NPASS Compound

Natural Product: NPC275696

Natural Product ID	NPC275696
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PSBLORXWXFKGFT-WVMKKHFXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2375783
PubChem CID	500522
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 [CHEMONTID:0002906] Phorbol esters

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 94 97 0 0 0 0 0 0 0 0999 V2000 11.0750 -1.7985 -1.6624 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6300 -2.2195 -1.3634 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1199 -1.2574 -0.3133 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7076 -1.5257 0.0990 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7227 -1.4363 -1.0162 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6905 -0.0762 -1.6702 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3295 1.0325 -0.7433 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9842 0.8915 -0.1099 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8842 0.8429 -1.1227 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5246 0.7028 -0.5243 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2286 1.8602 0.3752 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8643 1.7498 0.9954 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4180 2.6214 1.7627 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0299 0.7178 0.7752 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2564 0.4310 1.2366 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8879 -0.8796 0.7932 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3492 -0.7311 0.5770 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9806 -1.9460 0.0016 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2826 -2.1556 -0.1226 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3980 -1.2510 0.2729 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0744 0.1283 -0.2604 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8631 0.2382 -1.0785 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1770 1.2849 -2.0603 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4845 1.3565 -2.1897 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2787 2.2774 -3.0800 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1382 0.3845 -1.3133 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2805 -0.1196 -1.3927 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5558 0.3791 -0.4192 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2392 1.6482 0.2507 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7003 2.7097 -0.7199 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2975 1.4900 1.4354 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0387 1.3540 2.6322 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0870 2.2785 3.6325 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4433 3.3398 3.5250 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9122 1.9919 4.8315 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5663 0.1755 -1.4149 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2752 1.1164 0.6800 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6794 -3.4653 -0.7372 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5469 -4.1808 -1.0448 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2530 -0.8264 2.1232 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0595 -1.6245 2.1960 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0239 -0.8645 3.3935 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6646 -2.0606 -0.7490 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1583 -0.7096 -1.8080 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4616 -2.3113 -2.5520 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0472 -2.2252 -2.2831 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6931 -3.2559 -0.9785 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7602 -1.4331 0.5976 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2949 -0.2027 -0.6012 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6596 -2.5790 0.4889 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4698 -0.8799 0.9541 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9765 -2.1804 -1.7934 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7265 -1.7304 -0.6116 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0513 -0.0538 -2.5517 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7344 0.1197 -2.0295 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4369 1.9829 -1.2718 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0806 1.0663 0.1000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0115 -0.0243 0.5280 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8722 1.7496 0.6042 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1265 0.0284 -1.8360 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9222 1.7833 -1.7163 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7453 0.5091 -1.2761 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5475 -0.2170 0.1245 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9359 1.8205 1.2312 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2447 2.8320 -0.1584 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3554 -1.3481 -0.0651 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9369 -0.4636 1.4728 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3653 -2.7457 -0.3554 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3275 -1.1626 1.3966 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3640 -1.6397 -0.0382 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8052 -0.7194 -1.6872 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5116 1.9420 -2.6346 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1941 1.7474 -3.4212 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6741 2.5802 -3.9602 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6144 3.1466 -2.4825 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1656 2.0987 0.6625 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4609 3.4376 -1.0068 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7881 3.1511 -0.2653 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3346 2.1696 -1.6390 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7991 2.4731 1.5221 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3058 2.9076 5.3100 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2789 1.3919 5.5206 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7697 1.3209 4.5397 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9376 0.2808 -2.3067 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2440 1.2809 0.8306 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2430 -4.0149 0.0502 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3339 -3.2996 -1.6283 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5351 -5.0917 -0.6648 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6477 -1.3338 1.3066 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1111 -2.6944 2.2999 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6013 -1.1732 3.0785 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1282 -0.8643 3.2910 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8377 -1.8845 3.8512 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6471 -0.1664 4.1740 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 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 15 14 1 6 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 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 24 26 1 0 26 27 2 0 22 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 28 36 1 6 21 37 1 1 19 38 1 0 38 39 1 0 16 40 1 0 40 41 1 0 40 42 1 0 31 15 1 0 40 15 1 0 28 17 1 0 26 21 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 2 47 1 0 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 5 52 1 0 5 53 1 0 6 54 1 0 6 55 1 0 7 56 1 0 7 57 1 0 8 58 1 0 8 59 1 0 9 60 1 0 9 61 1 0 10 62 1 0 10 63 1 0 11 64 1 0 11 65 1 0 16 66 1 6 17 67 1 1 18 68 1 0 20 69 1 0 20 70 1 0 22 71 1 6 23 72 1 0 25 73 1 0 25 74 1 0 25 75 1 0 29 76 1 1 30 77 1 0 30 78 1 0 30 79 1 0 31 80 1 1 35 81 1 0 35 82 1 0 35 83 1 0 36 84 1 0 37 85 1 0 38 86 1 0 38 87 1 0 39 88 1 0 41 89 1 0 41 90 1 0 41 91 1 0 42 92 1 0 42 93 1 0 42 94 1 0 M END

Standard InCHIKey	PSBLORXWXFKGFT-WVMKKHFXSA-N
Standard InCHI	InChI=1S/C34H52O8/c1-7-8-9-10-11-12-13-14-15-16-27(37)42-34-28(31(34,5)6)25-18-24(20-35)19-32(39)26(17-21(2)29(32)38)33(25,40)22(3)30(34)41-23(4)36/h17-18,22,25-26,28,30,35,39-40H,7-16,19-20H2,1-6H3/t22-,25+,26-,28-,30-,32-,33-,34-/m1/s1
SMILES	CCCCCCCCCCCC(=O)O[C@]12[C@H]([C@@H]3C=C(C[C@]4([C@@H](C=C(C)C4=O)[C@]3([C@H](C)[C@H]1OC(=O)C)O)O)CO)C2(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	588.37	Volume:	619.534 ? Van der Waals volume.
Dense:	0.95	LogP:	4.642 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.109 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.801 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	21.0
TPSA:	130.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.156	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.967	Fsp³:	0.794
MCE-18:	79.148 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.346	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.219	Promiscuous compounds:	0.497

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.124	MDCK Permeability:	-4.666
Pgp-inhibitor:	0.313	Pgp-substrate:	0.98
PAMPA:	0.444 ? 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):	0.907
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.959
Plasma Protein Binding (PPB):	94.561%	Volume Distribution (VD):	0.482
Fu:	6.339% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.989
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.019
BSEP inhibitor:	0.843

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.106
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.234
CYP3A4-inhibitor:	0.029	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.044 ? 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):

4.279

Half-life (T1/2):

1.002

ADMET: Toxicity

hERG Blockers:	0.152	hERG Blockers (10um):	0.448
Human Hepatotoxicity (H-HT):	0.663	Drug-induced Liver Injury (DILI):	0.444
AMES Toxicity:	0.191	Rat Oral Acute Toxicity:	0.208
Maximum Recommended Daily Dose:	0.174	Skin Sensitization:	0.98
Carcinogencity:	0.307	Eye Corrosion:	0.063
Eye Irritation:	0.761	Respiratory Toxicity:	0.828
Drug-induced Neurotoxicity:	0.024	Ototoxicity:	0.557
Hematotoxicity:	0.568	Drug-induced Nephrotoxicity:	0.521
Genotoxicity:	0.002	RPMI-8226 Immunitoxicity:	0.087
A549 Cytotoxicity:	0.274	Hek293 Cytotoxicity:	0.131
BCF:	1.837 ? 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:	5.107 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.545 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.711 ? 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
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049973]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23701597]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25819096]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2978	Croton tiglium	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
IC50	1

Activity Type	# Activity
Cell line	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
NPT890	Cell line	SNU-387	Homo sapiens	IC50	>	10000.0	nM	PMID[23701597]

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 NPC275696 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	15406
0.1-0.2	31980
0.2-0.3	2278
0.3-0.4	53
0.4-0.5	60
0.5-0.6	35
0.6-0.7	23
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC255081
0.9206	High Similarity	NPC5991
0.9206	High Similarity	NPC196500
0.9206	High Similarity	NPC471108
0.9206	High Similarity	NPC5989
0.8788	High Similarity	NPC22628
0.8788	High Similarity	NPC600005
0.8413	Intermediate Similarity	NPC171905
0.8125	Intermediate Similarity	NPC472397
0.7879	Intermediate Similarity	NPC472758
0.7857	Intermediate Similarity	NPC484333
0.7467	Intermediate Similarity	NPC138641
0.7467	Intermediate Similarity	NPC611243
0.7353	Intermediate Similarity	NPC157252
0.7246	Intermediate Similarity	NPC471125
0.7143	Intermediate Similarity	NPC145182
0.7083	Intermediate Similarity	NPC243902
0.7051	Intermediate Similarity	NPC479001
0.7051	Intermediate Similarity	NPC479002
0.7027	Intermediate Similarity	NPC145238
0.6986	Remote Similarity	NPC478999
0.6957	Remote Similarity	NPC485736
0.6957	Remote Similarity	NPC277477
0.6957	Remote Similarity	NPC479003
0.6957	Remote Similarity	NPC485735
0.6944	Remote Similarity	NPC471128
0.6944	Remote Similarity	NPC471126
0.6883	Remote Similarity	NPC482199
0.6883	Remote Similarity	NPC482197
0.6806	Remote Similarity	NPC488610
0.68	Remote Similarity	NPC609983
0.6709	Remote Similarity	NPC482198
0.6585	Remote Similarity	NPC283875
0.6316	Remote Similarity	NPC488611
0.6267	Remote Similarity	NPC485732
0.6265	Remote Similarity	NPC601559
0.6216	Remote Similarity	NPC485737
0.6145	Remote Similarity	NPC601392
0.6133	Remote Similarity	NPC486561
0.6125	Remote Similarity	NPC472398
0.6125	Remote Similarity	NPC600915
0.6104	Remote Similarity	NPC10721
0.6	Remote Similarity	NPC22571
0.5974	Remote Similarity	NPC484252
0.5942	Remote Similarity	NPC153036
0.5921	Remote Similarity	NPC19464
0.5854	Remote Similarity	NPC469647
0.5854	Remote Similarity	NPC469648
0.5823	Remote Similarity	NPC607335
0.5823	Remote Similarity	NPC610849
0.5765	Remote Similarity	NPC601964
0.5714	Remote Similarity	NPC11410
0.5714	Remote Similarity	NPC600144
0.5634	Remote Similarity	NPC156252
0.56	Remote Similarity	NPC485733
0.5556	Remote Similarity	NPC158523
0.5455	Remote Similarity	NPC482454
0.5443	Remote Similarity	NPC477091
0.5422	Remote Similarity	NPC153651
0.5405	Remote Similarity	NPC71889
0.5405	Remote Similarity	NPC475937
0.5385	Remote Similarity	NPC17138
0.5385	Remote Similarity	NPC485734
0.5385	Remote Similarity	NPC101825
0.5385	Remote Similarity	NPC170212
0.5385	Remote Similarity	NPC215643
0.5385	Remote Similarity	NPC265499
0.5333	Remote Similarity	NPC482406
0.5316	Remote Similarity	NPC221511
0.5238	Remote Similarity	NPC472760
0.5195	Remote Similarity	NPC472757
0.5122	Remote Similarity	NPC151216
0.5122	Remote Similarity	NPC89227
0.5062	Remote Similarity	NPC485731
0.506	Remote Similarity	NPC479000
0.5059	Remote Similarity	NPC600879
0.5059	Remote Similarity	NPC605007
0.5057	Remote Similarity	NPC486562

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC275696 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6237
0.1-0.2	2859
0.2-0.3	54
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
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
		NPD

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