPC8856
0.5556	Remote Similarity	NPC22062
0.5556	Remote Similarity	NPC473634
0.5556	Remote Similarity	NPC138811
0.5506	Remote Similarity	NPC480466
0.5488	Remote Similarity	NPC135599
0.5488	Remote Similarity	NPC73855
0.5488	Remote Similarity	NPC113968
0.5488	Remote Similarity	NPC328940
0.5488	Remote Similarity	NPC277174
0.5488	Remote Similarity	NPC606877
0.5484	Remote Similarity	NPC209296
0.5484	Remote Similarity	NPC606657
0.5465	Remote Similarity	NPC197285
0.5465	Remote Similarity	NPC601144
0.5455	Remote Similarity	NPC477848
0.5426	Remote Similarity	NPC486577
0.5422	Remote Similarity	NPC261866
0.5412	Remote Similarity	NPC21100
0.5405	Remote Similarity	NPC252933
0.5402	Remote Similarity	NPC311830
0.5385	Remote Similarity	NPC203259
0.5385	Remote Similarity	NPC65003
0.5385	Remote Similarity	NPC33054
0.5385	Remote Similarity	NPC176740
0.5385	Remote Similarity	NPC471725
0.5385	Remote Similarity	NPC134532
0.5385	Remote Similarity	NPC602582
0.5357	Remote Similarity	NPC95090
0.5357	Remote Similarity	NPC27408
0.5352	Remote Similarity	NPC152042
0.5349	Remote Similarity	NPC20505
0.5342	Remote Similarity	NPC200740
0.53	Remote Similarity	NPC25523
0.5294	Remote Similarity	NPC181712
0.5294	Remote Similarity	NPC349108
0.5287	Remote Similarity	NPC22832
0.5287	Remote Similarity	NPC243930
0.5269	Remote Similarity	NPC240306
0.5269	Remote Similarity	NPC64425
0.525	Remote Similarity	NPC473241
0.5227	Remote Similarity	NPC223747
0.5227	Remote Similarity	NPC607707
0.5213	Remote Similarity	NPC470443
0.5213	Remote Similarity	NPC483414
0.5213	Remote Similarity	NPC483415
0.5208	Remote Similarity	NPC188815
0.5204	Remote Similarity	NPC603856
0.5176	Remote Similarity	NPC145038
0.5176	Remote Similarity	NPC56077
0.5176	Remote Similarity	NPC281131
0.5176	Remote Similarity	NPC168822
0.5176	Remote Similarity	NPC253662
0.5176	Remote Similarity	NPC179950
0.5176	Remote Similarity	NPC88789
0.5176	Remote Similarity	NPC491374
0.5158	Remote Similarity	NPC483416
0.5155	Remote Similarity	NPC101636
0.5155	Remote Similarity	NPC298171
0.5135	Remote Similarity	NPC166753
0.5116	Remote Similarity	NPC58716
0.5116	Remote Similarity	NPC45638
0.5111	Remote Similarity	NPC116864
0.5111	Remote Similarity	NPC244776
0.5106	Remote Similarity	NPC126784
0.5106	Remote Similarity	NPC241423
0.5106	Remote Similarity	NPC64051
0.5104	Remote Similarity	NPC142142
0.5068	Remote Similarity	NPC188871
0.5059	Remote Similarity	NPC254306
0.5057	Remote Similarity	NPC201292
0.5057	Remote Similarity	NPC599850
0.5055	Remote Similarity	NPC254540
0.5055	Remote Similarity	NPC487212
0.5055	Remote Similarity	NPC606546
0.5054	Remote Similarity	NPC183672
0.5054	Remote Similarity	NPC303913
0.5054	Remote Similarity	NPC605592
0.5052	Remote Similarity	NPC195257
0.5052	Remote Similarity	NPC473073

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC238376 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5049
0.1-0.2	4045
0.2-0.3	44
0.3-0.4	5
0.4-0.5	3
0.5-0.6	3
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
0.6044	Remote Similarity	NPD7251	Phase 2
0.5484	Remote Similarity	NPD7054	Phase 4
0.5385	Remote Similarity	NPD6797	Phase 2
0.5152	Remote Similarity	NPD7808	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