NPASS Compound

Natural Product: NPC604195

Natural Product ID	NPC604195
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CHCBSUXEBKZFGJ-RLCKCSFISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL4530118
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 102106 0 0 0 0 0 0 0 0999 V2000 6.3567 -2.3795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2077 -1.4153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4681 0.0619 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7981 -1.9284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 -0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 -1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4200 -3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6805 -4.7665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9410 -6.2437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7919 -7.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0524 -8.6851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4619 -9.1981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7224 -10.6753 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6110 -8.2339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0205 -8.7470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3505 -6.7567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0586 0.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3307 -0.3437 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4797 0.6205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9178 2.0112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6574 3.4884 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3597 2.4247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8016 2.8381 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4215 1.9066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9361 2.1154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6386 3.7404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 4.7046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 6.1818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 6.1818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 6.6949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4095 7.9939 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3086 5.7307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0586 7.0297 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0481 4.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5481 4.2535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1620 4.1062 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8296 3.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0900 5.2795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4996 5.7926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7600 7.2698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1696 7.7828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3186 6.8186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7282 7.3316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0582 5.3414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2072 4.3772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6486 4.8284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3209 -1.2304 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3926 -3.5286 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5058 -3.3437 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6132 0.1849 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6849 -2.1132 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 0.9642 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3114 -2.7335 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9856 -3.7279 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8972 -3.0288 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2033 -5.0270 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1577 -4.5060 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3824 -6.6949 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9033 -9.6493 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1319 -11.1884 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1696 -7.7828 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4996 -5.7926 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3286 -0.8886 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5703 -0.9671 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3185 -0.6231 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2240 0.9061 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6803 4.5855 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6712 1.6909 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1251 3.9062 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1645 4.2936 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8350 3.3485 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6503 1.3429 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9935 2.1379 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2247 2.3597 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 7.6590 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 7.6818 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5672 4.6930 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2388 6.3647 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3086 7.6590 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 9.2929 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7702 5.3933 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5586 7.0297 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9434 2.7571 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4509 5.4514 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4895 2.7762 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 2.8381 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0671 6.3766 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6110 8.2339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4300 9.2600 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8772 6.3675 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9468 2.9000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3882 3.3512 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 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 13 14 1 0 14 15 2 0 15 16 1 0 15 17 1 0 17 18 1 0 17 19 2 0 8 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 25 27 1 0 27 28 1 0 25 29 1 0 29 30 1 0 20 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 37 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 31 43 1 0 43 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 52 53 1 0 52 54 1 0 54 55 1 0 54 56 2 0 43 6 1 0 56 49 1 0 19 12 1 0 29 22 1 0 41 33 1 0 1 57 1 0 1 58 1 0 1 59 1 0 5 60 1 0 5 61 1 0 6 62 1 6 8 63 1 6 10 64 1 0 10 65 1 0 11 66 1 0 11 67 1 0 13 68 1 0 14 69 1 0 16 70 1 0 18 71 1 0 19 72 1 0 20 73 1 1 22 74 1 1 24 75 1 0 24 76 1 0 26 77 1 0 27 78 1 0 27 79 1 0 28 80 1 0 29 81 1 6 30 82 1 0 31 83 1 6 33 84 1 6 35 85 1 1 36 86 1 0 36 87 1 0 36 88 1 0 37 89 1 6 38 90 1 0 39 91 1 1 40 92 1 0 41 93 1 1 42 94 1 0 43 95 1 1 47 96 1 0 48 97 1 0 50 98 1 0 51 99 1 0 53100 1 0 55101 1 0 56102 1 0 M END

Standard InCHIKey	CHCBSUXEBKZFGJ-RLCKCSFISA-N
Standard InCHI	InChI=1S/C36H46O20/c1-16-26(44)27(45)28(46)33(52-16)55-30-29(54-25(43)8-5-18-3-6-20(39)22(41)11-18)24(13-50-17(2)38)53-34(49-10-9-19-4-7-21(40)23(42)12-19)31(30)56-35-32(47)36(48,14-37)15-51-35/h3-8,11-12,16,24,26-35,37,39-42,44-48H,9-10,13-15H2,1-2H3/b8-5+/t16-,24+,26-,27+,28+,29+,30-,31+,32-,33-,34+,35-,36+/m0/s1
SMILES	CC(=O)OC[C@H]1O[C@@H](OCCc2ccc(O)c(O)c2)[C@H](O[C@@H]2OC[C@](O)(CO)[C@H]2O)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[C@@H]1OC(=O)/C=C/c1ccc(O)c(O)c1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	798.26	Volume:	740.506 ? Van der Waals volume.
Dense:	1.078	LogP:	0.765 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.143 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.964 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	32.0
TPSA:	310.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.056	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.447	Fsp³:	0.556
MCE-18:	133.0 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.697	Fluc inhibitor:	0.655 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.057 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.553 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.201	Promiscuous compounds:	0.513

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.365	MDCK Permeability:	-5.329
Pgp-inhibitor:	0.0	Pgp-substrate:	0.057
PAMPA:	1.0 ? 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):	0.735
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.06
Plasma Protein Binding (PPB):	62.429%	Volume Distribution (VD):	-0.408
Fu:	34.068% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.041
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.006 ? 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):

2.11

Half-life (T1/2):

3.367

ADMET: Toxicity

hERG Blockers:	0.026	hERG Blockers (10um):	0.533
Human Hepatotoxicity (H-HT):	0.312	Drug-induced Liver Injury (DILI):	0.608
AMES Toxicity:	0.931	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.018	Skin Sensitization:	1.0
Carcinogencity:	0.028	Eye Corrosion:	0.0
Eye Irritation:	0.074	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.996
Hematotoxicity:	0.022	Drug-induced Nephrotoxicity:	0.218
Genotoxicity:	0.446	RPMI-8226 Immunitoxicity:	0.019
A549 Cytotoxicity:	0.95	Hek293 Cytotoxicity:	0.36
BCF:	0.596 ? 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:	3.403 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.09 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.513 ? 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
NPO6610	Markhamia lutea	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599250]
NPO22788	Barnettia kerrii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6610	Markhamia lutea	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11625	Markhamia stipulata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11625	Markhamia stipulata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22788	Barnettia kerrii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6610	Markhamia lutea	Species	Bignoniaceae	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
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT325	Individual protein	Cyclooxygenase-2	Ovis aries	IC50	=	16000.0	nM	PMID[31255927]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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 NPC604195 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	14807
0.1-0.2	31134
0.2-0.3	3420
0.3-0.4	393
0.4-0.5	44
0.5-0.6	30
0.6-0.7	18
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC196063
0.8444	Intermediate Similarity	NPC610636
0.7396	Intermediate Similarity	NPC300894
0.7396	Intermediate Similarity	NPC23845
0.732	Intermediate Similarity	NPC141455
0.7263	Intermediate Similarity	NPC119537
0.7222	Intermediate Similarity	NPC40305
0.7158	Intermediate Similarity	NPC105005
0.7097	Intermediate Similarity	NPC611289
0.6458	Remote Similarity	NPC76406
0.6408	Remote Similarity	NPC476375
0.6408	Remote Similarity	NPC106818
0.6389	Remote Similarity	NPC188393
0.6344	Remote Similarity	NPC475530
0.6316	Remote Similarity	NPC328273
0.63	Remote Similarity	NPC205864
0.63	Remote Similarity	NPC298257
0.63	Remote Similarity	NPC247032
0.63	Remote Similarity	NPC175214
0.6296	Remote Similarity	NPC229505
0.625	Remote Similarity	NPC472350
0.625	Remote Similarity	NPC197316
0.625	Remote Similarity	NPC89105
0.6168	Remote Similarity	NPC87403
0.6132	Remote Similarity	NPC476378
0.6078	Remote Similarity	NPC296954
0.602	Remote Similarity	NPC68092
0.5979	Remote Similarity	NPC321638
0.5938	Remote Similarity	NPC81515
0.5895	Remote Similarity	NPC473799
0.5882	Remote Similarity	NPC269141
0.5872	Remote Similarity	NPC470934
0.5816	Remote Similarity	NPC171134
0.5743	Remote Similarity	NPC476377
0.5657	Remote Similarity	NPC64141
0.5586	Remote Similarity	NPC64195
0.5524	Remote Similarity	NPC252292
0.5505	Remote Similarity	NPC476384
0.5472	Remote Similarity	NPC112
0.5421	Remote Similarity	NPC100998
0.54	Remote Similarity	NPC46137
0.5392	Remote Similarity	NPC222433
0.5392	Remote Similarity	NPC321184
0.537	Remote Similarity	NPC96795
0.537	Remote Similarity	NPC264632
0.5319	Remote Similarity	NPC287597
0.5268	Remote Similarity	NPC476380
0.5238	Remote Similarity	NPC47471
0.5158	Remote Similarity	NPC473924
0.5149	Remote Similarity	NPC260425
0.5146	Remote Similarity	NPC483705
0.5133	Remote Similarity	NPC476381
0.5094	Remote Similarity	NPC263829
0.5052	Remote Similarity	NPC34293
0.5049	Remote Similarity	NPC483706
0.5049	Remote Similarity	NPC205195
0.5045	Remote Similarity	NPC259347

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC604195 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5457
0.1-0.2	3636
0.2-0.3	54
0.3-0.4	2
0.4-0.5	0
0.5-0.6	0
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
0.625	Remote Similarity	NPD7266	Phase 2

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