NPASS Compound

Structure

CID114651 OpenBabel06191715472D 21 22 0 0 1 0 0 0 0 0999 V2000 -2.4969 -0.7498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5991 2.5373 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 -0.5000 0.8660 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 -1.5446 0.8918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7185 0.2914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1116 1.3426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1981 -0.8053 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 -0.6231 -1.0503 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 0.0983 1.4402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5935 -0.3211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5187 1.5405 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 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5981 1.0647 0.0000 C 0 0 2 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3727 1.6972 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 9 11 1 0 0 0 0 9 14 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 16 19 2 0 0 0 0 17 11 1 1 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 21 1 1 0 0 0 19 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	338.244
LogP:	5.409
LogD:	4.391
LogS:	-5.366
# Rotatable Bonds:	0
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.578
Synthetic Accessibility Score:	5.291
Fsp3:	0.7
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:	-4.766
MDCK Permeability:	1.6742147636250593e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.764
30% Bioavailability (F30%):	0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.795
Plasma Protein Binding (PPB):	95.27899932861328%
Volume Distribution (VD):	1.779
Pgp-substrate:	1.5152217149734497%

ADMET: Metabolism

CYP1A2-inhibitor:	0.211
CYP1A2-substrate:	0.471
CYP2C19-inhibitor:	0.2
CYP2C19-substrate:	0.18
CYP2C9-inhibitor:	0.279
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.055
CYP2D6-substrate:	0.688
CYP3A4-inhibitor:	0.161
CYP3A4-substrate:	0.233

ADMET: Excretion

Clearance (CL):	5.698
Half-life (T1/2):	0.049

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.16
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.758
Carcinogencity:	0.179
Eye Corrosion:	0.314
Eye Irritation:	0.948
Respiratory Toxicity:	0.059

Download Data

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

Natural Product: NPC114651

Natural Product ID:	NPC114651
*Common Name:**	Cespitularin C
IUPAC Name:	(1R,7E,10R)-8,12,15,15-tetramethyl-4-methylidenebicyclo[9.3.1]pentadeca-7,11-dien-10-ol
Synonyms:	Cespitularin C
Standard InCHIKey:	BVJVBWNCZZIHMV-ZGOKVMRMSA-N
Standard InCHI:	InChI=1S/C20H32O/c1-14-7-6-8-15(2)13-18(21)19-16(3)10-12-17(11-9-14)20(19,4)5/h8,17-18,21H,1,6-7,9-13H2,2-5H3/b15-8+/t17-,18-/m1/s1
SMILES:	C=C1CC/C=C(C)/C[C@H](C2=C(C)CC[C@@H](CC1)C2(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491387
PubChem CID:	10017010
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
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398538]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933873]
NPO22004	Cystodytes solitus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18484775]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19061391]
NPO24805	Thorecta reticulata	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21513294]
NPO25343	Tanacetum microphyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25343	Tanacetum microphyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5278	Acacia cyperophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11177	0ctiluca scintillans	Species	0ctilucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24616	Ottonia vahlii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5543	Persicaria tomentosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25205	Thymus borgiae	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3706	Hedypnois rhagadioloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25343	Tanacetum microphyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24805	Thorecta reticulata	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24435	Beschorneria bracteata	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25684	Fagus dombeyi	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25631	Picris kamtschatica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25606	Aster patagonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22004	Cystodytes solitus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25314	Usnea ceratina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25655	Pseudocyphellaria granulata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23999	Rhipidothuria racowitzai	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2404	Heterophragma quadriloculare	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6639	Flagelloscypha pilatii	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25427	Solanum vespertilio	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24482	Phyllanthus oxyphyllus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25516	Dahlia sherffii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25452	Crucigenia apiculata	Species	Scenedesmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28702	Cyclolepis genistoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23333	Michelia excelsa	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25485	Agathosma lanceolata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20428	Debregeasia salicifolia	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19210	Quercus lusitanica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25061	Lactarius glyciosmus	Species	Russulaceae	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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.01	ug ml-1	PMID[452696]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.12	ug ml-1	PMID[452696]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	8.86	ug ml-1	PMID[452696]

☑ 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 NPC114651 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	165
0.1-0.2	1669
0.2-0.3	9218
0.3-0.4	15894
0.4-0.5	8244
0.5-0.6	5463
0.6-0.7	1594
0.7-0.8	380
0.8-0.85	53
0.85-0.9	14
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9242	High Similarity	NPC34834
0.9206	High Similarity	NPC290367
0.8939	High Similarity	NPC208999
0.8923	High Similarity	NPC202017
0.8806	High Similarity	NPC471560
0.8806	High Similarity	NPC474248
0.8732	High Similarity	NPC91594
0.8657	High Similarity	NPC96484
0.8615	High Similarity	NPC107540
0.8615	High Similarity	NPC96793
0.8615	High Similarity	NPC323424
0.8611	High Similarity	NPC167891
0.8611	High Similarity	NPC83351
0.8592	High Similarity	NPC244488
0.8592	High Similarity	NPC265588
0.8592	High Similarity	NPC247325
0.8571	High Similarity	NPC122239
0.8529	High Similarity	NPC473893
0.8507	High Similarity	NPC68703
0.8507	High Similarity	NPC69649
0.8507	High Similarity	NPC171225
0.8493	Intermediate Similarity	NPC28862
0.8493	Intermediate Similarity	NPC109546
0.8493	Intermediate Similarity	NPC81306
0.8493	Intermediate Similarity	NPC84694
0.8493	Intermediate Similarity	NPC47982
0.8493	Intermediate Similarity	NPC143182
0.8451	Intermediate Similarity	NPC313179
0.8451	Intermediate Similarity	NPC69383
0.8451	Intermediate Similarity	NPC171148
0.8429	Intermediate Similarity	NPC130665
0.8429	Intermediate Similarity	NPC471799
0.8406	Intermediate Similarity	NPC145498
0.8387	Intermediate Similarity	NPC48891
0.8378	Intermediate Similarity	NPC234193
0.8358	Intermediate Similarity	NPC286669
0.8358	Intermediate Similarity	NPC476039
0.8358	Intermediate Similarity	NPC279434
0.8358	Intermediate Similarity	NPC326310
0.8358	Intermediate Similarity	NPC222366
0.8356	Intermediate Similarity	NPC474216
0.8356	Intermediate Similarity	NPC476314
0.8333	Intermediate Similarity	NPC309300
0.8333	Intermediate Similarity	NPC225415
0.831	Intermediate Similarity	NPC201048
0.831	Intermediate Similarity	NPC476366
0.831	Intermediate Similarity	NPC471797
0.831	Intermediate Similarity	NPC306727
0.8308	Intermediate Similarity	NPC475251
0.8286	Intermediate Similarity	NPC242001
0.8286	Intermediate Similarity	NPC477792
0.8267	Intermediate Similarity	NPC476646
0.8267	Intermediate Similarity	NPC209620
0.8267	Intermediate Similarity	NPC264245
0.8267	Intermediate Similarity	NPC23852
0.8254	Intermediate Similarity	NPC11130
0.8243	Intermediate Similarity	NPC30986
0.8243	Intermediate Similarity	NPC209430
0.8235	Intermediate Similarity	NPC197805
0.8219	Intermediate Similarity	NPC470711
0.8219	Intermediate Similarity	NPC470758
0.8209	Intermediate Similarity	NPC163678
0.8209	Intermediate Similarity	NPC19569
0.8194	Intermediate Similarity	NPC136188
0.8194	Intermediate Similarity	NPC230301
0.8194	Intermediate Similarity	NPC28657
0.8194	Intermediate Similarity	NPC22105
0.8194	Intermediate Similarity	NPC32832
0.8194	Intermediate Similarity	NPC162742
0.8194	Intermediate Similarity	NPC285893
0.8194	Intermediate Similarity	NPC134847
0.8194	Intermediate Similarity	NPC304309
0.8194	Intermediate Similarity	NPC288035
0.8182	Intermediate Similarity	NPC473759
0.8182	Intermediate Similarity	NPC474155
0.8169	Intermediate Similarity	NPC182717
0.8169	Intermediate Similarity	NPC474140
0.8169	Intermediate Similarity	NPC220939
0.8169	Intermediate Similarity	NPC265485
0.8169	Intermediate Similarity	NPC474743
0.8158	Intermediate Similarity	NPC50964
0.8158	Intermediate Similarity	NPC101462
0.8158	Intermediate Similarity	NPC49964
0.8158	Intermediate Similarity	NPC189972
0.8154	Intermediate Similarity	NPC66020
0.8154	Intermediate Similarity	NPC471081
0.8143	Intermediate Similarity	NPC92801
0.8143	Intermediate Similarity	NPC189745
0.8133	Intermediate Similarity	NPC295131
0.8133	Intermediate Similarity	NPC241290
0.8133	Intermediate Similarity	NPC164840
0.8133	Intermediate Similarity	NPC96362
0.8133	Intermediate Similarity	NPC209944
0.8125	Intermediate Similarity	NPC226848
0.8116	Intermediate Similarity	NPC471238
0.8116	Intermediate Similarity	NPC216460
0.8108	Intermediate Similarity	NPC475994
0.8108	Intermediate Similarity	NPC473943
0.8088	Intermediate Similarity	NPC250977
0.8088	Intermediate Similarity	NPC267027
0.8082	Intermediate Similarity	NPC253190
0.8082	Intermediate Similarity	NPC106364
0.8082	Intermediate Similarity	NPC107059
0.8082	Intermediate Similarity	NPC240604
0.8082	Intermediate Similarity	NPC321381
0.8082	Intermediate Similarity	NPC113733
0.8082	Intermediate Similarity	NPC321016
0.8082	Intermediate Similarity	NPC300324
0.8082	Intermediate Similarity	NPC470749
0.8056	Intermediate Similarity	NPC469533
0.8056	Intermediate Similarity	NPC469534
0.8056	Intermediate Similarity	NPC243342
0.8056	Intermediate Similarity	NPC100334
0.8056	Intermediate Similarity	NPC469593
0.8056	Intermediate Similarity	NPC477138
0.8052	Intermediate Similarity	NPC474634
0.8052	Intermediate Similarity	NPC317458
0.8052	Intermediate Similarity	NPC470384
0.8052	Intermediate Similarity	NPC475789
0.803	Intermediate Similarity	NPC207007
0.803	Intermediate Similarity	NPC68679
0.803	Intermediate Similarity	NPC321867
0.8028	Intermediate Similarity	NPC23954
0.8028	Intermediate Similarity	NPC167706
0.8028	Intermediate Similarity	NPC110799
0.8026	Intermediate Similarity	NPC82986
0.8026	Intermediate Similarity	NPC7505
0.8026	Intermediate Similarity	NPC474731
0.8026	Intermediate Similarity	NPC474759
0.8026	Intermediate Similarity	NPC474752
0.8026	Intermediate Similarity	NPC47761
0.8026	Intermediate Similarity	NPC474683
0.8	Intermediate Similarity	NPC475931
0.8	Intermediate Similarity	NPC242767
0.7973	Intermediate Similarity	NPC198968
0.7973	Intermediate Similarity	NPC471798
0.7973	Intermediate Similarity	NPC34019
0.7973	Intermediate Similarity	NPC477425
0.7973	Intermediate Similarity	NPC474826
0.7973	Intermediate Similarity	NPC155986
0.7973	Intermediate Similarity	NPC318495
0.7973	Intermediate Similarity	NPC477426
0.7973	Intermediate Similarity	NPC477427
0.7949	Intermediate Similarity	NPC185568
0.7949	Intermediate Similarity	NPC238485
0.7949	Intermediate Similarity	NPC205845
0.7945	Intermediate Similarity	NPC141071
0.7945	Intermediate Similarity	NPC471723
0.7945	Intermediate Similarity	NPC66566
0.7945	Intermediate Similarity	NPC257347
0.7945	Intermediate Similarity	NPC477923
0.7945	Intermediate Similarity	NPC291503
0.7937	Intermediate Similarity	NPC148163
0.7937	Intermediate Similarity	NPC251666
0.7937	Intermediate Similarity	NPC148216
0.7937	Intermediate Similarity	NPC130209
0.7937	Intermediate Similarity	NPC232247
0.7922	Intermediate Similarity	NPC87489
0.7922	Intermediate Similarity	NPC202389
0.7922	Intermediate Similarity	NPC471408
0.791	Intermediate Similarity	NPC81615
0.791	Intermediate Similarity	NPC473508
0.791	Intermediate Similarity	NPC83200
0.791	Intermediate Similarity	NPC174956
0.7895	Intermediate Similarity	NPC474592
0.7879	Intermediate Similarity	NPC99487
0.7879	Intermediate Similarity	NPC240506
0.7867	Intermediate Similarity	NPC477514
0.7867	Intermediate Similarity	NPC76931
0.7867	Intermediate Similarity	NPC474989
0.7867	Intermediate Similarity	NPC275910
0.7867	Intermediate Similarity	NPC18603
0.7867	Intermediate Similarity	NPC11908
0.7867	Intermediate Similarity	NPC297996
0.7867	Intermediate Similarity	NPC307965
0.7867	Intermediate Similarity	NPC470396
0.7867	Intermediate Similarity	NPC22955
0.7867	Intermediate Similarity	NPC99168
0.7867	Intermediate Similarity	NPC477522
0.7867	Intermediate Similarity	NPC87604
0.7857	Intermediate Similarity	NPC32055
0.7857	Intermediate Similarity	NPC117804
0.7857	Intermediate Similarity	NPC224532
0.7857	Intermediate Similarity	NPC160209
0.7848	Intermediate Similarity	NPC266511
0.7848	Intermediate Similarity	NPC274448
0.7846	Intermediate Similarity	NPC155025
0.7838	Intermediate Similarity	NPC30590
0.7838	Intermediate Similarity	NPC27765
0.7838	Intermediate Similarity	NPC265328
0.7838	Intermediate Similarity	NPC470362
0.7838	Intermediate Similarity	NPC46160
0.7838	Intermediate Similarity	NPC129165
0.7838	Intermediate Similarity	NPC134330
0.7838	Intermediate Similarity	NPC477925
0.7838	Intermediate Similarity	NPC290598
0.7838	Intermediate Similarity	NPC96319
0.7838	Intermediate Similarity	NPC189883
0.7838	Intermediate Similarity	NPC122418
0.7838	Intermediate Similarity	NPC120098

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 NPC114651 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	2322
0.2-0.3	3997
0.3-0.4	1889
0.4-0.5	530
0.5-0.6	161
0.6-0.7	73
0.7-0.8	7
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8451	Intermediate Similarity	NPD8264	Approved
0.8194	Intermediate Similarity	NPD7339	Approved
0.8194	Intermediate Similarity	NPD6942	Approved
0.803	Intermediate Similarity	NPD368	Approved
0.7937	Intermediate Similarity	NPD342	Phase 1
0.7838	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD6922	Approved
0.7746	Intermediate Similarity	NPD6923	Approved
0.7639	Intermediate Similarity	NPD7143	Approved
0.7639	Intermediate Similarity	NPD7144	Approved
0.7632	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6926	Approved
0.7568	Intermediate Similarity	NPD6924	Approved
0.7538	Intermediate Similarity	NPD4219	Approved
0.7534	Intermediate Similarity	NPD7151	Approved
0.7534	Intermediate Similarity	NPD7150	Approved
0.7534	Intermediate Similarity	NPD7152	Approved
0.7532	Intermediate Similarity	NPD6929	Approved
0.7532	Intermediate Similarity	NPD7645	Phase 2
0.75	Intermediate Similarity	NPD5776	Phase 2
0.75	Intermediate Similarity	NPD6925	Approved
0.7439	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7332	Phase 2
0.7436	Intermediate Similarity	NPD6930	Phase 2
0.7436	Intermediate Similarity	NPD6931	Approved
0.7436	Intermediate Similarity	NPD7514	Phase 3
0.7403	Intermediate Similarity	NPD7145	Approved
0.7368	Intermediate Similarity	NPD6933	Approved
0.7342	Intermediate Similarity	NPD6902	Approved
0.7333	Intermediate Similarity	NPD4785	Approved
0.7333	Intermediate Similarity	NPD4784	Approved
0.7297	Intermediate Similarity	NPD4243	Approved
0.7284	Intermediate Similarity	NPD4786	Approved
0.725	Intermediate Similarity	NPD3667	Approved
0.7215	Intermediate Similarity	NPD7525	Registered
0.716	Intermediate Similarity	NPD6695	Phase 3
0.7125	Intermediate Similarity	NPD6898	Phase 1
0.7073	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6932	Approved
0.7	Intermediate Similarity	NPD7509	Discontinued
0.6988	Remote Similarity	NPD6893	Approved
0.6875	Remote Similarity	NPD6683	Phase 2
0.6867	Remote Similarity	NPD3133	Approved
0.6867	Remote Similarity	NPD3666	Approved
0.6867	Remote Similarity	NPD3665	Phase 1
0.6824	Remote Similarity	NPD7750	Discontinued
0.6824	Remote Similarity	NPD7524	Approved
0.6795	Remote Similarity	NPD5275	Approved
0.6795	Remote Similarity	NPD4190	Phase 3
0.679	Remote Similarity	NPD4748	Discontinued
0.6786	Remote Similarity	NPD1696	Phase 3
0.6753	Remote Similarity	NPD4732	Discontinued
0.675	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4822	Approved
0.6585	Remote Similarity	NPD4819	Approved
0.6585	Remote Similarity	NPD4820	Approved
0.6585	Remote Similarity	NPD4821	Approved
0.6548	Remote Similarity	NPD5331	Approved
0.6548	Remote Similarity	NPD5332	Approved
0.6548	Remote Similarity	NPD5362	Discontinued
0.6543	Remote Similarity	NPD4268	Approved
0.6543	Remote Similarity	NPD4271	Approved
0.6517	Remote Similarity	NPD7637	Suspended
0.6517	Remote Similarity	NPD7515	Phase 2
0.6517	Remote Similarity	NPD6079	Approved
0.6517	Remote Similarity	NPD7087	Discontinued
0.6512	Remote Similarity	NPD4623	Approved
0.6512	Remote Similarity	NPD5279	Phase 3
0.6512	Remote Similarity	NPD4519	Discontinued
0.6508	Remote Similarity	NPD4265	Approved
0.6506	Remote Similarity	NPD4790	Discontinued
0.6471	Remote Similarity	NPD3668	Phase 3
0.6463	Remote Similarity	NPD4195	Approved
0.6444	Remote Similarity	NPD5778	Approved
0.6444	Remote Similarity	NPD5779	Approved
0.6444	Remote Similarity	NPD6399	Phase 3
0.6429	Remote Similarity	NPD4270	Approved
0.6429	Remote Similarity	NPD4269	Approved
0.6404	Remote Similarity	NPD7136	Phase 2
0.6386	Remote Similarity	NPD4695	Discontinued
0.6386	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7639	Approved
0.6383	Remote Similarity	NPD7640	Approved
0.6353	Remote Similarity	NPD7154	Phase 3
0.6333	Remote Similarity	NPD6411	Approved
0.6301	Remote Similarity	NPD4194	Approved
0.6301	Remote Similarity	NPD4191	Approved
0.6301	Remote Similarity	NPD4192	Approved
0.6301	Remote Similarity	NPD4193	Approved
0.6292	Remote Similarity	NPD6051	Approved
0.6292	Remote Similarity	NPD4753	Phase 2
0.6277	Remote Similarity	NPD7638	Approved
0.6277	Remote Similarity	NPD4225	Approved
0.6264	Remote Similarity	NPD4202	Approved
0.6235	Remote Similarity	NPD4223	Phase 3
0.6235	Remote Similarity	NPD4221	Approved
0.6222	Remote Similarity	NPD5785	Approved
0.6207	Remote Similarity	NPD5329	Approved
0.6207	Remote Similarity	NPD5363	Approved
0.6196	Remote Similarity	NPD7748	Approved
0.619	Remote Similarity	NPD4252	Approved
0.6184	Remote Similarity	NPD7331	Phase 2
0.6173	Remote Similarity	NPD8039	Approved
0.6136	Remote Similarity	NPD7521	Approved
0.6136	Remote Similarity	NPD5330	Approved
0.6136	Remote Similarity	NPD6409	Approved
0.6136	Remote Similarity	NPD6684	Approved
0.6136	Remote Similarity	NPD7146	Approved
0.6136	Remote Similarity	NPD5786	Approved
0.6136	Remote Similarity	NPD7334	Approved
0.6133	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6101	Approved
0.6092	Remote Similarity	NPD4197	Approved
0.6082	Remote Similarity	NPD5211	Phase 2
0.6064	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5222	Approved
0.6064	Remote Similarity	NPD5221	Approved
0.6064	Remote Similarity	NPD4697	Phase 3
0.6023	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD5173	Approved
0.6	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6903	Approved
0.6	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD4755	Approved
0.6	Remote Similarity	NPD6084	Phase 2
0.5977	Remote Similarity	NPD6110	Phase 1
0.5977	Remote Similarity	NPD4788	Approved
0.596	Remote Similarity	NPD5141	Approved
0.5957	Remote Similarity	NPD5210	Approved
0.5957	Remote Similarity	NPD4629	Approved
0.5955	Remote Similarity	NPD5690	Phase 2
0.5955	Remote Similarity	NPD4688	Approved
0.5955	Remote Similarity	NPD4689	Approved
0.5955	Remote Similarity	NPD5205	Approved
0.5955	Remote Similarity	NPD5280	Approved
0.5955	Remote Similarity	NPD4690	Approved
0.5955	Remote Similarity	NPD4138	Approved
0.5955	Remote Similarity	NPD4693	Phase 3
0.5955	Remote Similarity	NPD4694	Approved
0.5952	Remote Similarity	NPD3617	Approved
0.5949	Remote Similarity	NPD15	Approved
0.5949	Remote Similarity	NPD791	Approved
0.5946	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5290	Discontinued
0.5934	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.593	Remote Similarity	NPD5369	Approved
0.5909	Remote Similarity	NPD384	Approved
0.5909	Remote Similarity	NPD385	Approved
0.5904	Remote Similarity	NPD1346	Approved
0.59	Remote Similarity	NPD6640	Phase 3
0.589	Remote Similarity	NPD287	Approved
0.5889	Remote Similarity	NPD4250	Approved
0.5889	Remote Similarity	NPD4251	Approved
0.5876	Remote Similarity	NPD4700	Approved
0.5876	Remote Similarity	NPD5286	Approved
0.5876	Remote Similarity	NPD4696	Approved
0.5876	Remote Similarity	NPD5285	Approved
0.587	Remote Similarity	NPD6698	Approved
0.587	Remote Similarity	NPD46	Approved
0.5862	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD7341	Phase 2
0.5824	Remote Similarity	NPD4723	Approved
0.5824	Remote Similarity	NPD5737	Approved
0.5824	Remote Similarity	NPD4722	Approved
0.5824	Remote Similarity	NPD6672	Approved
0.5823	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD5223	Approved
0.5816	Remote Similarity	NPD4159	Approved
0.5816	Remote Similarity	NPD5344	Discontinued
0.5814	Remote Similarity	NPD5368	Approved
0.5806	Remote Similarity	NPD7983	Approved
0.5794	Remote Similarity	NPD7115	Discovery
0.5789	Remote Similarity	NPD5695	Phase 3
0.5781	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD4249	Approved
0.5758	Remote Similarity	NPD5226	Approved
0.5758	Remote Similarity	NPD7632	Discontinued
0.5758	Remote Similarity	NPD4633	Approved
0.5758	Remote Similarity	NPD5224	Approved
0.5758	Remote Similarity	NPD5225	Approved
0.575	Remote Similarity	NPD4137	Phase 3
0.575	Remote Similarity	NPD1082	Approved
0.5747	Remote Similarity	NPD4692	Approved
0.5747	Remote Similarity	NPD4139	Approved
0.5743	Remote Similarity	NPD6675	Approved
0.5743	Remote Similarity	NPD5739	Approved
0.5743	Remote Similarity	NPD6402	Approved
0.5743	Remote Similarity	NPD7128	Approved
0.5735	Remote Similarity	NPD8262	Approved
0.5729	Remote Similarity	NPD4792	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