NPASS Compound

Structure

NPC237510 OpenBabel07101718322D 24 26 0 0 1 0 0 0 0 0999 V2000 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 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 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 1.7321 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 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 -0.8660 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 13 20 1 1 0 0 0 14 16 1 0 0 0 0 14 23 1 1 0 0 0 15 18 1 1 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 20 1 6 0 0 0 17 18 1 1 0 0 0 17 19 1 0 0 0 0 18 3 1 1 0 0 0 19 4 1 6 0 0 0 19 24 1 0 0 0 0 20 11 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.09
Volume:	384.954
LogP:	5.152
LogD:	4.295
LogS:	-5.333
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.554
Synthetic Accessibility Score:	5.143
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.503
MDCK Permeability:	1.7921529433806427e-05
Pgp-inhibitor:	0.71
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.063
30% Bioavailability (F30%):	0.928

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.575
Plasma Protein Binding (PPB):	93.81798553466797%
Volume Distribution (VD):	1.155
Pgp-substrate:	5.0601630210876465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.246
CYP1A2-substrate:	0.369
CYP2C19-inhibitor:	0.135
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.568
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.199
CYP3A4-inhibitor:	0.731
CYP3A4-substrate:	0.505

ADMET: Excretion

Clearance (CL):	9.379
Half-life (T1/2):	0.056

ADMET: Toxicity

hERG Blockers:	0.22
Human Hepatotoxicity (H-HT):	0.257
Drug-inuced Liver Injury (DILI):	0.841
AMES Toxicity:	0.127
Rat Oral Acute Toxicity:	0.62
Maximum Recommended Daily Dose:	0.046
Skin Sensitization:	0.913
Carcinogencity:	0.773
Eye Corrosion:	0.98
Eye Irritation:	0.228
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC237510

Natural Product ID:	NPC237510
*Common Name:**	1S-Hydroxy-1,2-Dihydro-Bromosphaerol
IUPAC Name:	(1S,4S,4aS,4bS,5R,8S,8aS,10aS)-8-bromo-10a-(bromomethyl)-5,8a-dimethyl-1-propan-2-yl-2,3,4,4a,4b,6,7,8,9,10-decahydro-1H-phenanthrene-4,5-diol
Synonyms:
Standard InCHIKey:	OBFXRJSCWYURMT-KKVUZGIASA-N
Standard InCHI:	InChI=1S/C20H34Br2O2/c1-12(2)13-5-6-14(23)16-17-18(3,9-10-20(13,16)11-21)15(22)7-8-19(17,4)24/h12-17,23-24H,5-11H2,1-4H3/t13-,14-,15-,16-,17-,18+,19+,20-/m0/s1
SMILES:	BrC[C@@]12CC[C@]3([C@H]([C@@H]2[C@H](CC[C@H]1C(C)C)O)[C@](C)(O)CC[C@@H]3Br)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL598468
PubChem CID:	25033524
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO29354	Sphaerococcus coronopifolius	Species	Sphaerococcaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520219]
NPO29354	Sphaerococcus coronopifolius	Species	Sphaerococcaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18597527]
NPO29354	Sphaerococcus coronopifolius	Species	Sphaerococcaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20045651]
NPO29354	Sphaerococcus coronopifolius	Species	Sphaerococcaceae	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	6

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	28600.0	nM	PMID[489391]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	26000.0	nM	PMID[489391]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	25000.0	nM	PMID[489391]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	23000.0	nM	PMID[489391]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	25000.0	nM	PMID[489391]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	20000.0	nM	PMID[489391]

☑ 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 NPC237510 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	486
0.1-0.2	5706
0.2-0.3	19414
0.3-0.4	7790
0.4-0.5	5535
0.5-0.6	3009
0.6-0.7	657
0.7-0.8	96
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475793
0.8553	High Similarity	NPC329871
0.85	High Similarity	NPC475276
0.8375	Intermediate Similarity	NPC313115
0.8	Intermediate Similarity	NPC476422
0.7857	Intermediate Similarity	NPC131453
0.7794	Intermediate Similarity	NPC236588
0.7794	Intermediate Similarity	NPC135438
0.7778	Intermediate Similarity	NPC80463
0.7778	Intermediate Similarity	NPC260116
0.7765	Intermediate Similarity	NPC224552
0.7765	Intermediate Similarity	NPC239453
0.7703	Intermediate Similarity	NPC472741
0.7671	Intermediate Similarity	NPC44122
0.7647	Intermediate Similarity	NPC475817
0.7647	Intermediate Similarity	NPC188896
0.76	Intermediate Similarity	NPC66407
0.76	Intermediate Similarity	NPC470833
0.7568	Intermediate Similarity	NPC48079
0.7564	Intermediate Similarity	NPC476424
0.75	Intermediate Similarity	NPC292419
0.75	Intermediate Similarity	NPC282454
0.75	Intermediate Similarity	NPC114891
0.75	Intermediate Similarity	NPC290791
0.747	Intermediate Similarity	NPC163616
0.7467	Intermediate Similarity	NPC475893
0.7444	Intermediate Similarity	NPC156912
0.7432	Intermediate Similarity	NPC142712
0.7407	Intermediate Similarity	NPC129501
0.7403	Intermediate Similarity	NPC157422
0.7403	Intermediate Similarity	NPC1340
0.7403	Intermediate Similarity	NPC470071
0.7403	Intermediate Similarity	NPC127094
0.7403	Intermediate Similarity	NPC109457
0.7403	Intermediate Similarity	NPC100586
0.7403	Intermediate Similarity	NPC187471
0.7403	Intermediate Similarity	NPC252182
0.7397	Intermediate Similarity	NPC118937
0.7397	Intermediate Similarity	NPC159654
0.7397	Intermediate Similarity	NPC167995
0.7397	Intermediate Similarity	NPC281540
0.7368	Intermediate Similarity	NPC241085
0.7368	Intermediate Similarity	NPC254037
0.7368	Intermediate Similarity	NPC299948
0.7368	Intermediate Similarity	NPC477820
0.7368	Intermediate Similarity	NPC470830
0.7368	Intermediate Similarity	NPC210323
0.7368	Intermediate Similarity	NPC129829
0.7368	Intermediate Similarity	NPC107919
0.7363	Intermediate Similarity	NPC34732
0.7363	Intermediate Similarity	NPC92231
0.7361	Intermediate Similarity	NPC218585
0.7361	Intermediate Similarity	NPC148174
0.7361	Intermediate Similarity	NPC71460
0.7333	Intermediate Similarity	NPC299714
0.7333	Intermediate Similarity	NPC473230
0.7333	Intermediate Similarity	NPC204233
0.7333	Intermediate Similarity	NPC475884
0.7333	Intermediate Similarity	NPC257510
0.7308	Intermediate Similarity	NPC253805
0.7297	Intermediate Similarity	NPC474380
0.7297	Intermediate Similarity	NPC41577
0.7297	Intermediate Similarity	NPC473276
0.7273	Intermediate Similarity	NPC232925
0.7273	Intermediate Similarity	NPC63588
0.7273	Intermediate Similarity	NPC251201
0.7273	Intermediate Similarity	NPC231945
0.7273	Intermediate Similarity	NPC192192
0.7246	Intermediate Similarity	NPC471269
0.7237	Intermediate Similarity	NPC469987
0.7237	Intermediate Similarity	NPC2648
0.7215	Intermediate Similarity	NPC192501
0.7215	Intermediate Similarity	NPC10476
0.7215	Intermediate Similarity	NPC228994
0.7215	Intermediate Similarity	NPC304499
0.7179	Intermediate Similarity	NPC478103
0.7179	Intermediate Similarity	NPC195530
0.7179	Intermediate Similarity	NPC473279
0.7162	Intermediate Similarity	NPC69149
0.7125	Intermediate Similarity	NPC317242
0.7125	Intermediate Similarity	NPC158208
0.7125	Intermediate Similarity	NPC3403
0.7125	Intermediate Similarity	NPC243027
0.7125	Intermediate Similarity	NPC196136
0.7105	Intermediate Similarity	NPC476928
0.7105	Intermediate Similarity	NPC63190
0.7089	Intermediate Similarity	NPC473238
0.7089	Intermediate Similarity	NPC472341
0.7089	Intermediate Similarity	NPC153719
0.7089	Intermediate Similarity	NPC470610
0.7037	Intermediate Similarity	NPC163597
0.7	Intermediate Similarity	NPC477508
0.7	Intermediate Similarity	NPC48795
0.6962	Remote Similarity	NPC131506
0.6962	Remote Similarity	NPC157777
0.6951	Remote Similarity	NPC192046
0.6951	Remote Similarity	NPC476233
0.6951	Remote Similarity	NPC185915
0.6951	Remote Similarity	NPC475031
0.6951	Remote Similarity	NPC477227
0.6951	Remote Similarity	NPC474574
0.6951	Remote Similarity	NPC64081
0.6951	Remote Similarity	NPC105208
0.6951	Remote Similarity	NPC128951
0.6951	Remote Similarity	NPC302578
0.6944	Remote Similarity	NPC476735
0.6944	Remote Similarity	NPC47663
0.6932	Remote Similarity	NPC174273
0.6914	Remote Similarity	NPC91387
0.6914	Remote Similarity	NPC270306
0.6914	Remote Similarity	NPC231680
0.6883	Remote Similarity	NPC139207
0.6883	Remote Similarity	NPC185874
0.6875	Remote Similarity	NPC477229
0.6875	Remote Similarity	NPC211009
0.6875	Remote Similarity	NPC81759
0.6875	Remote Similarity	NPC476609
0.6875	Remote Similarity	NPC68426
0.6875	Remote Similarity	NPC232112
0.6875	Remote Similarity	NPC282905
0.6867	Remote Similarity	NPC147993
0.6867	Remote Similarity	NPC67657
0.6867	Remote Similarity	NPC18857
0.6867	Remote Similarity	NPC301707
0.6867	Remote Similarity	NPC471769
0.6857	Remote Similarity	NPC53209
0.6842	Remote Similarity	NPC190827
0.6842	Remote Similarity	NPC475943
0.6842	Remote Similarity	NPC243469
0.6842	Remote Similarity	NPC472946
0.6835	Remote Similarity	NPC45296
0.6829	Remote Similarity	NPC91573
0.6829	Remote Similarity	NPC470145
0.6829	Remote Similarity	NPC14112
0.6829	Remote Similarity	NPC86305
0.6795	Remote Similarity	NPC474756
0.679	Remote Similarity	NPC308440
0.679	Remote Similarity	NPC472503
0.679	Remote Similarity	NPC168511
0.679	Remote Similarity	NPC478130
0.679	Remote Similarity	NPC159325
0.679	Remote Similarity	NPC74639
0.6786	Remote Similarity	NPC477282
0.6786	Remote Similarity	NPC80530
0.6786	Remote Similarity	NPC273410
0.6786	Remote Similarity	NPC287452
0.6786	Remote Similarity	NPC81074
0.675	Remote Similarity	NPC89310
0.675	Remote Similarity	NPC320549
0.675	Remote Similarity	NPC127283
0.675	Remote Similarity	NPC301226
0.675	Remote Similarity	NPC151018
0.675	Remote Similarity	NPC167706
0.675	Remote Similarity	NPC111234
0.675	Remote Similarity	NPC8004
0.675	Remote Similarity	NPC58057
0.675	Remote Similarity	NPC475077
0.675	Remote Similarity	NPC156277
0.6747	Remote Similarity	NPC23884
0.6747	Remote Similarity	NPC470758
0.6747	Remote Similarity	NPC169994
0.6747	Remote Similarity	NPC133596
0.6747	Remote Similarity	NPC11907
0.6747	Remote Similarity	NPC138502
0.6747	Remote Similarity	NPC207010
0.6747	Remote Similarity	NPC317913
0.6747	Remote Similarity	NPC470711
0.6714	Remote Similarity	NPC102336
0.6714	Remote Similarity	NPC36002
0.6712	Remote Similarity	NPC87296
0.6712	Remote Similarity	NPC475515
0.6712	Remote Similarity	NPC215671
0.6711	Remote Similarity	NPC94897
0.6711	Remote Similarity	NPC101128
0.6709	Remote Similarity	NPC6120
0.6709	Remote Similarity	NPC99264
0.6709	Remote Similarity	NPC131892
0.6709	Remote Similarity	NPC327728
0.6709	Remote Similarity	NPC213178
0.6707	Remote Similarity	NPC70982
0.6707	Remote Similarity	NPC195155
0.6707	Remote Similarity	NPC178383
0.6707	Remote Similarity	NPC472950
0.6707	Remote Similarity	NPC212733
0.6707	Remote Similarity	NPC144075
0.6707	Remote Similarity	NPC472952
0.6707	Remote Similarity	NPC273366
0.6707	Remote Similarity	NPC231256
0.6707	Remote Similarity	NPC476605
0.6707	Remote Similarity	NPC267753
0.6707	Remote Similarity	NPC212879
0.6707	Remote Similarity	NPC185536
0.6707	Remote Similarity	NPC104387
0.6707	Remote Similarity	NPC240235
0.6707	Remote Similarity	NPC230704
0.6707	Remote Similarity	NPC97534
0.6707	Remote Similarity	NPC174964
0.6706	Remote Similarity	NPC16449
0.6706	Remote Similarity	NPC322313
0.6706	Remote Similarity	NPC236237

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 NPC237510 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	617
0.1-0.2	4868
0.2-0.3	2747
0.3-0.4	553
0.4-0.5	250
0.5-0.6	87
0.6-0.7	26
0.7-0.8	2
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
0.7368	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3671	Phase 1
0.7051	Intermediate Similarity	NPD4787	Phase 1
0.675	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6116	Phase 1
0.6709	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7525	Registered
0.6627	Remote Similarity	NPD6117	Approved
0.6585	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD3703	Phase 2
0.6471	Remote Similarity	NPD6114	Approved
0.6471	Remote Similarity	NPD6115	Approved
0.6471	Remote Similarity	NPD6118	Approved
0.6471	Remote Similarity	NPD6697	Approved
0.642	Remote Similarity	NPD4244	Approved
0.642	Remote Similarity	NPD4245	Approved
0.6395	Remote Similarity	NPD7645	Phase 2
0.6375	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD5360	Phase 3
0.6324	Remote Similarity	NPD385	Approved
0.6324	Remote Similarity	NPD384	Approved
0.6322	Remote Similarity	NPD6928	Phase 2
0.6296	Remote Similarity	NPD3698	Phase 2
0.622	Remote Similarity	NPD4789	Approved
0.6076	Remote Similarity	NPD371	Approved
0.6	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD4758	Discontinued
0.593	Remote Similarity	NPD7339	Approved
0.593	Remote Similarity	NPD6942	Approved
0.5882	Remote Similarity	NPD7632	Discontinued
0.5862	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD6705	Phase 1
0.5778	Remote Similarity	NPD4748	Discontinued
0.5732	Remote Similarity	NPD4224	Phase 2
0.573	Remote Similarity	NPD5364	Discontinued
0.5714	Remote Similarity	NPD386	Approved
0.5714	Remote Similarity	NPD388	Approved
0.567	Remote Similarity	NPD6700	Approved
0.567	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD1810	Approved
0.5632	Remote Similarity	NPD6926	Approved
0.5632	Remote Similarity	NPD1811	Approved
0.5632	Remote Similarity	NPD6924	Approved
0.5612	Remote Similarity	NPD8034	Phase 2
0.5612	Remote Similarity	NPD7515	Phase 2
0.5612	Remote Similarity	NPD6703	Approved
0.5612	Remote Similarity	NPD8035	Phase 2
0.5612	Remote Similarity	NPD6702	Approved
0.5604	Remote Similarity	NPD7509	Discontinued

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