NPASS Compound

Natural Product: NPC49818

Natural Product ID	NPC49818
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FMIMFCRXYXVFTA-YUVMXPMLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	470665
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 79 83 0 0 0 0 0 0 0 0999 V2000 6.0101 -1.8875 -0.1365 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9993 -0.9707 0.5707 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9237 -1.4962 1.9971 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4958 0.4094 0.4773 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5417 1.5124 0.2447 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3782 1.0621 -0.5752 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3538 2.1396 -0.8064 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2243 2.1636 0.1736 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5152 0.8697 0.3931 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3413 0.6645 1.9016 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3575 -0.2711 -0.0682 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8817 -1.3323 -0.6819 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5549 -1.5298 -0.9942 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3462 -0.6009 -0.0612 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7991 -0.8279 -0.1448 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2613 -1.3197 -1.5223 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1460 -1.9921 0.7963 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5848 -2.2823 0.8694 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4843 -1.1676 0.5713 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6938 -1.3812 0.6388 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0746 0.2023 0.1937 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6627 0.5852 -1.1308 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7051 1.1357 1.2379 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6117 0.3409 0.3025 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1328 1.5687 -0.4181 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7565 1.8810 0.1430 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8294 0.7756 -0.3075 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5733 1.0362 -1.7785 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7866 -0.1141 0.2209 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6675 -1.2683 -0.0636 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8622 0.5999 -1.8896 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0710 0.6368 -2.1696 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9615 0.1226 -2.8152 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9501 -2.9174 0.2697 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0036 -1.4235 0.0048 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7840 -1.8441 -1.2217 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1298 -2.2943 2.0791 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8649 -1.9944 2.3077 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6100 -0.6853 2.6622 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3592 0.4978 -0.2491 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0062 0.6415 1.4671 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1158 1.8401 1.2395 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0886 2.3596 -0.2180 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0631 2.1719 -1.8580 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9135 3.1107 -0.6376 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6731 2.5077 1.1482 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5615 3.0028 -0.1305 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9091 -0.2214 2.2715 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7103 0.6553 2.2163 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8028 1.5289 2.4446 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5666 -2.1124 -0.9809 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6846 -1.2149 -2.0531 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8106 -2.5767 -0.8211 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9984 -0.9160 0.9671 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4703 -0.5041 -2.2111 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5270 -2.0637 -1.9076 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2098 -1.9220 -1.3964 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6369 -1.8281 1.7695 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6212 -2.8817 0.3434 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8235 -2.6285 1.9178 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8721 -3.1639 0.2275 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9348 -0.2976 -1.7645 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6453 1.1251 -0.9883 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0458 1.2435 -1.7393 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1175 2.0454 1.3847 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8764 0.5677 2.1978 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7229 1.4408 0.9058 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3624 0.5051 1.3927 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7600 2.4621 -0.2041 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0333 1.4646 -1.4967 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7853 2.0495 1.2186 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4440 2.8197 -0.4067 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5455 2.1552 -1.9327 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3337 0.5499 -2.1338 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3999 0.6854 -2.4280 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8773 0.1216 1.3215 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8343 -1.3340 -1.1625 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3118 -2.2363 0.3545 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1236 0.2438 -3.8163 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 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 1 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 11 29 1 0 29 30 1 0 6 31 1 6 31 32 2 0 31 33 1 0 30 2 1 0 29 6 1 0 27 9 1 0 27 14 1 0 24 15 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 5 42 1 0 5 43 1 0 7 44 1 0 7 45 1 0 8 46 1 0 8 47 1 0 10 48 1 0 10 49 1 0 10 50 1 0 12 51 1 0 13 52 1 0 13 53 1 0 14 54 1 0 16 55 1 0 16 56 1 0 16 57 1 0 17 58 1 0 17 59 1 0 18 60 1 0 18 61 1 0 22 62 1 0 22 63 1 0 22 64 1 0 23 65 1 0 23 66 1 0 23 67 1 0 24 68 1 0 25 69 1 0 25 70 1 0 26 71 1 0 26 72 1 0 28 73 1 0 28 74 1 0 28 75 1 0 29 76 1 0 30 77 1 0 30 78 1 0 33 79 1 0 M END

Standard InCHIKey	FMIMFCRXYXVFTA-YUVMXPMLSA-N
Standard InCHI	InChI=1S/C30H46O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-22H,9-18H2,1-7H3,(H,32,33)/t20?,21?,22?,27-,28+,29+,30-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CCC4[C@@]5(C)CCC(=O)C(C)(C)C5CC[C@@]34C)C2C1)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	454.34	Volume:	503.115 ? Van der Waals volume.
Dense:	0.903	LogP:	3.926 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.316 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.794 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	28.0
TPSA:	54.37 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.419	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.554	Fsp³:	0.867
MCE-18:	104.464 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.497	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:	0.015 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.533	Promiscuous compounds:	0.006

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.15	MDCK Permeability:	-4.932
Pgp-inhibitor:	0.003	Pgp-substrate:	0.0
PAMPA:	0.996 ? 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):	0.0
20% Bioavailability (F20%):	0.001	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.83

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.204	MRP1:	0.966
Plasma Protein Binding (PPB):	93.902%	Volume Distribution (VD):	-0.127
Fu:	6.502% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.991	BCRP inhibitor:	0.004
BSEP inhibitor:	0.97

ADMET: Metabolism

CYP1A2-inhibitor:	0.029	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.988	CYP2C19-substrate:	0.015
CYP2C9-inhibitor:	0.174	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.004	CYP2C8-inhibitor:	0.946
HLM stability:	0.647 ? 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):

3.487

Half-life (T1/2):

0.707

ADMET: Toxicity

hERG Blockers:	0.051	hERG Blockers (10um):	0.123
Human Hepatotoxicity (H-HT):	0.773	Drug-induced Liver Injury (DILI):	0.358
AMES Toxicity:	0.045	Rat Oral Acute Toxicity:	0.46
Maximum Recommended Daily Dose:	0.732	Skin Sensitization:	0.609
Carcinogencity:	0.759	Eye Corrosion:	0.004
Eye Irritation:	0.198	Respiratory Toxicity:	0.741
Drug-induced Neurotoxicity:	0.124	Ototoxicity:	0.725
Hematotoxicity:	0.157	Drug-induced Nephrotoxicity:	0.415
Genotoxicity:	0.582	RPMI-8226 Immunitoxicity:	0.024
A549 Cytotoxicity:	0.049	Hek293 Cytotoxicity:	0.214
BCF:	1.74 ? 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:	4.511 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.873 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.373 ? 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
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869194]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18588343]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19331340]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21070010]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21070010]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27700077]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28225280]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31789520]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31804070]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	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

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

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 NPC49818 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	27676
0.1-0.2	19000
0.2-0.3	2328
0.3-0.4	531
0.4-0.5	204
0.5-0.6	73
0.6-0.7	33
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8197	Intermediate Similarity	NPC158141
0.7705	Intermediate Similarity	NPC267691
0.7419	Intermediate Similarity	NPC274050
0.7419	Intermediate Similarity	NPC162632
0.7231	Intermediate Similarity	NPC291028
0.7213	Intermediate Similarity	NPC604575
0.7077	Intermediate Similarity	NPC38754
0.6857	Remote Similarity	NPC600880
0.6769	Remote Similarity	NPC480946
0.6769	Remote Similarity	NPC130577
0.6769	Remote Similarity	NPC142415
0.6769	Remote Similarity	NPC102683
0.6716	Remote Similarity	NPC200752
0.6716	Remote Similarity	NPC120840
0.6716	Remote Similarity	NPC298554
0.6667	Remote Similarity	NPC270768
0.6667	Remote Similarity	NPC59263
0.6667	Remote Similarity	NPC210106
0.6667	Remote Similarity	NPC93744
0.6667	Remote Similarity	NPC476888
0.6462	Remote Similarity	NPC280654
0.6418	Remote Similarity	NPC263272
0.6418	Remote Similarity	NPC84319
0.6418	Remote Similarity	NPC156981
0.6418	Remote Similarity	NPC52021
0.6418	Remote Similarity	NPC599947
0.6324	Remote Similarity	NPC231063
0.6324	Remote Similarity	NPC282395
0.6324	Remote Similarity	NPC110308
0.6232	Remote Similarity	NPC173089
0.6232	Remote Similarity	NPC477288
0.6197	Remote Similarity	NPC296164
0.6176	Remote Similarity	NPC282616
0.6176	Remote Similarity	NPC275809
0.6176	Remote Similarity	NPC37038
0.6111	Remote Similarity	NPC96580
0.6087	Remote Similarity	NPC106112
0.6087	Remote Similarity	NPC261935
0.6087	Remote Similarity	NPC481360
0.6032	Remote Similarity	NPC142754
0.5921	Remote Similarity	NPC40918
0.5915	Remote Similarity	NPC193750
0.5909	Remote Similarity	NPC3915
0.5833	Remote Similarity	NPC148964
0.5797	Remote Similarity	NPC198664
0.5769	Remote Similarity	NPC476890
0.5769	Remote Similarity	NPC476889
0.5714	Remote Similarity	NPC182797
0.5714	Remote Similarity	NPC121798
0.5714	Remote Similarity	NPC234346
0.5714	Remote Similarity	NPC52169
0.5714	Remote Similarity	NPC488562
0.5694	Remote Similarity	NPC474963
0.5672	Remote Similarity	NPC485430
0.5658	Remote Similarity	NPC481362
0.5632	Remote Similarity	NPC606782
0.5625	Remote Similarity	NPC283849
0.5625	Remote Similarity	NPC28198
0.5625	Remote Similarity	NPC476123
0.561	Remote Similarity	NPC100383
0.56	Remote Similarity	NPC474727
0.5588	Remote Similarity	NPC267517
0.5542	Remote Similarity	NPC43353
0.5538	Remote Similarity	NPC82477
0.55	Remote Similarity	NPC204407
0.5493	Remote Similarity	NPC307282
0.5493	Remote Similarity	NPC64872
0.5493	Remote Similarity	NPC25906
0.5467	Remote Similarity	NPC6255
0.5432	Remote Similarity	NPC606107
0.5417	Remote Similarity	NPC130278
0.5417	Remote Similarity	NPC472149
0.5417	Remote Similarity	NPC609452
0.5405	Remote Similarity	NPC471588
0.5405	Remote Similarity	NPC105189
0.5405	Remote Similarity	NPC481316
0.5405	Remote Similarity	NPC608622
0.5301	Remote Similarity	NPC286347
0.5294	Remote Similarity	NPC294112
0.5294	Remote Similarity	NPC284807
0.5294	Remote Similarity	NPC473538
0.5286	Remote Similarity	NPC251779
0.527	Remote Similarity	NPC474964
0.5217	Remote Similarity	NPC161496
0.5211	Remote Similarity	NPC80784
0.5205	Remote Similarity	NPC271614
0.5205	Remote Similarity	NPC88116
0.52	Remote Similarity	NPC476064
0.52	Remote Similarity	NPC130520
0.52	Remote Similarity	NPC62516
0.5172	Remote Similarity	NPC475472
0.5172	Remote Similarity	NPC475611
0.5143	Remote Similarity	NPC133954
0.5139	Remote Similarity	NPC474806
0.5139	Remote Similarity	NPC133579
0.5135	Remote Similarity	NPC228784
0.5135	Remote Similarity	NPC324341
0.5135	Remote Similarity	NPC601810
0.5132	Remote Similarity	NPC324063
0.5132	Remote Similarity	NPC222047
0.5132	Remote Similarity	NPC488521
0.5114	Remote Similarity	NPC22676
0.5068	Remote Similarity	NPC51700
0.5068	Remote Similarity	NPC88716
0.5068	Remote Similarity	NPC32118
0.5068	Remote Similarity	NPC68160
0.5068	Remote Similarity	NPC606443
0.5067	Remote Similarity	NPC485589
0.5067	Remote Similarity	NPC201657
0.5063	Remote Similarity	NPC188833
0.5057	Remote Similarity	NPC191410
0.5056	Remote Similarity	NPC198621
0.5056	Remote Similarity	NPC216940

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC49818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6614
0.1-0.2	2490
0.2-0.3	36
0.3-0.4	9
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
0.5632	Remote Similarity	NPD8166	Discontinued

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