NPASS Compound

Natural Product: NPC67290

Natural Product ID	NPC67290
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SYXKKJDQNXPUSI-IFEMBOOLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL442897
PubChem CID	44575954
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane 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 83 86 0 0 0 0 0 0 0 0999 V2000 9.4204 2.0145 0.5007 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7311 1.2061 1.5795 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7479 0.2530 0.9820 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4585 -0.7033 0.0441 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4525 -1.6753 -0.5623 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8388 -2.4091 0.5585 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5629 -2.4237 0.8664 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5998 -1.6784 0.0873 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3069 -1.6676 0.3646 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3181 -0.9318 -0.3960 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6661 -0.2417 -1.3989 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9684 -0.9308 -0.0909 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0306 -0.2483 -0.7918 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1160 -0.9857 -1.3727 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1767 -0.9119 -0.5915 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8282 -0.1264 0.5712 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6700 -1.0849 1.6640 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3592 -2.5085 1.2557 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0460 -1.2184 2.3124 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1850 -1.3822 1.4226 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7725 -0.3927 0.5896 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1346 0.9540 0.4184 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7841 1.2032 -1.0324 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6587 1.7078 -1.4884 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8079 2.4454 -2.7842 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1272 2.4592 -3.2554 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1724 3.0449 -2.6038 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9663 3.6220 -1.5036 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5786 3.0355 -3.1420 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3247 1.6952 -0.9822 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8049 0.7458 0.0403 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0089 1.3648 0.9918 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1094 2.9871 -0.4056 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8432 0.8460 1.0812 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6104 1.5337 2.0174 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4886 -0.7849 1.8158 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6730 0.2762 2.8379 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7357 -1.6868 1.6903 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9905 -1.7035 -2.6995 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7229 2.1519 -0.3494 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6970 3.0176 0.9064 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3337 1.4806 0.1838 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1335 1.9551 2.1742 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4677 0.7182 2.2472 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0054 0.8501 0.4122 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2101 -0.3206 1.7365 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1601 -1.2932 0.6657 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0181 -0.1612 -0.7198 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0766 -2.4211 -1.1229 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7683 -1.1948 -1.2473 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5256 -2.9898 1.1809 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1868 -2.9924 1.7127 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8774 -1.0764 -0.7784 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9724 -2.2423 1.2100 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5245 0.2969 -1.6392 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1079 -1.4176 -0.9029 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9702 -0.7931 2.4692 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3027 -2.7929 1.4111 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9042 -3.2012 1.9337 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7299 -2.7386 0.2374 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0945 -0.4140 3.0782 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9828 -2.1570 2.9596 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2808 -2.4561 1.0449 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3075 -0.7022 -0.3465 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7953 1.7519 0.7934 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5773 0.9061 -1.6907 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1099 1.9674 -3.5037 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4475 3.4906 -2.6740 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6736 2.2671 -3.9313 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2131 2.6745 -2.2884 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9112 4.0327 -3.4364 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6343 1.7510 -1.8909 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4899 2.1264 0.5755 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0191 3.6692 -1.0970 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5244 0.0465 3.5306 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7872 0.6197 3.3692 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0514 1.1910 2.2839 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4024 -2.7181 1.4174 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3172 -1.6918 2.6187 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3437 -1.3225 0.8454 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9554 -2.1825 -2.9613 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6975 -0.9331 -3.4343 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1760 -2.4503 -2.5980 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 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 16 15 1 6 16 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 24 30 1 0 30 31 1 0 31 32 1 1 30 33 1 0 22 34 1 0 34 35 2 0 21 36 1 0 36 37 1 0 36 38 1 0 14 39 1 0 31 13 1 0 34 16 1 0 31 16 1 0 36 20 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 0 2 44 1 0 3 45 1 0 3 46 1 0 4 47 1 0 4 48 1 0 5 49 1 0 5 50 1 0 6 51 1 0 7 52 1 0 8 53 1 0 9 54 1 0 13 55 1 6 15 56 1 0 17 57 1 1 18 58 1 0 18 59 1 0 18 60 1 0 19 61 1 0 19 62 1 0 20 63 1 6 21 64 1 6 22 65 1 1 23 66 1 0 25 67 1 0 25 68 1 0 29 69 1 0 29 70 1 0 29 71 1 0 30 72 1 6 32 73 1 0 33 74 1 0 37 75 1 0 37 76 1 0 37 77 1 0 38 78 1 0 38 79 1 0 38 80 1 0 39 81 1 0 39 82 1 0 39 83 1 0 M END

Standard InCHIKey	SYXKKJDQNXPUSI-IFEMBOOLSA-N
Standard InCHI	InChI=1S/C32H44O7/c1-7-8-9-10-11-12-13-14-25(34)39-29-19(2)17-31-20(3)15-24-26(30(24,5)6)23(28(31)36)16-22(18-38-21(4)33)27(35)32(29,31)37/h11-14,16-17,20,23-24,26-27,29,35,37H,7-10,15,18H2,1-6H3/b12-11-,14-13+/t20-,23+,24-,26+,27-,29+,31+,32+/m1/s1
SMILES	CCCCC/C=CC=CC(=O)O[C@H]1C(=C[C@]23[C@H](C)C[C@@H]4[C@H]([C@H](C=C(COC(=O)C)[C@H]([C@]13O)O)C2=O)C4(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	540.31	Volume:	570.879 ? Van der Waals volume.
Dense:	0.946	LogP:	4.982 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.274 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.188 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	23.0
TPSA:	110.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.144	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.23	Fsp³:	0.656
MCE-18:	108.075 ? 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:	0.653	Fluc inhibitor:	0.082 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.117 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.212	Promiscuous compounds:	0.386

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.303	MDCK Permeability:	-5.0
Pgp-inhibitor:	0.902	Pgp-substrate:	0.044
PAMPA:	0.01 ? 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):	0.062
20% Bioavailability (F20%):	0.857	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031	MRP1:	0.374
Plasma Protein Binding (PPB):	95.978%	Volume Distribution (VD):	-0.12
Fu:	3.561% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.992	BCRP inhibitor:	0.009
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.782
CYP2C19-inhibitor:	0.009	CYP2C19-substrate:	0.214
CYP2C9-inhibitor:	0.063	CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.19
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.909 ? 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):

6.81

Half-life (T1/2):

0.867

ADMET: Toxicity

hERG Blockers:	0.15	hERG Blockers (10um):	0.453
Human Hepatotoxicity (H-HT):	0.524	Drug-induced Liver Injury (DILI):	0.112
AMES Toxicity:	0.486	Rat Oral Acute Toxicity:	0.195
Maximum Recommended Daily Dose:	0.637	Skin Sensitization:	0.999
Carcinogencity:	0.387	Eye Corrosion:	0.011
Eye Irritation:	0.556	Respiratory Toxicity:	0.359
Drug-induced Neurotoxicity:	0.026	Ototoxicity:	0.56
Hematotoxicity:	0.166	Drug-induced Nephrotoxicity:	0.846
Genotoxicity:	0.031	RPMI-8226 Immunitoxicity:	0.11
A549 Cytotoxicity:	0.435	Hek293 Cytotoxicity:	0.644
BCF:	1.81 ? 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:	5.042 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.857 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.408 ? 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
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[12350140]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[12762796]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387657]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[1955882]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[24660966]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29148766]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184480]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	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	1
IC50	2
CC50	1

Activity Type	# Activity
Cell line	2
Organism	1
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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	5100.0	nM	PMID[27246615]
NPT25	Cell line	MT4	Homo sapiens	CC50	>	900.0	nM	PMID[31184480]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	1.8	nM	PMID[31184480]
NPT2	Others	Unspecified	n.a.	Activity	>	75.0	%	PMID[12350140]

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 NPC67290 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	18032
0.1-0.2	28277
0.2-0.3	3428
0.3-0.4	81
0.4-0.5	7
0.5-0.6	14
0.6-0.7	7
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC133677
0.9545	High Similarity	NPC482242
0.9545	High Similarity	NPC482243
0.8116	Intermediate Similarity	NPC47951
0.7887	Intermediate Similarity	NPC46269
0.7887	Intermediate Similarity	NPC106395
0.7703	Intermediate Similarity	NPC75898
0.7703	Intermediate Similarity	NPC221349
0.6933	Remote Similarity	NPC138757
0.68	Remote Similarity	NPC123855
0.68	Remote Similarity	NPC76550
0.6711	Remote Similarity	NPC138303
0.6282	Remote Similarity	NPC482236
0.6234	Remote Similarity	NPC482240
0.6234	Remote Similarity	NPC482239
0.5867	Remote Similarity	NPC607683
0.5789	Remote Similarity	NPC308191
0.5789	Remote Similarity	NPC38423
0.5676	Remote Similarity	NPC600642
0.5616	Remote Similarity	NPC604048
0.56	Remote Similarity	NPC482234
0.56	Remote Similarity	NPC303053
0.5455	Remote Similarity	NPC257240
0.5357	Remote Similarity	NPC134131
0.5357	Remote Similarity	NPC25043
0.519	Remote Similarity	NPC92898
0.519	Remote Similarity	NPC31883
0.519	Remote Similarity	NPC179891
0.5056	Remote Similarity	NPC287311

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC67290 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6499
0.1-0.2	2573
0.2-0.3	77
0.3-0.4	0
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
0.5455	Remote Similarity	NPD6371	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