NPASS Compound

Natural Product: NPC10721

Natural Product ID	NPC10721
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NFCYJOSYKJZRIJ-UHNTWSMTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2375790
PubChem CID	73351893
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 94 97 0 0 0 0 0 0 0 0999 V2000 10.0576 -0.7653 -1.8729 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9099 -0.7010 -0.8764 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6566 -1.2121 -1.5312 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4615 -1.1875 -0.6090 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1493 0.1939 -0.1263 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8350 1.1714 -1.2066 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6629 0.8337 -2.0625 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3679 0.7087 -1.3209 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9763 1.9640 -0.6046 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6605 1.7490 0.1122 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2950 2.7387 0.7933 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9742 0.5674 -0.0050 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2634 0.3928 0.6669 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7951 -0.9926 0.4524 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2745 -1.0316 0.2212 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7588 -2.4014 0.0933 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2818 -3.0774 -0.9133 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5541 -2.6560 -2.2757 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2319 -1.3464 -2.4692 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9489 -0.3019 -1.4295 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8386 -0.6817 -0.3185 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8382 -1.3931 -0.7884 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9838 -1.9888 -0.0106 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7098 -1.5606 -2.2342 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5752 -1.8152 -3.0814 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5053 -0.2332 -1.0401 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0920 1.1994 -0.8790 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2584 1.5617 -2.0973 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3279 1.4438 0.4123 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1090 1.7500 1.5030 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1807 2.9600 2.1076 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4675 3.8284 1.6021 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0250 3.2608 3.2730 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9926 4.4873 3.7607 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8034 4.9115 4.9381 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9016 2.2832 3.9237 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7562 -0.8641 -2.0334 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6303 -4.4947 -0.5386 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0093 -4.6177 -0.7477 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2446 -0.5222 1.7886 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0985 -1.2071 2.1164 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1876 -0.6659 2.9107 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0127 -1.0556 -1.3559 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2690 0.2219 -2.3315 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8562 -1.4742 -2.6877 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1999 -1.2590 0.0241 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8161 0.3866 -0.6071 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8599 -2.2527 -1.8732 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4580 -0.6052 -2.4335 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6175 -1.7037 -1.0716 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7525 -1.8090 0.2815 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3700 0.1925 0.6795 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0654 0.5805 0.3979 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7301 1.2182 -1.8833 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7728 2.1782 -0.7460 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5387 1.6876 -2.7846 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8939 -0.0456 -2.6807 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5776 0.4876 -2.0758 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3523 -0.1209 -0.5947 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9225 2.8484 -1.2699 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7585 2.1870 0.1514 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2339 -1.7328 -0.1475 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7506 -0.5777 1.1129 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6533 -2.9609 1.0481 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6604 -2.7873 -2.9619 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2677 -3.4286 -2.7122 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0843 -0.9655 -3.5055 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2928 0.6753 -1.8467 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7238 -0.4345 0.7204 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5179 -2.7561 -0.5972 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5783 -2.3616 0.9542 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7188 -1.1992 0.2385 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9498 1.8870 -0.9350 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9207 1.6700 -2.9712 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4444 0.8407 -2.2234 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8175 2.5787 -1.8925 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8008 2.3847 0.1793 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3637 5.2509 3.3191 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3888 4.1037 5.3769 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5382 5.6658 4.5496 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1760 5.4545 5.6771 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9867 1.3185 3.3801 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9289 2.7075 3.9897 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5704 2.0817 4.9634 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9266 -0.4807 -2.9340 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0659 -5.1906 -1.1958 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3965 -4.6956 0.5210 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5326 -4.4995 0.0774 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8083 -0.9868 1.2802 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4738 -0.9111 3.0947 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8909 -2.2999 2.0454 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6494 -0.5188 3.8957 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5506 -1.7354 2.9803 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0670 -0.0475 2.9561 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 2 0 10 12 1 0 13 12 1 6 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 22 24 1 0 24 25 2 0 20 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 33 36 1 0 26 37 1 6 17 38 1 0 38 39 1 0 14 40 1 0 40 41 1 0 40 42 1 0 29 13 1 0 40 13 1 0 26 15 1 0 24 19 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 14 62 1 6 15 63 1 1 16 64 1 0 18 65 1 0 18 66 1 0 19 67 1 6 20 68 1 6 21 69 1 0 23 70 1 0 23 71 1 0 23 72 1 0 27 73 1 1 28 74 1 0 28 75 1 0 28 76 1 0 29 77 1 6 34 78 1 0 35 79 1 0 35 80 1 0 35 81 1 0 36 82 1 0 36 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	NFCYJOSYKJZRIJ-UHNTWSMTSA-N
Standard InCHI	InChI=1S/C35H52O7/c1-8-10-11-12-13-14-15-16-28(37)42-35-30(33(35,6)7)27-19-24(20-36)18-25-26(17-22(4)29(25)38)34(27,40)23(5)31(35)41-32(39)21(3)9-2/h9,17,19,23,25-27,30-31,36,40H,8,10-16,18,20H2,1-7H3/b21-9+/t23-,25-,26-,27+,30-,31-,34+,35-/m1/s1
SMILES	CCCCCCCCCC(=O)O[C@]12[C@H]([C@@H]3C=C(C[C@@H]4[C@@H](C=C(C)C4=O)[C@]3([C@H](C)[C@H]1OC(=O)/C(=C/C)/C)O)CO)C2(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	584.37	Volume:	625.403 ? Van der Waals volume.
Dense:	0.934	LogP:	4.878 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.144 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.259 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	22.0
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:	0.125	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.157	Fsp³:	0.743
MCE-18:	76.82 ? 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:	0.474	Fluc inhibitor:	0.014 ? 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:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.226	Promiscuous compounds:	0.437

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.235	MDCK Permeability:	-4.909
Pgp-inhibitor:	0.041	Pgp-substrate:	0.766
PAMPA:	0.592 ? 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):	0.845
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.976
Plasma Protein Binding (PPB):	98.539%	Volume Distribution (VD):	0.415
Fu:	1.646% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.91
OATP1B3 inhibitor:	0.975	BCRP inhibitor:	0.0
BSEP inhibitor:	0.97

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.074	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.952
CYP3A4-inhibitor:	0.167	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.722 ? 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):

5.954

Half-life (T1/2):

0.716

ADMET: Toxicity

hERG Blockers:	0.167	hERG Blockers (10um):	0.511
Human Hepatotoxicity (H-HT):	0.626	Drug-induced Liver Injury (DILI):	0.64
AMES Toxicity:	0.535	Rat Oral Acute Toxicity:	0.372
Maximum Recommended Daily Dose:	0.504	Skin Sensitization:	0.998
Carcinogencity:	0.876	Eye Corrosion:	0.028
Eye Irritation:	0.63	Respiratory Toxicity:	0.839
Drug-induced Neurotoxicity:	0.283	Ototoxicity:	0.554
Hematotoxicity:	0.688	Drug-induced Nephrotoxicity:	0.865
Genotoxicity:	0.017	RPMI-8226 Immunitoxicity:	0.261
A549 Cytotoxicity:	0.819	Hek293 Cytotoxicity:	0.655
BCF:	1.701 ? 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:	4.973 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.441 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.849 ? 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	DrugMatrix in vitro pharmacology data

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 NPC10721 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	18716
0.1-0.2	28661
0.2-0.3	2317
0.3-0.4	53
0.4-0.5	58
0.5-0.6	21
0.6-0.7	20
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC154363
0.8235	Intermediate Similarity	NPC485737
0.8088	Intermediate Similarity	NPC234858
0.8088	Intermediate Similarity	NPC179207
0.7857	Intermediate Similarity	NPC471127
0.7857	Intermediate Similarity	NPC481525
0.7857	Intermediate Similarity	NPC481531
0.7067	Intermediate Similarity	NPC600005
0.7	Intermediate Similarity	NPC482406
0.6883	Remote Similarity	NPC472759
0.6875	Remote Similarity	NPC140021
0.6835	Remote Similarity	NPC611138
0.6806	Remote Similarity	NPC472757
0.6806	Remote Similarity	NPC481522
0.6757	Remote Similarity	NPC485734
0.6712	Remote Similarity	NPC481520
0.6622	Remote Similarity	NPC482405
0.6447	Remote Similarity	NPC481528
0.6447	Remote Similarity	NPC476111
0.642	Remote Similarity	NPC482219
0.641	Remote Similarity	NPC236918
0.641	Remote Similarity	NPC156745
0.6364	Remote Similarity	NPC90814
0.6364	Remote Similarity	NPC189393
0.6364	Remote Similarity	NPC608501
0.625	Remote Similarity	NPC482221
0.6173	Remote Similarity	NPC482220
0.6104	Remote Similarity	NPC275696
0.6104	Remote Similarity	NPC255081
0.5904	Remote Similarity	NPC482222
0.5844	Remote Similarity	NPC157252
0.5823	Remote Similarity	NPC5991
0.5823	Remote Similarity	NPC196500
0.5823	Remote Similarity	NPC471108
0.5823	Remote Similarity	NPC5989
0.5802	Remote Similarity	NPC22628
0.5783	Remote Similarity	NPC481523
0.5714	Remote Similarity	NPC329080
0.5696	Remote Similarity	NPC145182
0.5556	Remote Similarity	NPC471126
0.5488	Remote Similarity	NPC484252
0.5432	Remote Similarity	NPC488610
0.5385	Remote Similarity	NPC171905
0.5349	Remote Similarity	NPC605007
0.5244	Remote Similarity	NPC486561
0.5222	Remote Similarity	NPC112752
0.5222	Remote Similarity	NPC311054
0.5181	Remote Similarity	NPC471128
0.5169	Remote Similarity	NPC138641
0.5169	Remote Similarity	NPC611243

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC10721 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6653
0.1-0.2	2444
0.2-0.3	50
0.3-0.4	3
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