NPASS Compound

Structure

NPC148977 OpenBabel07101719242D 23 26 0 0 1 0 0 0 0 0999 V2000 -2.3997 -1.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3998 -1.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 1.0185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 0.0373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5050 -0.6827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8653 0.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6397 -1.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7148 1.0829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0423 2.3790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2579 -0.7014 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6182 0.3693 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2172 1.6034 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0108 -0.7200 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8868 -1.0520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2471 0.0187 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0411 2.3294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5686 2.5396 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8477 -1.2329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 8 2 0 0 0 0 7 19 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 19 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 6 0 0 0 14 18 1 6 0 0 0 14 20 1 0 0 0 0 15 19 1 1 0 0 0 15 22 1 0 0 0 0 16 20 1 1 0 0 0 16 23 1 0 0 0 0 18 3 1 6 0 0 0 19 12 1 6 0 0 0 20 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	343.985
LogP:	2.496
LogD:	2.785
LogS:	-3.579
# Rotatable Bonds:	1
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.651
Synthetic Accessibility Score:	6.153
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.771
MDCK Permeability:	2.7647758543025702e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.041
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.049
30% Bioavailability (F30%):	0.176

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.887
Plasma Protein Binding (PPB):	78.02812957763672%
Volume Distribution (VD):	1.285
Pgp-substrate:	32.10191345214844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.163
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.77
CYP2C9-inhibitor:	0.056
CYP2C9-substrate:	0.166
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.324
CYP3A4-inhibitor:	0.782
CYP3A4-substrate:	0.189

ADMET: Excretion

Clearance (CL):	2.745
Half-life (T1/2):	0.831

ADMET: Toxicity

hERG Blockers:	0.14
Human Hepatotoxicity (H-HT):	0.218
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.987
Maximum Recommended Daily Dose:	0.993
Skin Sensitization:	0.929
Carcinogencity:	0.198
Eye Corrosion:	0.64
Eye Irritation:	0.865
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC148977

Natural Product ID:	NPC148977
*Common Name:**	Conchitriol
IUPAC Name:	n.a.
Synonyms:	Conchitriol
Standard InCHIKey:	AQCWXXFWDZMZFD-XDKCKUNGSA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-17(2)5-4-6-18(3)13(17)9-16(23)20-8-7-19(11-20,12-21)15(22)10-14(18)20/h7-8,13-16,21-23H,4-6,9-12H2,1-3H3/t13-,14+,15-,16+,18-,19+,20+/m1/s1
SMILES:	OC[C@]12C=C[C@@]3(C1)[C@@H](O)C[C@H]1[C@@]([C@@H]3C[C@H]2O)(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2180483
PubChem CID:	71462730
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
NPO22074	Sideritis sp.	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23046382]
NPO12892	Sideritis spp.	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23675610]
NPO12892	Sideritis spp.	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22074	Sideritis sp.	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	38

Activity Type	# Activity
Cell Line	32
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	17.8	pmol/hr	PMID[547750]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	15.9	pmol/hr	PMID[547750]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	52.6	nmol/min	PMID[547750]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	59.5	nmol/min	PMID[547750]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	19.4	nmol/min	PMID[547750]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	17.6	nmol/min	PMID[547750]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	10.2	nmol/min	PMID[547750]
NPT933	Cell Line	U373 MG	Homo sapiens	Ratio	=	2.3	n.a.	PMID[547750]
NPT933	Cell Line	U373 MG	Homo sapiens	Ratio	=	2.0	n.a.	PMID[547750]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	8.6	nmol	PMID[547750]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	8.9	nmol	PMID[547750]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	19.8	nmol	PMID[547750]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	18.0	nmol	PMID[547750]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	0.87	nmol	PMID[547750]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	0.91	nmol	PMID[547750]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	8.2	nmol/min	PMID[547750]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	18.8	IU	PMID[547750]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	15.0	IU	PMID[547750]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	17.4	IU	PMID[547750]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	1.45	nM	PMID[547751]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	1.48	nM	PMID[547751]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	1.3	nM	PMID[547751]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	1.4	nM	PMID[547751]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	1.05	nM	PMID[547751]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	1.08	nM	PMID[547751]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	430.9	nM	PMID[547751]
NPT933	Cell Line	U373 MG	Homo sapiens	Activity	=	479.6	nM	PMID[547751]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	192.6	nM	PMID[547751]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	188.8	nM	PMID[547751]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	60.6	nM	PMID[547751]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	53.5	nM	PMID[547751]
NPT27	Others	Unspecified		Activity	<	10.0	%	PMID[547750]
NPT27	Others	Unspecified		Activity	=	90.0	%	PMID[547750]
NPT27	Others	Unspecified		Activity	=	0.97	nM	PMID[547751]
NPT27	Others	Unspecified		Activity	=	0.99	nM	PMID[547751]
NPT27	Others	Unspecified		Activity	=	98.0	nM	PMID[547751]
NPT27	Others	Unspecified		Activity	=	93.2	nM	PMID[547751]

☑ 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 NPC148977 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	184
0.1-0.2	1602
0.2-0.3	6082
0.3-0.4	16162
0.4-0.5	8137
0.5-0.6	5540
0.6-0.7	3800
0.7-0.8	1041
0.8-0.85	130
0.85-0.9	15
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC472463
0.9067	High Similarity	NPC471798
0.8987	High Similarity	NPC474493
0.8974	High Similarity	NPC248886
0.8947	High Similarity	NPC11908
0.875	High Similarity	NPC127606
0.875	High Similarity	NPC475798
0.8667	High Similarity	NPC243342
0.8667	High Similarity	NPC477138
0.8667	High Similarity	NPC91858
0.8667	High Similarity	NPC471797
0.863	High Similarity	NPC210323
0.8625	High Similarity	NPC113978
0.8625	High Similarity	NPC141941
0.8625	High Similarity	NPC477818
0.8625	High Similarity	NPC193870
0.8608	High Similarity	NPC476646
0.8608	High Similarity	NPC470383
0.8608	High Similarity	NPC242350
0.859	High Similarity	NPC53744
0.8554	High Similarity	NPC475664
0.8553	High Similarity	NPC291503
0.8553	High Similarity	NPC103822
0.8537	High Similarity	NPC6605
0.8533	High Similarity	NPC471799
0.8533	High Similarity	NPC182717
0.8519	High Similarity	NPC209802
0.8493	Intermediate Similarity	NPC2648
0.8481	Intermediate Similarity	NPC96362
0.8481	Intermediate Similarity	NPC287749
0.8462	Intermediate Similarity	NPC312328
0.8462	Intermediate Similarity	NPC99168
0.8462	Intermediate Similarity	NPC6978
0.8462	Intermediate Similarity	NPC138621
0.8462	Intermediate Similarity	NPC253807
0.8462	Intermediate Similarity	NPC87604
0.8462	Intermediate Similarity	NPC230295
0.8462	Intermediate Similarity	NPC470396
0.8462	Intermediate Similarity	NPC167037
0.8462	Intermediate Similarity	NPC196753
0.8462	Intermediate Similarity	NPC98386
0.8462	Intermediate Similarity	NPC474989
0.8462	Intermediate Similarity	NPC22955
0.8462	Intermediate Similarity	NPC244385
0.8462	Intermediate Similarity	NPC158662
0.8462	Intermediate Similarity	NPC285761
0.8442	Intermediate Similarity	NPC106432
0.8442	Intermediate Similarity	NPC237460
0.8434	Intermediate Similarity	NPC474657
0.8434	Intermediate Similarity	NPC186145
0.8421	Intermediate Similarity	NPC472503
0.8421	Intermediate Similarity	NPC308440
0.8421	Intermediate Similarity	NPC100334
0.8415	Intermediate Similarity	NPC470360
0.84	Intermediate Similarity	NPC110799
0.84	Intermediate Similarity	NPC242001
0.84	Intermediate Similarity	NPC167706
0.8395	Intermediate Similarity	NPC82538
0.8395	Intermediate Similarity	NPC110778
0.8395	Intermediate Similarity	NPC237795
0.8375	Intermediate Similarity	NPC249423
0.8354	Intermediate Similarity	NPC80530
0.8354	Intermediate Similarity	NPC291379
0.8354	Intermediate Similarity	NPC273410
0.8353	Intermediate Similarity	NPC475751
0.8353	Intermediate Similarity	NPC473956
0.8333	Intermediate Similarity	NPC157996
0.8333	Intermediate Similarity	NPC477924
0.8333	Intermediate Similarity	NPC470711
0.8333	Intermediate Similarity	NPC40394
0.8333	Intermediate Similarity	NPC34177
0.8333	Intermediate Similarity	NPC470758
0.8333	Intermediate Similarity	NPC130136
0.8333	Intermediate Similarity	NPC472805
0.8333	Intermediate Similarity	NPC101475
0.8333	Intermediate Similarity	NPC90979
0.8333	Intermediate Similarity	NPC91594
0.8313	Intermediate Similarity	NPC299068
0.8313	Intermediate Similarity	NPC237344
0.8313	Intermediate Similarity	NPC261266
0.8313	Intermediate Similarity	NPC201273
0.8313	Intermediate Similarity	NPC139724
0.8313	Intermediate Similarity	NPC24277
0.8313	Intermediate Similarity	NPC71520
0.8313	Intermediate Similarity	NPC6391
0.8313	Intermediate Similarity	NPC269058
0.8312	Intermediate Similarity	NPC138374
0.8312	Intermediate Similarity	NPC477923
0.8312	Intermediate Similarity	NPC34700
0.8312	Intermediate Similarity	NPC66566
0.8293	Intermediate Similarity	NPC124172
0.8272	Intermediate Similarity	NPC296701
0.8272	Intermediate Similarity	NPC218616
0.8272	Intermediate Similarity	NPC50964
0.8267	Intermediate Similarity	NPC145498
0.825	Intermediate Similarity	NPC236237
0.825	Intermediate Similarity	NPC102253
0.825	Intermediate Similarity	NPC26117
0.825	Intermediate Similarity	NPC13554
0.825	Intermediate Similarity	NPC322313
0.8235	Intermediate Similarity	NPC109744
0.8228	Intermediate Similarity	NPC302041
0.8228	Intermediate Similarity	NPC300499
0.8228	Intermediate Similarity	NPC31828
0.8228	Intermediate Similarity	NPC65897
0.8228	Intermediate Similarity	NPC85346
0.8228	Intermediate Similarity	NPC275910
0.8228	Intermediate Similarity	NPC72507
0.8214	Intermediate Similarity	NPC304083
0.8205	Intermediate Similarity	NPC120098
0.8205	Intermediate Similarity	NPC27765
0.8205	Intermediate Similarity	NPC189883
0.8205	Intermediate Similarity	NPC107059
0.8205	Intermediate Similarity	NPC240604
0.8205	Intermediate Similarity	NPC122418
0.8205	Intermediate Similarity	NPC253190
0.8205	Intermediate Similarity	NPC265328
0.8205	Intermediate Similarity	NPC134330
0.8205	Intermediate Similarity	NPC30590
0.8205	Intermediate Similarity	NPC63958
0.8205	Intermediate Similarity	NPC106364
0.8205	Intermediate Similarity	NPC290598
0.8205	Intermediate Similarity	NPC113733
0.8205	Intermediate Similarity	NPC321381
0.8205	Intermediate Similarity	NPC300324
0.8205	Intermediate Similarity	NPC321016
0.8205	Intermediate Similarity	NPC265588
0.8205	Intermediate Similarity	NPC470749
0.8205	Intermediate Similarity	NPC129165
0.8182	Intermediate Similarity	NPC306727
0.8171	Intermediate Similarity	NPC82623
0.8171	Intermediate Similarity	NPC134481
0.8171	Intermediate Similarity	NPC470558
0.8148	Intermediate Similarity	NPC116202
0.8148	Intermediate Similarity	NPC474531
0.8148	Intermediate Similarity	NPC23852
0.8148	Intermediate Similarity	NPC209620
0.814	Intermediate Similarity	NPC3345
0.814	Intermediate Similarity	NPC80561
0.814	Intermediate Similarity	NPC291484
0.814	Intermediate Similarity	NPC11216
0.814	Intermediate Similarity	NPC329596
0.814	Intermediate Similarity	NPC204188
0.8125	Intermediate Similarity	NPC475727
0.8125	Intermediate Similarity	NPC80297
0.8125	Intermediate Similarity	NPC1319
0.8125	Intermediate Similarity	NPC116119
0.8125	Intermediate Similarity	NPC472742
0.8125	Intermediate Similarity	NPC476316
0.8118	Intermediate Similarity	NPC475605
0.8118	Intermediate Similarity	NPC212596
0.8118	Intermediate Similarity	NPC4574
0.8101	Intermediate Similarity	NPC155986
0.8101	Intermediate Similarity	NPC214570
0.8101	Intermediate Similarity	NPC318495
0.8101	Intermediate Similarity	NPC202540
0.8101	Intermediate Similarity	NPC198968
0.8095	Intermediate Similarity	NPC94462
0.8077	Intermediate Similarity	NPC471723
0.8077	Intermediate Similarity	NPC257347
0.8077	Intermediate Similarity	NPC22105
0.8077	Intermediate Similarity	NPC304309
0.8077	Intermediate Similarity	NPC141071
0.8077	Intermediate Similarity	NPC162742
0.8077	Intermediate Similarity	NPC288035
0.8077	Intermediate Similarity	NPC136188
0.8077	Intermediate Similarity	NPC134847
0.8077	Intermediate Similarity	NPC285893
0.8077	Intermediate Similarity	NPC28657
0.8077	Intermediate Similarity	NPC32832
0.8077	Intermediate Similarity	NPC230301
0.8072	Intermediate Similarity	NPC205845
0.8072	Intermediate Similarity	NPC238992
0.8052	Intermediate Similarity	NPC68443
0.8049	Intermediate Similarity	NPC470614
0.8049	Intermediate Similarity	NPC1272
0.8049	Intermediate Similarity	NPC49964
0.8049	Intermediate Similarity	NPC30166
0.8049	Intermediate Similarity	NPC101462
0.8049	Intermediate Similarity	NPC47763
0.8046	Intermediate Similarity	NPC41554
0.8046	Intermediate Similarity	NPC275671
0.8046	Intermediate Similarity	NPC97404
0.8046	Intermediate Similarity	NPC473167
0.8026	Intermediate Similarity	NPC92801
0.8026	Intermediate Similarity	NPC45296
0.8025	Intermediate Similarity	NPC209944
0.8025	Intermediate Similarity	NPC71535
0.8025	Intermediate Similarity	NPC234193
0.8025	Intermediate Similarity	NPC475679
0.8025	Intermediate Similarity	NPC78545
0.8025	Intermediate Similarity	NPC47149
0.8025	Intermediate Similarity	NPC164840
0.8025	Intermediate Similarity	NPC236112
0.8025	Intermediate Similarity	NPC295131
0.8025	Intermediate Similarity	NPC241290
0.8023	Intermediate Similarity	NPC101886
0.8023	Intermediate Similarity	NPC470361
0.8023	Intermediate Similarity	NPC105495
0.8023	Intermediate Similarity	NPC138974

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 NPC148977 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1890
0.2-0.3	4238
0.3-0.4	2001
0.4-0.5	472
0.5-0.6	208
0.6-0.7	136
0.7-0.8	29
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
0.8354	Intermediate Similarity	NPD7645	Phase 2
0.825	Intermediate Similarity	NPD7525	Registered
0.8077	Intermediate Similarity	NPD7339	Approved
0.8077	Intermediate Similarity	NPD6942	Approved
0.7975	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6929	Approved
0.7654	Intermediate Similarity	NPD6932	Approved
0.759	Intermediate Similarity	NPD7332	Phase 2
0.759	Intermediate Similarity	NPD6931	Approved
0.759	Intermediate Similarity	NPD6930	Phase 2
0.7561	Intermediate Similarity	NPD7145	Approved
0.75	Intermediate Similarity	NPD6924	Approved
0.75	Intermediate Similarity	NPD6926	Approved
0.7468	Intermediate Similarity	NPD7151	Approved
0.7468	Intermediate Similarity	NPD7150	Approved
0.7468	Intermediate Similarity	NPD7152	Approved
0.7442	Intermediate Similarity	NPD4786	Approved
0.7439	Intermediate Similarity	NPD6925	Approved
0.7439	Intermediate Similarity	NPD5776	Phase 2
0.7412	Intermediate Similarity	NPD3667	Approved
0.7386	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7509	Discontinued
0.7381	Intermediate Similarity	NPD7514	Phase 3
0.7342	Intermediate Similarity	NPD7143	Approved
0.7342	Intermediate Similarity	NPD7144	Approved
0.7326	Intermediate Similarity	NPD6695	Phase 3
0.7317	Intermediate Similarity	NPD6933	Approved
0.7294	Intermediate Similarity	NPD6902	Approved
0.7294	Intermediate Similarity	NPD6898	Phase 1
0.7284	Intermediate Similarity	NPD4785	Approved
0.7284	Intermediate Similarity	NPD4784	Approved
0.7273	Intermediate Similarity	NPD3618	Phase 1
0.7262	Intermediate Similarity	NPD6683	Phase 2
0.7253	Intermediate Similarity	NPD6079	Approved
0.7241	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5328	Approved
0.7215	Intermediate Similarity	NPD6922	Approved
0.7215	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6923	Approved
0.7195	Intermediate Similarity	NPD8264	Approved
0.7176	Intermediate Similarity	NPD4748	Discontinued
0.7159	Intermediate Similarity	NPD6893	Approved
0.7158	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7639	Approved
0.7083	Intermediate Similarity	NPD7640	Approved
0.7065	Intermediate Similarity	NPD7515	Phase 2
0.7037	Intermediate Similarity	NPD4243	Approved
0.7	Intermediate Similarity	NPD7750	Discontinued
0.7	Intermediate Similarity	NPD7524	Approved
0.6966	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD3665	Phase 1
0.6854	Remote Similarity	NPD3666	Approved
0.6854	Remote Similarity	NPD3133	Approved
0.6809	Remote Similarity	NPD4202	Approved
0.6786	Remote Similarity	NPD3703	Phase 2
0.6774	Remote Similarity	NPD7136	Phase 2
0.6771	Remote Similarity	NPD5221	Approved
0.6771	Remote Similarity	NPD5222	Approved
0.6771	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6114	Approved
0.6744	Remote Similarity	NPD6697	Approved
0.6744	Remote Similarity	NPD6115	Approved
0.6744	Remote Similarity	NPD6118	Approved
0.6737	Remote Similarity	NPD7748	Approved
0.6735	Remote Similarity	NPD5286	Approved
0.6735	Remote Similarity	NPD4696	Approved
0.6735	Remote Similarity	NPD5285	Approved
0.6707	Remote Similarity	NPD4787	Phase 1
0.6702	Remote Similarity	NPD7087	Discontinued
0.6701	Remote Similarity	NPD4755	Approved
0.6701	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD3668	Phase 3
0.6667	Remote Similarity	NPD4195	Approved
0.6633	Remote Similarity	NPD5290	Discontinued
0.6632	Remote Similarity	NPD6399	Phase 3
0.6627	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5225	Approved
0.66	Remote Similarity	NPD5226	Approved
0.66	Remote Similarity	NPD7632	Discontinued
0.66	Remote Similarity	NPD4633	Approved
0.66	Remote Similarity	NPD5211	Phase 2
0.66	Remote Similarity	NPD5224	Approved
0.6598	Remote Similarity	NPD4697	Phase 3
0.6588	Remote Similarity	NPD4190	Phase 3
0.6588	Remote Similarity	NPD5275	Approved
0.6585	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4700	Approved
0.6535	Remote Similarity	NPD5174	Approved
0.6535	Remote Similarity	NPD5175	Approved
0.6531	Remote Similarity	NPD7902	Approved
0.6526	Remote Similarity	NPD7637	Suspended
0.6512	Remote Similarity	NPD6117	Approved
0.65	Remote Similarity	NPD5223	Approved
0.6489	Remote Similarity	NPD4753	Phase 2
0.6476	Remote Similarity	NPD4634	Approved
0.6471	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5141	Approved
0.6465	Remote Similarity	NPD4225	Approved
0.6442	Remote Similarity	NPD6881	Approved
0.6442	Remote Similarity	NPD6899	Approved
0.6437	Remote Similarity	NPD6116	Phase 1
0.6408	Remote Similarity	NPD6402	Approved
0.6408	Remote Similarity	NPD7128	Approved
0.6408	Remote Similarity	NPD5739	Approved
0.6408	Remote Similarity	NPD6675	Approved
0.6404	Remote Similarity	NPD6928	Phase 2
0.6374	Remote Similarity	NPD4788	Approved
0.6354	Remote Similarity	NPD6411	Approved
0.6354	Remote Similarity	NPD8034	Phase 2
0.6354	Remote Similarity	NPD8035	Phase 2
0.6346	Remote Similarity	NPD5697	Approved
0.6344	Remote Similarity	NPD4519	Discontinued
0.6344	Remote Similarity	NPD5279	Phase 3
0.6344	Remote Similarity	NPD4623	Approved
0.6344	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD4159	Approved
0.6327	Remote Similarity	NPD5210	Approved
0.6327	Remote Similarity	NPD4629	Approved
0.6321	Remote Similarity	NPD6883	Approved
0.6321	Remote Similarity	NPD7290	Approved
0.6321	Remote Similarity	NPD7102	Approved
0.631	Remote Similarity	NPD4244	Approved
0.631	Remote Similarity	NPD4245	Approved
0.6286	Remote Similarity	NPD7320	Approved
0.6286	Remote Similarity	NPD4730	Approved
0.6286	Remote Similarity	NPD4729	Approved
0.6264	Remote Similarity	NPD4221	Approved
0.6264	Remote Similarity	NPD4223	Phase 3
0.6262	Remote Similarity	NPD8130	Phase 1
0.6262	Remote Similarity	NPD6650	Approved
0.6262	Remote Similarity	NPD6847	Approved
0.6262	Remote Similarity	NPD6649	Approved
0.6262	Remote Similarity	NPD6869	Approved
0.6262	Remote Similarity	NPD6617	Approved
0.625	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD4768	Approved
0.6237	Remote Similarity	NPD5329	Approved
0.6226	Remote Similarity	NPD6012	Approved
0.6226	Remote Similarity	NPD6372	Approved
0.6226	Remote Similarity	NPD6013	Approved
0.6226	Remote Similarity	NPD6014	Approved
0.6226	Remote Similarity	NPD6373	Approved
0.6224	Remote Similarity	NPD7900	Approved
0.6224	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4695	Discontinued
0.6216	Remote Similarity	NPD7328	Approved
0.6216	Remote Similarity	NPD7327	Approved
0.6214	Remote Similarity	NPD4754	Approved
0.6211	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6882	Approved
0.6204	Remote Similarity	NPD8297	Approved
0.62	Remote Similarity	NPD6083	Phase 2
0.62	Remote Similarity	NPD6084	Phase 2
0.6195	Remote Similarity	NPD8033	Approved
0.619	Remote Similarity	NPD6412	Phase 2
0.619	Remote Similarity	NPD5701	Approved
0.619	Remote Similarity	NPD3698	Phase 2
0.618	Remote Similarity	NPD3617	Approved
0.617	Remote Similarity	NPD7334	Approved
0.617	Remote Similarity	NPD5330	Approved
0.617	Remote Similarity	NPD7146	Approved
0.617	Remote Similarity	NPD6409	Approved
0.617	Remote Similarity	NPD6684	Approved
0.617	Remote Similarity	NPD7521	Approved
0.6168	Remote Similarity	NPD5250	Approved
0.6168	Remote Similarity	NPD5249	Phase 3
0.6168	Remote Similarity	NPD5248	Approved
0.6168	Remote Similarity	NPD5251	Approved
0.6168	Remote Similarity	NPD5247	Approved
0.6163	Remote Similarity	NPD4732	Discontinued
0.6161	Remote Similarity	NPD7516	Approved
0.6147	Remote Similarity	NPD4632	Approved
0.6146	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6101	Approved
0.6146	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6011	Approved
0.6132	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD5168	Approved
0.6132	Remote Similarity	NPD5128	Approved
0.6129	Remote Similarity	NPD4197	Approved
0.6126	Remote Similarity	NPD7115	Discovery
0.6125	Remote Similarity	NPD368	Approved
0.6122	Remote Similarity	NPD5778	Approved
0.6122	Remote Similarity	NPD5779	Approved
0.6118	Remote Similarity	NPD4789	Approved
0.6111	Remote Similarity	NPD5217	Approved
0.6111	Remote Similarity	NPD5215	Approved
0.6111	Remote Similarity	NPD5216	Approved
0.6106	Remote Similarity	NPD6054	Approved
0.6106	Remote Similarity	NPD8377	Approved
0.6106	Remote Similarity	NPD8294	Approved
0.6075	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5360	Phase 3
0.6071	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD1696	Phase 3
0.6053	Remote Similarity	NPD8378	Approved

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