NPASS Compound

Structure

CID24556 OpenBabel06191715352D 30 35 0 0 1 0 0 0 0 0999 V2000 3.5827 -0.7834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3104 -2.5222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4137 -3.7052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8950 -2.2523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1181 -1.7501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2783 -1.2659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0760 -1.6533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1192 -4.6572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6010 -3.2053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2798 -4.1735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7613 -2.7211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0714 -1.6533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9581 -3.2032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7596 0.1856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0760 0.0865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5782 -0.7834 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.5668 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1186 -2.7195 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9584 -4.1720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4391 -1.7511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4397 -2.7204 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5994 -1.2669 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9209 -0.2992 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9209 -1.2676 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2795 -3.2046 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7607 -1.7518 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5692 -0.7834 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8246 -4.6716 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0714 0.0865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 17 1 0 0 0 0 5 6 1 0 0 0 0 5 18 1 0 0 0 0 7 12 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 21 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 29 1 0 0 0 0 16 1 1 6 0 0 0 17 24 1 0 0 0 0 17 27 1 1 0 0 0 18 25 1 6 0 0 0 19 28 2 0 0 0 0 20 6 1 1 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 25 1 6 0 0 0 22 26 1 6 0 0 0 23 14 1 6 0 0 0 23 24 1 0 0 0 0 23 30 1 0 0 0 0 24 26 1 6 0 0 0 25 3 1 6 0 0 0 26 4 1 6 0 0 0 27 12 1 6 0 0 0 27 29 1 0 0 0 0 27 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.31
Volume:	447.944
LogP:	5.958
LogD:	4.981
LogS:	-4.939
# Rotatable Bonds:	0
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.487
Synthetic Accessibility Score:	5.211
Fsp3:	0.963
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.872
MDCK Permeability:	1.5091151908563916e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.736
Plasma Protein Binding (PPB):	90.75836944580078%
Volume Distribution (VD):	1.441
Pgp-substrate:	2.0452208518981934%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.533
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.839
CYP2C9-inhibitor:	0.267
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.517
CYP3A4-inhibitor:	0.643
CYP3A4-substrate:	0.413

ADMET: Excretion

Clearance (CL):	20.019
Half-life (T1/2):	0.337

ADMET: Toxicity

hERG Blockers:	0.997
Human Hepatotoxicity (H-HT):	0.401
Drug-inuced Liver Injury (DILI):	0.885
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.263
Maximum Recommended Daily Dose:	0.79
Skin Sensitization:	0.961
Carcinogencity:	0.559
Eye Corrosion:	0.548
Eye Irritation:	0.385
Respiratory Toxicity:	0.982

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC24556

Natural Product ID:	NPC24556
*Common Name:**	CIBAPVLFORANSS-AIEOQHCFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CIBAPVLFORANSS-AIEOQHCFSA-N
Standard InCHI:	InChI=1S/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-18,20-24H,5-15H2,1-4H3/t16-,17+,18+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1
SMILES:	C[C@@H]1CC[C@@]2(OC1)O[C@@H]1[C@H]([C@@H]2C)[C@@]2([C@@H](C1)[C@@H]1CC[C@@H]3[C@]([C@H]1CC2)(C)CCC(=O)C3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1770684
PubChem CID:	101692
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11599360]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381697]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO14899	Agave sisalana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7830	Agave angustifolia	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23541	Smilax sieboldii	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8976	Agave americana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12948	Solanum dulcamara	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7928	Agave east-one	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8976.1	Agave americana var. marginata	Varieties	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO21651	Cheilocostus speciosus	Species	Costaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8976	Agave americana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8976.1	Agave americana var. marginata	Varieties	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12948	Solanum dulcamara	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7830	Agave angustifolia	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7928	Agave east-one	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23541	Smilax sieboldii	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14899	Agave sisalana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8976	Agave americana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23541	Smilax sieboldii	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14899	Agave sisalana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7830	Agave angustifolia	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12948	Solanum dulcamara	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23541	Smilax sieboldii	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14899	Agave sisalana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12948	Solanum dulcamara	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21651	Cheilocostus speciosus	Species	Costaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8976	Agave americana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7830	Agave angustifolia	Species	Asparagaceae	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	NP ID	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
Others	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	Inhibition	<	25.0	%	PMID[464096]
NPT554	Organism	Candida glabrata	Candida glabrata	Inhibition	<	25.0	%	PMID[464096]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	<	25.0	%	PMID[464096]
NPT20	Organism	Candida albicans	Candida albicans	Inhibition	<	25.0	%	PMID[464096]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC24556 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	448
0.1-0.2	4622
0.2-0.3	14840
0.3-0.4	9293
0.4-0.5	5679
0.5-0.6	5240
0.6-0.7	2113
0.7-0.8	440
0.8-0.85	19
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8837	High Similarity	NPC161035
0.8636	High Similarity	NPC305808
0.8293	Intermediate Similarity	NPC257296
0.8293	Intermediate Similarity	NPC7479
0.8293	Intermediate Similarity	NPC248944
0.8242	Intermediate Similarity	NPC187159
0.8193	Intermediate Similarity	NPC472230
0.8193	Intermediate Similarity	NPC472229
0.8172	Intermediate Similarity	NPC178853
0.8132	Intermediate Similarity	NPC476728
0.8118	Intermediate Similarity	NPC101138
0.8118	Intermediate Similarity	NPC51135
0.8118	Intermediate Similarity	NPC82492
0.8118	Intermediate Similarity	NPC25802
0.8095	Intermediate Similarity	NPC296734
0.8022	Intermediate Similarity	NPC215570
0.7952	Intermediate Similarity	NPC245029
0.7952	Intermediate Similarity	NPC31302
0.7907	Intermediate Similarity	NPC227260
0.7872	Intermediate Similarity	NPC20028
0.7872	Intermediate Similarity	NPC41843
0.7865	Intermediate Similarity	NPC472234
0.7865	Intermediate Similarity	NPC472233
0.7857	Intermediate Similarity	NPC1882
0.7835	Intermediate Similarity	NPC215408
0.7816	Intermediate Similarity	NPC273290
0.7816	Intermediate Similarity	NPC232044
0.7789	Intermediate Similarity	NPC477172
0.7778	Intermediate Similarity	NPC77756
0.775	Intermediate Similarity	NPC197701
0.7727	Intermediate Similarity	NPC474448
0.7708	Intermediate Similarity	NPC80191
0.7708	Intermediate Similarity	NPC310031
0.7677	Intermediate Similarity	NPC202898
0.7677	Intermediate Similarity	NPC92890
0.7677	Intermediate Similarity	NPC475319
0.7674	Intermediate Similarity	NPC470611
0.7654	Intermediate Similarity	NPC474123
0.7654	Intermediate Similarity	NPC310766
0.7609	Intermediate Similarity	NPC472231
0.7609	Intermediate Similarity	NPC472232
0.76	Intermediate Similarity	NPC473817
0.76	Intermediate Similarity	NPC273002
0.76	Intermediate Similarity	NPC220836
0.76	Intermediate Similarity	NPC94086
0.76	Intermediate Similarity	NPC92297
0.76	Intermediate Similarity	NPC233433
0.7586	Intermediate Similarity	NPC268578
0.7586	Intermediate Similarity	NPC292458
0.7586	Intermediate Similarity	NPC217559
0.7558	Intermediate Similarity	NPC469745
0.7526	Intermediate Similarity	NPC213528
0.7526	Intermediate Similarity	NPC244969
0.75	Intermediate Similarity	NPC474404
0.75	Intermediate Similarity	NPC473336
0.75	Intermediate Similarity	NPC321732
0.75	Intermediate Similarity	NPC324607
0.75	Intermediate Similarity	NPC471044
0.75	Intermediate Similarity	NPC52756
0.7474	Intermediate Similarity	NPC472273
0.7474	Intermediate Similarity	NPC471241
0.7473	Intermediate Similarity	NPC200580
0.747	Intermediate Similarity	NPC72444
0.7451	Intermediate Similarity	NPC473062
0.7449	Intermediate Similarity	NPC107385
0.7442	Intermediate Similarity	NPC470609
0.7442	Intermediate Similarity	NPC472853
0.7419	Intermediate Similarity	NPC228700
0.7419	Intermediate Similarity	NPC476189
0.7419	Intermediate Similarity	NPC472238
0.7419	Intermediate Similarity	NPC472237
0.7391	Intermediate Similarity	NPC473542
0.7386	Intermediate Similarity	NPC472744
0.7381	Intermediate Similarity	NPC471046
0.7374	Intermediate Similarity	NPC470167
0.7374	Intermediate Similarity	NPC100078
0.7368	Intermediate Similarity	NPC193785
0.7368	Intermediate Similarity	NPC116683
0.7368	Intermediate Similarity	NPC156377
0.7363	Intermediate Similarity	NPC33398
0.7356	Intermediate Similarity	NPC58631
0.7356	Intermediate Similarity	NPC77311
0.7353	Intermediate Similarity	NPC106760
0.7349	Intermediate Similarity	NPC472854
0.7347	Intermediate Similarity	NPC470172
0.734	Intermediate Similarity	NPC206878
0.734	Intermediate Similarity	NPC470423
0.734	Intermediate Similarity	NPC470424
0.734	Intermediate Similarity	NPC477495
0.7333	Intermediate Similarity	NPC80700
0.7333	Intermediate Similarity	NPC472745
0.7327	Intermediate Similarity	NPC472079
0.7327	Intermediate Similarity	NPC61411
0.7326	Intermediate Similarity	NPC80891
0.7326	Intermediate Similarity	NPC201276
0.7326	Intermediate Similarity	NPC477287
0.7326	Intermediate Similarity	NPC476176
0.7317	Intermediate Similarity	NPC156277
0.7317	Intermediate Similarity	NPC58057
0.7317	Intermediate Similarity	NPC151018
0.7317	Intermediate Similarity	NPC320549
0.7317	Intermediate Similarity	NPC469940
0.7312	Intermediate Similarity	NPC149966
0.7312	Intermediate Similarity	NPC5632
0.7312	Intermediate Similarity	NPC475878
0.7312	Intermediate Similarity	NPC59006
0.7303	Intermediate Similarity	NPC474996
0.7303	Intermediate Similarity	NPC473299
0.73	Intermediate Similarity	NPC306776
0.73	Intermediate Similarity	NPC166079
0.7294	Intermediate Similarity	NPC477918
0.7284	Intermediate Similarity	NPC178541
0.7283	Intermediate Similarity	NPC61688
0.7283	Intermediate Similarity	NPC228059
0.7282	Intermediate Similarity	NPC470311
0.7273	Intermediate Similarity	NPC242771
0.7273	Intermediate Similarity	NPC102156
0.7273	Intermediate Similarity	NPC13494
0.7273	Intermediate Similarity	NPC148740
0.7273	Intermediate Similarity	NPC221421
0.7273	Intermediate Similarity	NPC34562
0.7273	Intermediate Similarity	NPC473406
0.7273	Intermediate Similarity	NPC100366
0.7273	Intermediate Similarity	NPC289486
0.7273	Intermediate Similarity	NPC311642
0.7273	Intermediate Similarity	NPC61107
0.7273	Intermediate Similarity	NPC164289
0.7262	Intermediate Similarity	NPC195155
0.7262	Intermediate Similarity	NPC174964
0.7262	Intermediate Similarity	NPC97534
0.7253	Intermediate Similarity	NPC210658
0.7253	Intermediate Similarity	NPC161928
0.7241	Intermediate Similarity	NPC261616
0.7241	Intermediate Similarity	NPC125366
0.7241	Intermediate Similarity	NPC475456
0.7234	Intermediate Similarity	NPC211845
0.7234	Intermediate Similarity	NPC475700
0.7234	Intermediate Similarity	NPC477547
0.7234	Intermediate Similarity	NPC167644
0.7234	Intermediate Similarity	NPC256104
0.7234	Intermediate Similarity	NPC149400
0.7234	Intermediate Similarity	NPC35164
0.7234	Intermediate Similarity	NPC234352
0.7234	Intermediate Similarity	NPC48339
0.7234	Intermediate Similarity	NPC144790
0.7234	Intermediate Similarity	NPC297348
0.7234	Intermediate Similarity	NPC325828
0.7234	Intermediate Similarity	NPC122083
0.7234	Intermediate Similarity	NPC88962
0.7234	Intermediate Similarity	NPC141769
0.7234	Intermediate Similarity	NPC177834
0.7234	Intermediate Similarity	NPC249204
0.7234	Intermediate Similarity	NPC477451
0.7234	Intermediate Similarity	NPC311246
0.7234	Intermediate Similarity	NPC182740
0.7234	Intermediate Similarity	NPC250393
0.7229	Intermediate Similarity	NPC232112
0.7209	Intermediate Similarity	NPC476732
0.7209	Intermediate Similarity	NPC80089
0.7209	Intermediate Similarity	NPC34046
0.7209	Intermediate Similarity	NPC471045
0.7209	Intermediate Similarity	NPC171426
0.7209	Intermediate Similarity	NPC224802
0.7209	Intermediate Similarity	NPC324700
0.7209	Intermediate Similarity	NPC199965
0.7204	Intermediate Similarity	NPC18536
0.7204	Intermediate Similarity	NPC50443
0.7204	Intermediate Similarity	NPC219495
0.72	Intermediate Similarity	NPC88469
0.7195	Intermediate Similarity	NPC108131
0.7195	Intermediate Similarity	NPC477929
0.7184	Intermediate Similarity	NPC163314
0.7176	Intermediate Similarity	NPC475742
0.7176	Intermediate Similarity	NPC5767
0.7174	Intermediate Similarity	NPC221993
0.7174	Intermediate Similarity	NPC28227
0.7174	Intermediate Similarity	NPC128475
0.7174	Intermediate Similarity	NPC281004
0.7172	Intermediate Similarity	NPC94919
0.717	Intermediate Similarity	NPC475490
0.716	Intermediate Similarity	NPC473225
0.7159	Intermediate Similarity	NPC474870
0.7159	Intermediate Similarity	NPC271572
0.7158	Intermediate Similarity	NPC175
0.7158	Intermediate Similarity	NPC222731
0.7158	Intermediate Similarity	NPC473851
0.7158	Intermediate Similarity	NPC477224
0.7158	Intermediate Similarity	NPC217205
0.7158	Intermediate Similarity	NPC3538
0.7158	Intermediate Similarity	NPC41649
0.7158	Intermediate Similarity	NPC312678
0.7158	Intermediate Similarity	NPC473774
0.7158	Intermediate Similarity	NPC113500
0.7158	Intermediate Similarity	NPC174024
0.7158	Intermediate Similarity	NPC45959
0.7158	Intermediate Similarity	NPC24960
0.7158	Intermediate Similarity	NPC264101
0.7158	Intermediate Similarity	NPC179859
0.7158	Intermediate Similarity	NPC471464
0.7158	Intermediate Similarity	NPC291203

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC24556 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	464
0.1-0.2	4319
0.2-0.3	3123
0.3-0.4	698
0.4-0.5	223
0.5-0.6	245
0.6-0.7	60
0.7-0.8	16
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8293	Intermediate Similarity	NPD6928	Phase 2
0.8205	Intermediate Similarity	NPD5777	Approved
0.7917	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4244	Approved
0.7625	Intermediate Similarity	NPD4245	Approved
0.75	Intermediate Similarity	NPD3698	Phase 2
0.747	Intermediate Similarity	NPD3702	Approved
0.7317	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD8171	Discontinued
0.7209	Intermediate Similarity	NPD6697	Approved
0.7209	Intermediate Similarity	NPD6118	Approved
0.7209	Intermediate Similarity	NPD6115	Approved
0.7209	Intermediate Similarity	NPD6114	Approved
0.7195	Intermediate Similarity	NPD4789	Approved
0.7143	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6116	Phase 1
0.7083	Intermediate Similarity	NPD7991	Discontinued
0.7073	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6412	Phase 2
0.7059	Intermediate Similarity	NPD3703	Phase 2
0.7	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6117	Approved
0.6951	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5360	Phase 3
0.6914	Remote Similarity	NPD4224	Phase 2
0.6905	Remote Similarity	NPD6081	Approved
0.6809	Remote Similarity	NPD6903	Approved
0.6774	Remote Similarity	NPD7146	Approved
0.6774	Remote Similarity	NPD5330	Approved
0.6774	Remote Similarity	NPD6684	Approved
0.6774	Remote Similarity	NPD7521	Approved
0.6774	Remote Similarity	NPD7334	Approved
0.6774	Remote Similarity	NPD6409	Approved
0.6635	Remote Similarity	NPD6008	Approved
0.663	Remote Similarity	NPD4788	Approved
0.6629	Remote Similarity	NPD4238	Approved
0.6629	Remote Similarity	NPD4802	Phase 2
0.6598	Remote Similarity	NPD8035	Phase 2
0.6598	Remote Similarity	NPD8034	Phase 2
0.6514	Remote Similarity	NPD8133	Approved
0.6512	Remote Similarity	NPD4758	Discontinued
0.6489	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6059	Approved
0.646	Remote Similarity	NPD6054	Approved
0.6444	Remote Similarity	NPD3671	Phase 1
0.6421	Remote Similarity	NPD6098	Approved
0.6413	Remote Similarity	NPD1779	Approved
0.6413	Remote Similarity	NPD1780	Approved
0.64	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6940	Discontinued
0.6364	Remote Similarity	NPD6399	Phase 3
0.6356	Remote Similarity	NPD7736	Approved
0.6348	Remote Similarity	NPD6370	Approved
0.6325	Remote Similarity	NPD7507	Approved
0.6289	Remote Similarity	NPD6672	Approved
0.6289	Remote Similarity	NPD5737	Approved
0.6264	Remote Similarity	NPD5364	Discontinued
0.6261	Remote Similarity	NPD6016	Approved
0.6261	Remote Similarity	NPD6015	Approved
0.6239	Remote Similarity	NPD7492	Approved
0.6224	Remote Similarity	NPD6904	Approved
0.6224	Remote Similarity	NPD6673	Approved
0.6224	Remote Similarity	NPD6080	Approved
0.6211	Remote Similarity	NPD4786	Approved
0.6211	Remote Similarity	NPD3666	Approved
0.6211	Remote Similarity	NPD3665	Phase 1
0.6211	Remote Similarity	NPD3133	Approved
0.6207	Remote Similarity	NPD4787	Phase 1
0.6207	Remote Similarity	NPD5988	Approved
0.6186	Remote Similarity	NPD6616	Approved
0.6167	Remote Similarity	NPD7319	Approved
0.6162	Remote Similarity	NPD5207	Approved
0.6154	Remote Similarity	NPD6067	Discontinued
0.6147	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD6001	Approved
0.6134	Remote Similarity	NPD8293	Discontinued
0.6134	Remote Similarity	NPD7078	Approved
0.6126	Remote Similarity	NPD6882	Approved
0.6122	Remote Similarity	NPD5208	Approved
0.6117	Remote Similarity	NPD6083	Phase 2
0.6117	Remote Similarity	NPD6084	Phase 2
0.6095	Remote Similarity	NPD1700	Approved
0.6083	Remote Similarity	NPD6033	Approved
0.6058	Remote Similarity	NPD7638	Approved
0.6055	Remote Similarity	NPD7320	Approved
0.6053	Remote Similarity	NPD6009	Approved
0.604	Remote Similarity	NPD4202	Approved
0.6023	Remote Similarity	NPD2254	Approved
0.6023	Remote Similarity	NPD2686	Approved
0.6023	Remote Similarity	NPD2687	Approved
0.6019	Remote Similarity	NPD5739	Approved
0.6019	Remote Similarity	NPD6675	Approved
0.6019	Remote Similarity	NPD7128	Approved
0.6019	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD7327	Approved
0.6	Remote Similarity	NPD4221	Approved
0.6	Remote Similarity	NPD3667	Approved
0.6	Remote Similarity	NPD7639	Approved
0.6	Remote Similarity	NPD7328	Approved
0.6	Remote Similarity	NPD4223	Phase 3
0.598	Remote Similarity	NPD7900	Approved
0.598	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD5329	Approved
0.5976	Remote Similarity	NPD3198	Approved
0.5948	Remote Similarity	NPD7516	Approved
0.5941	Remote Similarity	NPD6050	Approved
0.5941	Remote Similarity	NPD5693	Phase 1
0.5938	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD3669	Approved
0.5922	Remote Similarity	NPD5695	Phase 3
0.5909	Remote Similarity	NPD6899	Approved
0.5909	Remote Similarity	NPD6881	Approved
0.5909	Remote Similarity	NPD6686	Approved
0.5909	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD5696	Approved
0.59	Remote Similarity	NPD4753	Phase 2
0.59	Remote Similarity	NPD5328	Approved
0.5897	Remote Similarity	NPD8294	Approved
0.5897	Remote Similarity	NPD8377	Approved
0.5895	Remote Similarity	NPD4139	Approved
0.5895	Remote Similarity	NPD4692	Approved
0.5888	Remote Similarity	NPD7632	Discontinued
0.5876	Remote Similarity	NPD4197	Approved
0.5876	Remote Similarity	NPD3668	Phase 3
0.5872	Remote Similarity	NPD6920	Discontinued
0.5856	Remote Similarity	NPD6373	Approved
0.5856	Remote Similarity	NPD6372	Approved
0.5854	Remote Similarity	NPD5956	Approved
0.5849	Remote Similarity	NPD8418	Phase 2
0.5847	Remote Similarity	NPD8335	Approved
0.5847	Remote Similarity	NPD8378	Approved
0.5847	Remote Similarity	NPD8033	Approved
0.5847	Remote Similarity	NPD8380	Approved
0.5847	Remote Similarity	NPD8379	Approved
0.5847	Remote Similarity	NPD8296	Approved
0.5842	Remote Similarity	NPD5692	Phase 3
0.5833	Remote Similarity	NPD6052	Approved
0.5825	Remote Similarity	NPD7748	Approved
0.5818	Remote Similarity	NPD5697	Approved
0.5818	Remote Similarity	NPD5701	Approved
0.581	Remote Similarity	NPD4755	Approved
0.581	Remote Similarity	NPD7902	Approved
0.5804	Remote Similarity	NPD7102	Approved
0.5804	Remote Similarity	NPD7290	Approved
0.5804	Remote Similarity	NPD6883	Approved
0.5789	Remote Similarity	NPD4632	Approved
0.5784	Remote Similarity	NPD5694	Approved
0.5784	Remote Similarity	NPD6079	Approved
0.578	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.578	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD6011	Approved
0.5766	Remote Similarity	NPD6415	Discontinued
0.5758	Remote Similarity	NPD4693	Phase 3
0.5758	Remote Similarity	NPD4688	Approved
0.5758	Remote Similarity	NPD8308	Discontinued
0.5758	Remote Similarity	NPD5205	Approved
0.5758	Remote Similarity	NPD4690	Approved
0.5758	Remote Similarity	NPD4689	Approved
0.5758	Remote Similarity	NPD4138	Approved
0.5758	Remote Similarity	NPD3618	Phase 1
0.5752	Remote Similarity	NPD8130	Phase 1
0.5752	Remote Similarity	NPD6617	Approved
0.5752	Remote Similarity	NPD6650	Approved
0.5752	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6869	Approved
0.5752	Remote Similarity	NPD6649	Approved
0.5752	Remote Similarity	NPD6847	Approved
0.5745	Remote Similarity	NPD3617	Approved
0.5743	Remote Similarity	NPD6051	Approved
0.5714	Remote Similarity	NPD6012	Approved
0.5714	Remote Similarity	NPD6014	Approved
0.5714	Remote Similarity	NPD6013	Approved
0.5702	Remote Similarity	NPD8297	Approved
0.5701	Remote Similarity	NPD5285	Approved
0.5701	Remote Similarity	NPD5286	Approved
0.5701	Remote Similarity	NPD4700	Approved
0.5701	Remote Similarity	NPD4696	Approved
0.5652	Remote Similarity	NPD1810	Approved
0.5652	Remote Similarity	NPD6858	Approved
0.5652	Remote Similarity	NPD7094	Approved
0.5652	Remote Similarity	NPD1811	Approved
0.5648	Remote Similarity	NPD5223	Approved
0.5631	Remote Similarity	NPD5281	Approved
0.5631	Remote Similarity	NPD7515	Phase 2
0.5631	Remote Similarity	NPD5284	Approved
0.563	Remote Similarity	NPD6319	Approved
0.5625	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD8174	Phase 2
0.562	Remote Similarity	NPD8328	Phase 3
0.562	Remote Similarity	NPD7604	Phase 2
0.5619	Remote Similarity	NPD5654	Approved
0.5619	Remote Similarity	NPD5210	Approved
0.5619	Remote Similarity	NPD4629	Approved
0.5618	Remote Similarity	NPD229	Approved
0.56	Remote Similarity	NPD5690	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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