NPASS Compound

Structure

CID253627 OpenBabel06191716052D 22 24 0 0 1 0 0 0 0 0999 V2000 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2321 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 8 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 19 1 0 0 0 0 12 21 2 0 0 0 0 13 18 1 0 0 0 0 14 15 2 0 0 0 0 14 18 1 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 19 1 1 0 0 0 17 20 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.21
Volume:	335.841
LogP:	4.371
LogD:	4.006
LogS:	-4.69
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.802
Synthetic Accessibility Score:	3.892
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.864
MDCK Permeability:	2.2296297174762003e-05
Pgp-inhibitor:	0.345
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117
Plasma Protein Binding (PPB):	83.97310638427734%
Volume Distribution (VD):	2.579
Pgp-substrate:	10.278738021850586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.065
CYP1A2-substrate:	0.82
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.838
CYP2C9-inhibitor:	0.091
CYP2C9-substrate:	0.598
CYP2D6-inhibitor:	0.864
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.85
CYP3A4-substrate:	0.752

ADMET: Excretion

Clearance (CL):	6.71
Half-life (T1/2):	0.184

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.102
Drug-inuced Liver Injury (DILI):	0.275
AMES Toxicity:	0.181
Rat Oral Acute Toxicity:	0.294
Maximum Recommended Daily Dose:	0.617
Skin Sensitization:	0.941
Carcinogencity:	0.301
Eye Corrosion:	0.019
Eye Irritation:	0.647
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC253627

Natural Product ID:	NPC253627
*Common Name:**	Totaral
IUPAC Name:	(1S,4aS,10aR)-7-hydroxy-1,4a-dimethyl-8-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carbaldehyde
Synonyms:	Totaral
Standard InCHIKey:	QMRLEXVAVRHWSE-DFQSSKMNSA-N
Standard InCHI:	InChI=1S/C20H28O2/c1-13(2)18-14-6-9-17-19(3,12-21)10-5-11-20(17,4)15(14)7-8-16(18)22/h7-8,12-13,17,22H,5-6,9-11H2,1-4H3/t17-,19+,20+/m0/s1
SMILES:	CC(C)c1c2CC[C@H]3[C@](C)(CCC[C@]3(C)c2ccc1O)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478772
PubChem CID:	15694358
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO9389	Swertia bimaculata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/cbdv.200490123]
NPO9389	Swertia bimaculata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)98635-7]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869194]
NPO6506	Cupaniopsis macropetala	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18163587]
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]
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]
NPO9921	Peyronellaea glomerata	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29738260]
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]
NPO1849	Pleiospermium alatum	Species	Rutaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO1849	Pleiospermium alatum	Species	Rutaceae	Eukaryota	n.a.	stem	n.a.	Database[Article]
NPO1849	Pleiospermium alatum	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15989	Rabdosia yuennanensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14112	Uncaria rhynchophylla	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[TM-MC]
NPO15179	Cocculus hirsutus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO930	Psalliota campestris	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO22	Osmitopsis asteriscoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2771	Teucrium ramosissimum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14755	Ornithogalum montanum	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1849	Pleiospermium alatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25110	Neomirandea angularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15989	Rabdosia yuennanensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9389	Swertia bimaculata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6506	Cupaniopsis macropetala	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9921	Peyronellaea glomerata	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4452	Erythrina falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14606	Leucanthemella serotina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14265	Stokesia laevis	Species	Asteraceae	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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	80.52	%	PMID[487478]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	100.85	%	PMID[487478]

☑ 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 NPC253627 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	236
0.1-0.2	1352
0.2-0.3	2700
0.3-0.4	8066
0.4-0.5	10786
0.5-0.6	8797
0.6-0.7	8906
0.7-0.8	1656
0.8-0.85	121
0.85-0.9	60
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9741	High Similarity	NPC11250
0.9496	High Similarity	NPC137750
0.9492	High Similarity	NPC198014
0.9333	High Similarity	NPC87985
0.9328	High Similarity	NPC471187
0.925	High Similarity	NPC181334
0.9237	High Similarity	NPC259703
0.9237	High Similarity	NPC32322
0.916	High Similarity	NPC162935
0.916	High Similarity	NPC249340
0.913	High Similarity	NPC268160
0.9098	High Similarity	NPC71610
0.9083	High Similarity	NPC121168
0.9083	High Similarity	NPC176208
0.9076	High Similarity	NPC241001
0.9068	High Similarity	NPC42657
0.9052	High Similarity	NPC147179
0.9	High Similarity	NPC154696
0.8992	High Similarity	NPC318552
0.8992	High Similarity	NPC190501
0.8974	High Similarity	NPC308828
0.8974	High Similarity	NPC219112
0.8952	High Similarity	NPC3009
0.8947	High Similarity	NPC141782
0.8898	High Similarity	NPC477139
0.8889	High Similarity	NPC35797
0.8889	High Similarity	NPC291001
0.8889	High Similarity	NPC192948
0.8833	High Similarity	NPC478121
0.8824	High Similarity	NPC469609
0.8814	High Similarity	NPC38893
0.8814	High Similarity	NPC477137
0.8814	High Similarity	NPC308311
0.874	High Similarity	NPC471851
0.8739	High Similarity	NPC304510
0.8739	High Similarity	NPC477136
0.8739	High Similarity	NPC172219
0.873	High Similarity	NPC276238
0.872	High Similarity	NPC262936
0.872	High Similarity	NPC30491
0.872	High Similarity	NPC78364
0.872	High Similarity	NPC176130
0.872	High Similarity	NPC69424
0.872	High Similarity	NPC84672
0.8707	High Similarity	NPC260323
0.8707	High Similarity	NPC176279
0.8678	High Similarity	NPC135467
0.8678	High Similarity	NPC260832
0.8667	High Similarity	NPC471671
0.8655	High Similarity	NPC92
0.8655	High Similarity	NPC469663
0.8644	High Similarity	NPC195922
0.8632	High Similarity	NPC250323
0.8621	High Similarity	NPC13482
0.8607	High Similarity	NPC164852
0.8605	High Similarity	NPC78307
0.8605	High Similarity	NPC49742
0.8595	High Similarity	NPC79933
0.8595	High Similarity	NPC473974
0.8595	High Similarity	NPC31296
0.8595	High Similarity	NPC469644
0.8595	High Similarity	NPC258366
0.8594	High Similarity	NPC476847
0.8583	High Similarity	NPC303910
0.8583	High Similarity	NPC16030
0.8571	High Similarity	NPC72667
0.8547	High Similarity	NPC95716
0.8538	High Similarity	NPC202225
0.8527	High Similarity	NPC165612
0.8516	High Similarity	NPC108129
0.85	High Similarity	NPC471668
0.8492	Intermediate Similarity	NPC254492
0.848	Intermediate Similarity	NPC15127
0.848	Intermediate Similarity	NPC199273
0.8475	Intermediate Similarity	NPC46940
0.8475	Intermediate Similarity	NPC228425
0.8473	Intermediate Similarity	NPC103082
0.8468	Intermediate Similarity	NPC471794
0.8462	Intermediate Similarity	NPC476282
0.845	Intermediate Similarity	NPC85342
0.845	Intermediate Similarity	NPC243305
0.8448	Intermediate Similarity	NPC11554
0.8444	Intermediate Similarity	NPC477209
0.8438	Intermediate Similarity	NPC206028
0.8438	Intermediate Similarity	NPC171460
0.8438	Intermediate Similarity	NPC131684
0.8403	Intermediate Similarity	NPC715
0.839	Intermediate Similarity	NPC322753
0.839	Intermediate Similarity	NPC77772
0.8382	Intermediate Similarity	NPC199936
0.8362	Intermediate Similarity	NPC151477
0.8362	Intermediate Similarity	NPC228737
0.8361	Intermediate Similarity	NPC328694
0.8361	Intermediate Similarity	NPC164649
0.8361	Intermediate Similarity	NPC48342
0.8361	Intermediate Similarity	NPC154030
0.8359	Intermediate Similarity	NPC96024
0.8346	Intermediate Similarity	NPC475957
0.8346	Intermediate Similarity	NPC269598
0.8333	Intermediate Similarity	NPC471534
0.8333	Intermediate Similarity	NPC75432
0.832	Intermediate Similarity	NPC478058
0.8319	Intermediate Similarity	NPC286222
0.8308	Intermediate Similarity	NPC41847
0.8306	Intermediate Similarity	NPC21216
0.8306	Intermediate Similarity	NPC328504
0.8305	Intermediate Similarity	NPC132720
0.8296	Intermediate Similarity	NPC476534
0.8293	Intermediate Similarity	NPC93071
0.8293	Intermediate Similarity	NPC126002
0.8284	Intermediate Similarity	NPC477593
0.8268	Intermediate Similarity	NPC137416
0.8264	Intermediate Similarity	NPC469719
0.8258	Intermediate Similarity	NPC194970
0.8235	Intermediate Similarity	NPC471188
0.8235	Intermediate Similarity	NPC266937
0.8235	Intermediate Similarity	NPC470770
0.8222	Intermediate Similarity	NPC76312
0.822	Intermediate Similarity	NPC58865
0.8217	Intermediate Similarity	NPC229894
0.8203	Intermediate Similarity	NPC227741
0.8203	Intermediate Similarity	NPC295202
0.8203	Intermediate Similarity	NPC49647
0.8203	Intermediate Similarity	NPC136342
0.8201	Intermediate Similarity	NPC477208
0.8197	Intermediate Similarity	NPC474358
0.8197	Intermediate Similarity	NPC257540
0.8197	Intermediate Similarity	NPC154511
0.8197	Intermediate Similarity	NPC137496
0.8197	Intermediate Similarity	NPC247858
0.8197	Intermediate Similarity	NPC141001
0.8197	Intermediate Similarity	NPC474387
0.8195	Intermediate Similarity	NPC153088
0.8195	Intermediate Similarity	NPC279463
0.819	Intermediate Similarity	NPC117115
0.8182	Intermediate Similarity	NPC475627
0.8182	Intermediate Similarity	NPC475457
0.8182	Intermediate Similarity	NPC18982
0.8182	Intermediate Similarity	NPC111845
0.8182	Intermediate Similarity	NPC475346
0.8175	Intermediate Similarity	NPC282577
0.8168	Intermediate Similarity	NPC258073
0.8168	Intermediate Similarity	NPC18798
0.8167	Intermediate Similarity	NPC177962
0.8167	Intermediate Similarity	NPC228988
0.8167	Intermediate Similarity	NPC62867
0.816	Intermediate Similarity	NPC216216
0.8154	Intermediate Similarity	NPC474546
0.8154	Intermediate Similarity	NPC117899
0.8145	Intermediate Similarity	NPC151197
0.8145	Intermediate Similarity	NPC182240
0.814	Intermediate Similarity	NPC471530
0.813	Intermediate Similarity	NPC174087
0.8125	Intermediate Similarity	NPC131799
0.812	Intermediate Similarity	NPC293454
0.812	Intermediate Similarity	NPC213122
0.812	Intermediate Similarity	NPC21594
0.812	Intermediate Similarity	NPC271274
0.8116	Intermediate Similarity	NPC477207
0.811	Intermediate Similarity	NPC273683
0.811	Intermediate Similarity	NPC275145
0.8102	Intermediate Similarity	NPC272907
0.8102	Intermediate Similarity	NPC2681
0.8095	Intermediate Similarity	NPC142198
0.8095	Intermediate Similarity	NPC295034
0.8095	Intermediate Similarity	NPC77569
0.8083	Intermediate Similarity	NPC151537
0.808	Intermediate Similarity	NPC133389
0.808	Intermediate Similarity	NPC473136
0.808	Intermediate Similarity	NPC234337
0.808	Intermediate Similarity	NPC183339
0.8077	Intermediate Similarity	NPC48248
0.8077	Intermediate Similarity	NPC193203
0.8074	Intermediate Similarity	NPC277559
0.8074	Intermediate Similarity	NPC49911
0.8074	Intermediate Similarity	NPC477592
0.8067	Intermediate Similarity	NPC314187
0.8062	Intermediate Similarity	NPC325294
0.8062	Intermediate Similarity	NPC321822
0.8062	Intermediate Similarity	NPC100414
0.8062	Intermediate Similarity	NPC43000
0.806	Intermediate Similarity	NPC472804
0.806	Intermediate Similarity	NPC477874
0.806	Intermediate Similarity	NPC173569
0.8051	Intermediate Similarity	NPC320439
0.8047	Intermediate Similarity	NPC173978
0.8047	Intermediate Similarity	NPC474766
0.8047	Intermediate Similarity	NPC10154
0.8047	Intermediate Similarity	NPC234890
0.8047	Intermediate Similarity	NPC74507
0.8047	Intermediate Similarity	NPC265413
0.8045	Intermediate Similarity	NPC138472
0.8031	Intermediate Similarity	NPC152946
0.803	Intermediate Similarity	NPC72669
0.803	Intermediate Similarity	NPC474517
0.803	Intermediate Similarity	NPC93015
0.8029	Intermediate Similarity	NPC471853
0.8029	Intermediate Similarity	NPC3218
0.8015	Intermediate Similarity	NPC99731
0.8015	Intermediate Similarity	NPC206207

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 NPC253627 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	943
0.2-0.3	1227
0.3-0.4	2602
0.4-0.5	2248
0.5-0.6	1318
0.6-0.7	487
0.7-0.8	72
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8992	High Similarity	NPD3019	Approved
0.8833	High Similarity	NPD2932	Approved
0.845	Intermediate Similarity	NPD6663	Approved
0.8425	Intermediate Similarity	NPD5736	Approved
0.8361	Intermediate Similarity	NPD3091	Approved
0.8306	Intermediate Similarity	NPD3026	Approved
0.8306	Intermediate Similarity	NPD3023	Approved
0.8293	Intermediate Similarity	NPD3025	Approved
0.8293	Intermediate Similarity	NPD3024	Approved
0.8095	Intermediate Similarity	NPD3092	Approved
0.7953	Intermediate Similarity	NPD1201	Approved
0.7937	Intermediate Similarity	NPD4059	Approved
0.7937	Intermediate Similarity	NPD3095	Discontinued
0.7899	Intermediate Similarity	NPD2342	Discontinued
0.7869	Intermediate Similarity	NPD7635	Approved
0.7846	Intermediate Similarity	NPD3094	Phase 2
0.7786	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD1283	Approved
0.7759	Intermediate Similarity	NPD3020	Approved
0.7746	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD1651	Approved
0.7714	Intermediate Similarity	NPD7003	Approved
0.7714	Intermediate Similarity	NPD8166	Discontinued
0.771	Intermediate Similarity	NPD1470	Approved
0.7652	Intermediate Similarity	NPD1809	Phase 2
0.7609	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD288	Approved
0.7578	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD5406	Approved
0.7554	Intermediate Similarity	NPD5404	Approved
0.7554	Intermediate Similarity	NPD5405	Approved
0.7554	Intermediate Similarity	NPD5408	Approved
0.7542	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD1281	Approved
0.7519	Intermediate Similarity	NPD4626	Approved
0.75	Intermediate Similarity	NPD844	Approved
0.75	Intermediate Similarity	NPD2859	Approved
0.75	Intermediate Similarity	NPD2860	Approved
0.75	Intermediate Similarity	NPD8032	Phase 2
0.7482	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD3021	Approved
0.748	Intermediate Similarity	NPD3022	Approved
0.7478	Intermediate Similarity	NPD845	Approved
0.7464	Intermediate Similarity	NPD4097	Suspended
0.746	Intermediate Similarity	NPD5951	Approved
0.7445	Intermediate Similarity	NPD4140	Approved
0.7445	Intermediate Similarity	NPD4060	Phase 1
0.7442	Intermediate Similarity	NPD4093	Discontinued
0.7414	Intermediate Similarity	NPD2933	Approved
0.7414	Intermediate Similarity	NPD2934	Approved
0.7388	Intermediate Similarity	NPD4624	Approved
0.7385	Intermediate Similarity	NPD1751	Approved
0.7385	Intermediate Similarity	NPD2286	Discontinued
0.736	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD4750	Phase 3
0.7329	Intermediate Similarity	NPD6273	Approved
0.7319	Intermediate Similarity	NPD3620	Phase 2
0.7319	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD2979	Phase 3
0.731	Intermediate Similarity	NPD7390	Discontinued
0.7308	Intermediate Similarity	NPD5691	Approved
0.7305	Intermediate Similarity	NPD6100	Approved
0.7305	Intermediate Similarity	NPD6099	Approved
0.7293	Intermediate Similarity	NPD5327	Phase 3
0.7279	Intermediate Similarity	NPD2606	Approved
0.7279	Intermediate Similarity	NPD2605	Approved
0.7244	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7743	Approved
0.7234	Intermediate Similarity	NPD7742	Approved
0.7226	Intermediate Similarity	NPD5156	Approved
0.7226	Intermediate Similarity	NPD5155	Approved
0.7206	Intermediate Similarity	NPD3637	Approved
0.7206	Intermediate Similarity	NPD3635	Approved
0.7206	Intermediate Similarity	NPD3636	Approved
0.7188	Intermediate Similarity	NPD2629	Approved
0.7185	Intermediate Similarity	NPD1164	Approved
0.7183	Intermediate Similarity	NPD4477	Approved
0.7183	Intermediate Similarity	NPD2935	Discontinued
0.7183	Intermediate Similarity	NPD4476	Approved
0.7181	Intermediate Similarity	NPD7458	Discontinued
0.7164	Intermediate Similarity	NPD1755	Approved
0.7153	Intermediate Similarity	NPD3595	Approved
0.7153	Intermediate Similarity	NPD3594	Approved
0.7143	Intermediate Similarity	NPD5735	Approved
0.7143	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2195	Approved
0.7132	Intermediate Similarity	NPD2194	Approved
0.7121	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD4589	Approved
0.7121	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6353	Approved
0.708	Intermediate Similarity	NPD4208	Discontinued
0.7077	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2438	Suspended
0.7063	Intermediate Similarity	NPD2531	Phase 2
0.7063	Intermediate Similarity	NPD1792	Phase 2
0.7059	Intermediate Similarity	NPD2797	Approved
0.705	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6798	Discontinued
0.705	Intermediate Similarity	NPD3764	Approved
0.7049	Intermediate Similarity	NPD940	Approved
0.7049	Intermediate Similarity	NPD846	Approved
0.7034	Intermediate Similarity	NPD3638	Discontinued
0.7027	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6355	Discontinued
0.7007	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3300	Phase 2
0.6992	Remote Similarity	NPD1778	Approved
0.6992	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4110	Phase 3
0.6986	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6696	Suspended
0.6978	Remote Similarity	NPD7095	Approved
0.6978	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7008	Discontinued
0.6978	Remote Similarity	NPD4625	Phase 3
0.6977	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2229	Approved
0.6977	Remote Similarity	NPD2228	Approved
0.6977	Remote Similarity	NPD2234	Approved
0.697	Remote Similarity	NPD5303	Approved
0.697	Remote Similarity	NPD5304	Approved
0.6963	Remote Similarity	NPD3972	Approved
0.6957	Remote Similarity	NPD2861	Phase 2
0.6934	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7427	Discontinued
0.6929	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD37	Approved
0.6923	Remote Similarity	NPD497	Approved
0.6918	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5585	Approved
0.6906	Remote Similarity	NPD4908	Phase 1
0.6897	Remote Similarity	NPD4725	Approved
0.6897	Remote Similarity	NPD2346	Discontinued
0.6897	Remote Similarity	NPD4721	Approved
0.6897	Remote Similarity	NPD4726	Approved
0.6884	Remote Similarity	NPD2798	Approved
0.6875	Remote Similarity	NPD2799	Discontinued
0.6871	Remote Similarity	NPD3400	Discontinued
0.687	Remote Similarity	NPD255	Approved
0.687	Remote Similarity	NPD256	Approved
0.6861	Remote Similarity	NPD1876	Approved
0.6853	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD498	Approved
0.6846	Remote Similarity	NPD495	Approved
0.6846	Remote Similarity	NPD496	Approved
0.6846	Remote Similarity	NPD7041	Phase 2
0.6846	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1608	Approved
0.6835	Remote Similarity	NPD6959	Discontinued
0.6829	Remote Similarity	NPD1242	Phase 1
0.6825	Remote Similarity	NPD1444	Approved
0.6825	Remote Similarity	NPD1445	Approved
0.6818	Remote Similarity	NPD7340	Approved
0.6815	Remote Similarity	NPD6234	Discontinued
0.6809	Remote Similarity	NPD3268	Approved
0.68	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7028	Phase 2
0.6795	Remote Similarity	NPD4967	Phase 2
0.6795	Remote Similarity	NPD4965	Approved
0.6795	Remote Similarity	NPD4966	Approved
0.6792	Remote Similarity	NPD6232	Discontinued
0.6786	Remote Similarity	NPD4207	Discontinued
0.6783	Remote Similarity	NPD111	Approved
0.6781	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7819	Suspended
0.677	Remote Similarity	NPD7473	Discontinued
0.6765	Remote Similarity	NPD1610	Phase 2
0.6763	Remote Similarity	NPD6584	Phase 3
0.6757	Remote Similarity	NPD4628	Phase 3
0.6742	Remote Similarity	NPD3317	Approved
0.6742	Remote Similarity	NPD4198	Discontinued
0.6742	Remote Similarity	NPD6671	Approved
0.6741	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7037	Approved
0.6735	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3226	Approved
0.6731	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.673	Remote Similarity	NPD8127	Discontinued
0.6718	Remote Similarity	NPD1398	Phase 1
0.6718	Remote Similarity	NPD5283	Phase 1
0.6716	Remote Similarity	NPD7330	Discontinued
0.6716	Remote Similarity	NPD9545	Approved
0.6716	Remote Similarity	NPD1894	Discontinued
0.6715	Remote Similarity	NPD2232	Approved
0.6715	Remote Similarity	NPD2230	Approved
0.6715	Remote Similarity	NPD2233	Approved
0.6714	Remote Similarity	NPD9494	Approved
0.6713	Remote Similarity	NPD943	Approved
0.6713	Remote Similarity	NPD826	Approved
0.6713	Remote Similarity	NPD825	Approved
0.6694	Remote Similarity	NPD688	Clinical (unspecified phase)

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