NPASS Compound

Natural Product: NPC320734

Natural Product ID	NPC320734
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Caseargrewiin B
IUPAC Name	[(1S,3R,5R,6aS,7S,8S,9R,10R,10aS)-1,3-diacetyloxy-10-hydroxy-9-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-7,8-dimethyl-7-[(2Z)-3-methylpenta-2,4-dienyl]-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] butanoate
Synonyms	Caseargrewiin B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL502864
PubChem CID	11787194
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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 -7.3833 -2.1943 -4.7273 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9398 -2.0220 -4.2715 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9449 -1.8090 -2.7762 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5446 -1.6383 -2.3140 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5780 -1.6837 -3.1494 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1820 -1.4253 -0.9991 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8845 -1.2632 -0.5415 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6694 0.1079 0.1618 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2177 0.1820 0.4091 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5623 1.5366 0.3046 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9113 1.3826 0.3982 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4864 0.2511 1.1458 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7003 -1.0030 1.2779 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7689 -0.6746 1.4937 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9729 -0.4351 2.9136 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5504 -1.6962 3.4623 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9257 -2.6840 2.5703 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5536 -1.9760 1.4110 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4762 -2.2354 0.5255 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7535 -3.6701 3.1305 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4115 -5.0133 3.1667 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2997 -5.3252 2.6640 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2347 -6.0848 3.7380 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1768 0.4834 3.5847 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6918 1.3111 4.5945 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9226 1.1656 4.8508 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1524 2.2977 5.3192 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7933 -1.8713 0.2277 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7950 0.0058 0.6560 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9633 0.1901 1.3402 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8985 0.6113 2.4977 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2813 -0.0943 0.7493 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3896 -0.5452 -0.4856 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6642 -0.8339 -1.0940 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8558 -0.6716 -0.4576 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0540 -0.9728 -1.1125 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0428 -1.4347 -2.4025 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8341 -1.5985 -3.0462 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6653 -1.3010 -2.3966 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2406 -1.7183 -3.0089 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6021 2.6477 0.8860 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1601 2.5304 1.2430 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8335 2.0167 -1.1361 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2682 3.3287 -1.4336 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0706 4.3020 -1.7968 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5207 4.0433 -1.8957 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5539 5.6186 -2.0992 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2518 6.6610 -2.4702 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6425 -1.3768 -5.4332 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4452 -3.1910 -5.2079 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0682 -2.1934 -3.8723 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5017 -1.1097 -4.7255 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3196 -2.8981 -4.5062 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5859 -0.9540 -2.4831 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3236 -2.7582 -2.3199 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1286 -1.3182 -1.3420 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2800 -0.0288 1.1085 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1667 0.9160 -0.3536 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7459 -0.3159 -0.5307 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2995 1.2770 -0.6668 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6823 0.6276 2.1997 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0501 -1.5117 2.1986 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0017 -0.3566 3.3065 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0211 -3.1889 2.1986 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9773 -3.1861 0.5472 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2802 -5.7220 3.8253 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2459 -7.0076 3.1214 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9181 -6.3861 4.7573 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0165 3.3238 4.9229 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2515 2.3273 6.3728 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2037 2.0047 5.3696 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0769 -2.2009 -0.1250 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1469 0.0832 1.3705 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4458 -0.6918 -1.0360 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9107 -0.3118 0.5544 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9802 -0.8238 -0.5516 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8450 -1.9678 -4.0728 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7354 -1.4502 -2.9542 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9604 -2.3088 -2.6053 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9285 2.4392 1.9434 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9369 3.5163 0.9741 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5421 2.8346 0.3316 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1770 2.1852 1.5215 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3270 3.5351 0.7481 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5474 2.7716 2.1256 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3129 1.3002 -1.8519 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8720 1.9639 -1.4311 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7928 3.5684 -1.3829 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9667 3.6063 -0.9724 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1321 4.9042 -2.1717 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6328 3.3059 -2.7501 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5433 5.7255 -1.9981 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3136 6.6486 -2.5930 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7516 7.5946 -2.6682 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 2 0 4 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 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 17 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 15 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 13 28 1 0 12 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 2 3 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 37 40 1 0 11 41 1 0 10 42 1 0 10 43 1 0 43 44 1 0 44 45 2 3 45 46 1 0 45 47 1 0 47 48 2 0 19 7 1 0 14 9 1 0 18 14 1 0 39 34 1 0 1 49 1 0 1 50 1 0 1 51 1 0 2 52 1 0 2 53 1 0 3 54 1 0 3 55 1 0 7 56 1 0 8 57 1 0 8 58 1 0 9 59 1 0 11 60 1 0 12 61 1 0 13 62 1 0 15 63 1 0 17 64 1 0 19 65 1 0 23 66 1 0 23 67 1 0 23 68 1 0 27 69 1 0 27 70 1 0 27 71 1 0 28 72 1 0 32 73 1 0 33 74 1 0 35 75 1 0 36 76 1 0 38 77 1 0 39 78 1 0 40 79 1 0 41 80 1 0 41 81 1 0 41 82 1 0 42 83 1 0 42 84 1 0 42 85 1 0 43 86 1 0 43 87 1 0 44 88 1 0 46 89 1 0 46 90 1 0 46 91 1 0 47 92 1 0 48 93 1 0 48 94 1 0 M END

Standard InCHIKey	YJKQLKAAMAXUDU-LRBOKHHASA-N
Standard InCHI	InChI=1S/C37H46O11/c1-8-10-30(41)46-27-19-28-34(44-23(5)38)48-35(45-24(6)39)37(28)29(20-27)36(7,18-17-21(3)9-2)22(4)32(33(37)43)47-31(42)16-13-25-11-14-26(40)15-12-25/h9,11-17,19,22,27,29,32-35,40,43H,2,8,10,18,20H2,1,3-7H3/b16-13+,21-17-/t22-,27+,29+,32-,33+,34+,35-,36-,37-/m1/s1
SMILES	CCCC(=O)OC1CC2C(C(C(C(C23C(OC(C3=C1)OC(=O)C)OC(=O)C)O)OC(=O)C=CC4=CC=C(C=C4)O)C)(C)CC=C(C)C=C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	666.3	Volume:	681.974 ? Van der Waals volume.
Dense:	0.977	LogP:	4.465 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.674 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.944 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	28.0
TPSA:	154.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.104	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.915	Fsp³:	0.514
MCE-18:	143.786 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.979	Fluc inhibitor:	0.199 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.521 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.18	Promiscuous compounds:	0.021

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.358	MDCK Permeability:	-4.911
Pgp-inhibitor:	0.044	Pgp-substrate:	0.869
PAMPA:	0.812 ? 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):	0.094
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.998
Plasma Protein Binding (PPB):	72.972%	Volume Distribution (VD):	-0.008
Fu:	23.78% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.778
OATP1B3 inhibitor:	0.976	BCRP inhibitor:	0.054
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.352
CYP2C19-inhibitor:	0.004	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.989 ? 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):

4.594

Half-life (T1/2):

1.166

ADMET: Toxicity

hERG Blockers:	0.055	hERG Blockers (10um):	0.529
Human Hepatotoxicity (H-HT):	0.562	Drug-induced Liver Injury (DILI):	0.56
AMES Toxicity:	0.875	Rat Oral Acute Toxicity:	0.733
Maximum Recommended Daily Dose:	0.986	Skin Sensitization:	0.994
Carcinogencity:	0.269	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.023
Drug-induced Neurotoxicity:	0.938	Ototoxicity:	0.903
Hematotoxicity:	0.043	Drug-induced Nephrotoxicity:	0.907
Genotoxicity:	0.986	RPMI-8226 Immunitoxicity:	0.32
A549 Cytotoxicity:	0.517	Hek293 Cytotoxicity:	0.928
BCF:	0.687 ? 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:	3.782 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.7 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.003 ? 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
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	n.a.	bark	n.a.	PMID[15730240]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	bark	in the campus of Khon Kaen University, Khon Kaen, Thailand	2001-SEP	PMID[15730240]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17567069]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26516994]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	4
MIC	1

Activity Type	# Activity
Cell line	2
Organism	2
Non-molecular	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
NPT91	Cell line	KB	Homo sapiens	IC50	=	2.3	ug.mL-1	PMID[15730240]
NPT639	Cell line	NCI-H187	Homo sapiens	IC50	=	1.5	ug.mL-1	PMID[15730240]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	12.5	ug.mL-1	PMID[15730240]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	1.9	ug.mL-1	PMID[15730240]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	2.4	ug.mL-1	PMID[15730240]

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 NPC320734 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	9279
0.1-0.2	37732
0.2-0.3	2563
0.3-0.4	205
0.4-0.5	35
0.5-0.6	35
0.6-0.7	6
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
0.7471	Intermediate Similarity	NPC481026
0.7191	Intermediate Similarity	NPC481025
0.6543	Remote Similarity	NPC316974
0.6364	Remote Similarity	NPC116292
0.6341	Remote Similarity	NPC201880
0.6118	Remote Similarity	NPC488964
0.6118	Remote Similarity	NPC184512
0.6071	Remote Similarity	NPC609715
0.5952	Remote Similarity	NPC134270
0.5882	Remote Similarity	NPC217921
0.5882	Remote Similarity	NPC135015
0.5783	Remote Similarity	NPC602188
0.5765	Remote Similarity	NPC81567
0.5765	Remote Similarity	NPC488652
0.5761	Remote Similarity	NPC162569
0.5761	Remote Similarity	NPC35160
0.5747	Remote Similarity	NPC252296
0.5698	Remote Similarity	NPC330003
0.5698	Remote Similarity	NPC470321
0.5698	Remote Similarity	NPC264867
0.5698	Remote Similarity	NPC473207
0.5591	Remote Similarity	NPC230331
0.5581	Remote Similarity	NPC329623
0.5581	Remote Similarity	NPC609711
0.5532	Remote Similarity	NPC486751
0.5412	Remote Similarity	NPC488659
0.5412	Remote Similarity	NPC604149
0.5402	Remote Similarity	NPC488654
0.5376	Remote Similarity	NPC208293
0.5341	Remote Similarity	NPC488658
0.5341	Remote Similarity	NPC488655
0.5333	Remote Similarity	NPC119550
0.5275	Remote Similarity	NPC40728
0.5263	Remote Similarity	NPC267469
0.5227	Remote Similarity	NPC311223
0.5227	Remote Similarity	NPC128795
0.5227	Remote Similarity	NPC488660
0.5227	Remote Similarity	NPC488657
0.5227	Remote Similarity	NPC609880
0.5208	Remote Similarity	NPC109376
0.5158	Remote Similarity	NPC87630
0.5057	Remote Similarity	NPC88507
0.5056	Remote Similarity	NPC7644

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC320734 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4974
0.1-0.2	4146
0.2-0.3	30
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