NPASS Compound

Structure

NPC95958 OpenBabel07101719132D 21 24 0 0 1 0 0 0 0 0999 V2000 -4.1225 1.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7624 -0.4898 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 -2.3198 -0.8090 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 -2.0685 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 1.4781 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 -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 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 -3.4533 0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 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 -0.0000 -1.0000 0.0000 C 0 0 2 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 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 2.2321 0.8660 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 3 17 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 13 14 1 0 0 0 0 14 18 1 1 0 0 0 15 18 1 1 0 0 0 15 20 1 0 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 17 20 1 1 0 0 0 18 4 1 1 0 0 0 19 5 1 1 0 0 0 19 21 1 0 0 0 0 20 12 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.26
Volume:	329.041
LogP:	4.138
LogD:	4.524
LogS:	-5.221
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.718
Synthetic Accessibility Score:	5.265
Fsp3:	1.0
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:	-4.851
MDCK Permeability:	4.9486596253700554e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.885

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	97.44181823730469%
Volume Distribution (VD):	1.366
Pgp-substrate:	2.4471852779388428%

ADMET: Metabolism

CYP1A2-inhibitor:	0.13
CYP1A2-substrate:	0.512
CYP2C19-inhibitor:	0.167
CYP2C19-substrate:	0.935
CYP2C9-inhibitor:	0.265
CYP2C9-substrate:	0.205
CYP2D6-inhibitor:	0.061
CYP2D6-substrate:	0.182
CYP3A4-inhibitor:	0.484
CYP3A4-substrate:	0.713

ADMET: Excretion

Clearance (CL):	5.012
Half-life (T1/2):	0.324

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.053
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.056
Skin Sensitization:	0.794
Carcinogencity:	0.015
Eye Corrosion:	0.985
Eye Irritation:	0.918
Respiratory Toxicity:	0.246

Download Data

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

Natural Product: NPC95958

Natural Product ID:	NPC95958
*Common Name:**	LIXXTIXZQFXCDM-SCCUFHEXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LIXXTIXZQFXCDM-SCCUFHEXSA-N
Standard InCHI:	InChI=1S/C20H34O/c1-13(2)14-6-7-15-18(14,4)10-8-17(3)9-11-19(5,21)16-12-20(15,16)17/h13-16,21H,6-12H2,1-5H3/t14-,15-,16+,17+,18-,19-,20-/m1/s1
SMILES:	CC([C@H]1CC[C@@H]2[C@]1(C)CC[C@@]1([C@@]32C[C@H]3[C@](CC1)(C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478383
PubChem CID:	10803470
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003548] Valparane and mulinane 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
NPO22235	Azorella madreporica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9677287]
NPO22235	Azorella madreporica	Species	Apiaceae	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
IC50	1
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	184.0	ug.mL-1	PMID[556296]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	20.0	ug.mL-1	PMID[556296]

☑ 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 NPC95958 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	383
0.1-0.2	6760
0.2-0.3	18911
0.3-0.4	6830
0.4-0.5	5706
0.5-0.6	3059
0.6-0.7	859
0.7-0.8	170
0.8-0.85	15
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8852	High Similarity	NPC474380
0.8852	High Similarity	NPC473276
0.8852	High Similarity	NPC41577
0.8772	High Similarity	NPC3025
0.8689	High Similarity	NPC69149
0.8594	High Similarity	NPC470830
0.8594	High Similarity	NPC241085
0.8594	High Similarity	NPC299948
0.8571	High Similarity	NPC473230
0.8571	High Similarity	NPC475884
0.8475	Intermediate Similarity	NPC162685
0.8421	Intermediate Similarity	NPC32222
0.8421	Intermediate Similarity	NPC202146
0.8361	Intermediate Similarity	NPC71460
0.8361	Intermediate Similarity	NPC95804
0.8361	Intermediate Similarity	NPC218585
0.8361	Intermediate Similarity	NPC185547
0.8361	Intermediate Similarity	NPC148174
0.8333	Intermediate Similarity	NPC473279
0.8333	Intermediate Similarity	NPC195530
0.8305	Intermediate Similarity	NPC135438
0.8281	Intermediate Similarity	NPC48079
0.8226	Intermediate Similarity	NPC114891
0.8209	Intermediate Similarity	NPC472341
0.8209	Intermediate Similarity	NPC473238
0.8154	Intermediate Similarity	NPC472741
0.8125	Intermediate Similarity	NPC142712
0.806	Intermediate Similarity	NPC8004
0.806	Intermediate Similarity	NPC127283
0.803	Intermediate Similarity	NPC107919
0.803	Intermediate Similarity	NPC254037
0.803	Intermediate Similarity	NPC66407
0.803	Intermediate Similarity	NPC129829
0.8	Intermediate Similarity	NPC63190
0.8	Intermediate Similarity	NPC236588
0.7971	Intermediate Similarity	NPC186851
0.7931	Intermediate Similarity	NPC102336
0.7931	Intermediate Similarity	NPC36002
0.791	Intermediate Similarity	NPC282454
0.791	Intermediate Similarity	NPC192192
0.791	Intermediate Similarity	NPC231945
0.7879	Intermediate Similarity	NPC474756
0.7869	Intermediate Similarity	NPC476735
0.7846	Intermediate Similarity	NPC44122
0.7826	Intermediate Similarity	NPC145552
0.7826	Intermediate Similarity	NPC478130
0.7826	Intermediate Similarity	NPC5046
0.7826	Intermediate Similarity	NPC49168
0.7826	Intermediate Similarity	NPC254509
0.7826	Intermediate Similarity	NPC196358
0.7818	Intermediate Similarity	NPC14552
0.7812	Intermediate Similarity	NPC118937
0.7812	Intermediate Similarity	NPC167995
0.7812	Intermediate Similarity	NPC281540
0.7812	Intermediate Similarity	NPC159654
0.7794	Intermediate Similarity	NPC1340
0.7794	Intermediate Similarity	NPC131506
0.7794	Intermediate Similarity	NPC187471
0.7794	Intermediate Similarity	NPC109457
0.7794	Intermediate Similarity	NPC127094
0.7794	Intermediate Similarity	NPC157777
0.7794	Intermediate Similarity	NPC252182
0.7794	Intermediate Similarity	NPC157422
0.7794	Intermediate Similarity	NPC470071
0.7794	Intermediate Similarity	NPC100586
0.7761	Intermediate Similarity	NPC477820
0.7746	Intermediate Similarity	NPC475031
0.7714	Intermediate Similarity	NPC273366
0.7714	Intermediate Similarity	NPC200243
0.7714	Intermediate Similarity	NPC230704
0.7714	Intermediate Similarity	NPC70982
0.7692	Intermediate Similarity	NPC190827
0.7692	Intermediate Similarity	NPC243469
0.7692	Intermediate Similarity	NPC475943
0.7692	Intermediate Similarity	NPC472946
0.7681	Intermediate Similarity	NPC195489
0.7681	Intermediate Similarity	NPC153719
0.7656	Intermediate Similarity	NPC249078
0.7656	Intermediate Similarity	NPC236099
0.7656	Intermediate Similarity	NPC209686
0.7647	Intermediate Similarity	NPC232925
0.7647	Intermediate Similarity	NPC251201
0.7647	Intermediate Similarity	NPC63588
0.7639	Intermediate Similarity	NPC471769
0.7639	Intermediate Similarity	NPC147993
0.7639	Intermediate Similarity	NPC472342
0.7606	Intermediate Similarity	NPC470145
0.7571	Intermediate Similarity	NPC10476
0.7571	Intermediate Similarity	NPC477508
0.7571	Intermediate Similarity	NPC228994
0.7571	Intermediate Similarity	NPC304499
0.7571	Intermediate Similarity	NPC192501
0.7544	Intermediate Similarity	NPC127997
0.7544	Intermediate Similarity	NPC95969
0.7544	Intermediate Similarity	NPC316035
0.7536	Intermediate Similarity	NPC111234
0.7536	Intermediate Similarity	NPC478103
0.7534	Intermediate Similarity	NPC287452
0.7534	Intermediate Similarity	NPC269333
0.75	Intermediate Similarity	NPC476233
0.75	Intermediate Similarity	NPC257191
0.75	Intermediate Similarity	NPC331618
0.75	Intermediate Similarity	NPC196197
0.7465	Intermediate Similarity	NPC91387
0.7465	Intermediate Similarity	NPC317242
0.7465	Intermediate Similarity	NPC270306
0.7465	Intermediate Similarity	NPC196136
0.7465	Intermediate Similarity	NPC158208
0.7465	Intermediate Similarity	NPC243027
0.7465	Intermediate Similarity	NPC3403
0.7465	Intermediate Similarity	NPC231680
0.7429	Intermediate Similarity	NPC232112
0.7429	Intermediate Similarity	NPC470610
0.7424	Intermediate Similarity	NPC64123
0.7424	Intermediate Similarity	NPC260116
0.7424	Intermediate Similarity	NPC80463
0.7424	Intermediate Similarity	NPC230047
0.7424	Intermediate Similarity	NPC19311
0.7397	Intermediate Similarity	NPC302041
0.7397	Intermediate Similarity	NPC85346
0.7397	Intermediate Similarity	NPC65897
0.7391	Intermediate Similarity	NPC45296
0.7385	Intermediate Similarity	NPC292419
0.7385	Intermediate Similarity	NPC290791
0.7361	Intermediate Similarity	NPC163597
0.7361	Intermediate Similarity	NPC91573
0.7353	Intermediate Similarity	NPC473225
0.7333	Intermediate Similarity	NPC12933
0.7324	Intermediate Similarity	NPC62657
0.7324	Intermediate Similarity	NPC272359
0.7324	Intermediate Similarity	NPC25511
0.7324	Intermediate Similarity	NPC48795
0.7324	Intermediate Similarity	NPC475458
0.7324	Intermediate Similarity	NPC192638
0.7302	Intermediate Similarity	NPC474769
0.7302	Intermediate Similarity	NPC189290
0.7286	Intermediate Similarity	NPC320549
0.7286	Intermediate Similarity	NPC151018
0.7286	Intermediate Similarity	NPC156277
0.7286	Intermediate Similarity	NPC58057
0.7273	Intermediate Similarity	NPC128608
0.726	Intermediate Similarity	NPC11907
0.726	Intermediate Similarity	NPC23884
0.726	Intermediate Similarity	NPC128951
0.726	Intermediate Similarity	NPC185915
0.726	Intermediate Similarity	NPC477227
0.726	Intermediate Similarity	NPC212453
0.726	Intermediate Similarity	NPC133596
0.726	Intermediate Similarity	NPC192046
0.726	Intermediate Similarity	NPC105208
0.726	Intermediate Similarity	NPC302578
0.726	Intermediate Similarity	NPC474574
0.726	Intermediate Similarity	NPC64081
0.7246	Intermediate Similarity	NPC474962
0.7237	Intermediate Similarity	NPC475388
0.7222	Intermediate Similarity	NPC104387
0.7222	Intermediate Similarity	NPC240235
0.7222	Intermediate Similarity	NPC174964
0.7222	Intermediate Similarity	NPC97534
0.7222	Intermediate Similarity	NPC476424
0.7222	Intermediate Similarity	NPC185536
0.7222	Intermediate Similarity	NPC178383
0.7222	Intermediate Similarity	NPC231256
0.7222	Intermediate Similarity	NPC212733
0.7222	Intermediate Similarity	NPC212879
0.7222	Intermediate Similarity	NPC195155
0.7213	Intermediate Similarity	NPC53209
0.7206	Intermediate Similarity	NPC474221
0.7206	Intermediate Similarity	NPC101307
0.7206	Intermediate Similarity	NPC88454
0.7206	Intermediate Similarity	NPC476928
0.7206	Intermediate Similarity	NPC130459
0.7206	Intermediate Similarity	NPC478180
0.7206	Intermediate Similarity	NPC117607
0.7206	Intermediate Similarity	NPC41542
0.72	Intermediate Similarity	NPC16449
0.7183	Intermediate Similarity	NPC201373
0.7164	Intermediate Similarity	NPC477603
0.7162	Intermediate Similarity	NPC301707
0.7162	Intermediate Similarity	NPC18857
0.7162	Intermediate Similarity	NPC312328
0.7162	Intermediate Similarity	NPC42853
0.7162	Intermediate Similarity	NPC31828
0.7162	Intermediate Similarity	NPC285761
0.7162	Intermediate Similarity	NPC67657
0.7143	Intermediate Similarity	NPC82623
0.7143	Intermediate Similarity	NPC29976
0.7143	Intermediate Similarity	NPC134481
0.7143	Intermediate Similarity	NPC475728
0.7143	Intermediate Similarity	NPC150713
0.7123	Intermediate Similarity	NPC477601
0.7123	Intermediate Similarity	NPC475742
0.7123	Intermediate Similarity	NPC78067
0.7123	Intermediate Similarity	NPC472487
0.7123	Intermediate Similarity	NPC86305
0.7123	Intermediate Similarity	NPC93662
0.7123	Intermediate Similarity	NPC278091
0.7123	Intermediate Similarity	NPC4209
0.7123	Intermediate Similarity	NPC473916
0.7123	Intermediate Similarity	NPC5767

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 NPC95958 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	428
0.1-0.2	5157
0.2-0.3	2644
0.3-0.4	498
0.4-0.5	189
0.5-0.6	178
0.6-0.7	50
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.803	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD5360	Phase 3
0.7879	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4787	Phase 1
0.7286	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD4758	Discontinued
0.7286	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6117	Approved
0.7083	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4243	Approved
0.7027	Intermediate Similarity	NPD6116	Phase 1
0.7	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7525	Registered
0.6933	Remote Similarity	NPD5364	Discontinued
0.6933	Remote Similarity	NPD6118	Approved
0.6933	Remote Similarity	NPD6115	Approved
0.6933	Remote Similarity	NPD6697	Approved
0.6933	Remote Similarity	NPD6114	Approved
0.6901	Remote Similarity	NPD4789	Approved
0.6857	Remote Similarity	NPD6705	Phase 1
0.6849	Remote Similarity	NPD4785	Approved
0.6849	Remote Similarity	NPD4784	Approved
0.6812	Remote Similarity	NPD4224	Phase 2
0.6806	Remote Similarity	NPD6081	Approved
0.6757	Remote Similarity	NPD7339	Approved
0.6757	Remote Similarity	NPD6942	Approved
0.6757	Remote Similarity	NPD3703	Phase 2
0.6724	Remote Similarity	NPD386	Approved
0.6724	Remote Similarity	NPD388	Approved
0.6667	Remote Similarity	NPD4244	Approved
0.6667	Remote Similarity	NPD4245	Approved
0.661	Remote Similarity	NPD385	Approved
0.661	Remote Similarity	NPD384	Approved
0.6538	Remote Similarity	NPD6928	Phase 2
0.6533	Remote Similarity	NPD3702	Approved
0.6533	Remote Similarity	NPD5275	Approved
0.6533	Remote Similarity	NPD4190	Phase 3
0.6528	Remote Similarity	NPD3698	Phase 2
0.64	Remote Similarity	NPD6926	Approved
0.64	Remote Similarity	NPD6924	Approved
0.6341	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD4748	Discontinued
0.6282	Remote Similarity	NPD3671	Phase 1
0.6234	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD6933	Approved
0.6203	Remote Similarity	NPD4195	Approved
0.6133	Remote Similarity	NPD7152	Approved
0.6133	Remote Similarity	NPD7151	Approved
0.6133	Remote Similarity	NPD7150	Approved
0.6102	Remote Similarity	NPD367	Approved
0.6098	Remote Similarity	NPD4788	Approved
0.6081	Remote Similarity	NPD6923	Approved
0.6081	Remote Similarity	NPD6922	Approved
0.6047	Remote Similarity	NPD5328	Approved
0.6024	Remote Similarity	NPD4786	Approved
0.6	Remote Similarity	NPD7144	Approved
0.6	Remote Similarity	NPD7645	Phase 2
0.6	Remote Similarity	NPD7143	Approved
0.5977	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD6700	Approved
0.5976	Remote Similarity	NPD4223	Phase 3
0.5976	Remote Similarity	NPD4221	Approved
0.5952	Remote Similarity	NPD5329	Approved
0.5926	Remote Similarity	NPD6930	Phase 2
0.5926	Remote Similarity	NPD6931	Approved
0.5926	Remote Similarity	NPD7509	Discontinued
0.5921	Remote Similarity	NPD5777	Approved
0.5909	Remote Similarity	NPD8035	Phase 2
0.5909	Remote Similarity	NPD6702	Approved
0.5909	Remote Similarity	NPD6079	Approved
0.5909	Remote Similarity	NPD6703	Approved
0.5909	Remote Similarity	NPD8034	Phase 2
0.5882	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD3618	Phase 1
0.5875	Remote Similarity	NPD3617	Approved
0.5854	Remote Similarity	NPD4139	Approved
0.5854	Remote Similarity	NPD4692	Approved
0.5843	Remote Similarity	NPD4202	Approved
0.5833	Remote Similarity	NPD371	Approved
0.5833	Remote Similarity	NPD4197	Approved
0.5814	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD6929	Approved
0.5783	Remote Similarity	NPD3667	Approved
0.575	Remote Similarity	NPD6932	Approved
0.5714	Remote Similarity	NPD6695	Phase 3
0.5698	Remote Similarity	NPD8308	Discontinued
0.5698	Remote Similarity	NPD4693	Phase 3
0.5698	Remote Similarity	NPD4690	Approved
0.5698	Remote Similarity	NPD4689	Approved
0.5698	Remote Similarity	NPD4688	Approved
0.5698	Remote Similarity	NPD5205	Approved
0.5698	Remote Similarity	NPD4138	Approved
0.5667	Remote Similarity	NPD8171	Discontinued
0.5663	Remote Similarity	NPD6902	Approved
0.5647	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.561	Remote Similarity	NPD6683	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