NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.13
Volume:	264.021
LogP:	3.569
LogD:	3.17
LogS:	-2.947
# Rotatable Bonds:	0
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.685
Synthetic Accessibility Score:	4.098
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.835
MDCK Permeability:	1.952010097738821e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.15
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.941
30% Bioavailability (F30%):	0.424

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	96.1736831665039%
Volume Distribution (VD):	1.482
Pgp-substrate:	3.644057273864746%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.753
CYP2C19-inhibitor:	0.234
CYP2C19-substrate:	0.403
CYP2C9-inhibitor:	0.316
CYP2C9-substrate:	0.862
CYP2D6-inhibitor:	0.652
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.73
CYP3A4-substrate:	0.517

ADMET: Excretion

Clearance (CL):	11.262
Half-life (T1/2):	0.835

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.339
Drug-inuced Liver Injury (DILI):	0.061
AMES Toxicity:	0.476
Rat Oral Acute Toxicity:	0.731
Maximum Recommended Daily Dose:	0.716
Skin Sensitization:	0.666
Carcinogencity:	0.763
Eye Corrosion:	0.684
Eye Irritation:	0.793
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC87141

Natural Product ID:	NPC87141
*Common Name:**	Cordiachrome A
IUPAC Name:	(8aR,10aS)-8,10a-dimethyl-6,8a,9,10-tetrahydro-5H-anthracene-1,4-dione
Synonyms:
Standard InCHIKey:	GXIJLOWPICPBSR-BBRMVZONSA-N
Standard InCHI:	InChI=1S/C16H18O2/c1-10-4-3-7-16(2)9-12-11(8-13(10)16)14(17)5-6-15(12)18/h4-6,13H,3,7-9H2,1-2H3/t13-,16-/m0/s1
SMILES:	O=C1C=CC(=O)C2=C1C[C@]1(C)CCC=C([C@@H]1C2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL255103
PubChem CID:	44448148
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO6865	Cordia fragrantissima	Species	Cordiaceae	Eukaryota	n.a.	Myanmar	n.a.	PMID[18088097]
NPO6865	Cordia fragrantissima	Species	Cordiaceae	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	3

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1229	Cell Line	Huh-7	Homo sapiens	IC50	=	61.1	ug.mL-1	PMID[553969]
NPT841	Organism	Leishmania major	Leishmania major	IC50	=	4.1	ug.mL-1	PMID[553969]
NPT27	Others	Unspecified		IC50	=	22.5	ug.mL-1	PMID[553969]

☑ 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 NPC87141 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	238
0.1-0.2	2249
0.2-0.3	12831
0.3-0.4	14930
0.4-0.5	7616
0.5-0.6	3704
0.6-0.7	908
0.7-0.8	198
0.8-0.85	13
0.85-0.9	5
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9688	High Similarity	NPC260474
0.9688	High Similarity	NPC188292
0.9524	High Similarity	NPC251118
0.9242	High Similarity	NPC256846
0.9206	High Similarity	NPC288253
0.9091	High Similarity	NPC310992
0.8971	High Similarity	NPC54123
0.8841	High Similarity	NPC470045
0.8841	High Similarity	NPC470044
0.8824	High Similarity	NPC265782
0.8824	High Similarity	NPC251929
0.8824	High Similarity	NPC2634
0.8769	High Similarity	NPC469662
0.8732	High Similarity	NPC1254
0.8696	High Similarity	NPC181204
0.8696	High Similarity	NPC5701
0.8676	High Similarity	NPC139397
0.8615	High Similarity	NPC202118
0.8615	High Similarity	NPC197238
0.8594	High Similarity	NPC127582
0.8571	High Similarity	NPC251705
0.8571	High Similarity	NPC311852
0.8571	High Similarity	NPC303613
0.8571	High Similarity	NPC474228
0.8551	High Similarity	NPC260040
0.8551	High Similarity	NPC307176
0.8529	High Similarity	NPC155198
0.8485	Intermediate Similarity	NPC285371
0.8485	Intermediate Similarity	NPC212210
0.8485	Intermediate Similarity	NPC475124
0.8472	Intermediate Similarity	NPC69408
0.8451	Intermediate Similarity	NPC309852
0.8438	Intermediate Similarity	NPC472304
0.8438	Intermediate Similarity	NPC276764
0.8429	Intermediate Similarity	NPC305501
0.8429	Intermediate Similarity	NPC234707
0.8429	Intermediate Similarity	NPC225467
0.8429	Intermediate Similarity	NPC115023
0.8429	Intermediate Similarity	NPC190035
0.8333	Intermediate Similarity	NPC476346
0.8333	Intermediate Similarity	NPC473171
0.8333	Intermediate Similarity	NPC293803
0.8286	Intermediate Similarity	NPC159577
0.8286	Intermediate Similarity	NPC282593
0.8286	Intermediate Similarity	NPC35734
0.8281	Intermediate Similarity	NPC27610
0.8281	Intermediate Similarity	NPC56905
0.8243	Intermediate Similarity	NPC189485
0.8235	Intermediate Similarity	NPC323005
0.8209	Intermediate Similarity	NPC6697
0.8209	Intermediate Similarity	NPC4638
0.8194	Intermediate Similarity	NPC219232
0.8194	Intermediate Similarity	NPC255021
0.8194	Intermediate Similarity	NPC474796
0.8194	Intermediate Similarity	NPC474797
0.8194	Intermediate Similarity	NPC128346
0.8194	Intermediate Similarity	NPC329866
0.8182	Intermediate Similarity	NPC60565
0.8182	Intermediate Similarity	NPC213152
0.8169	Intermediate Similarity	NPC474562
0.8158	Intermediate Similarity	NPC475833
0.8143	Intermediate Similarity	NPC182815
0.8143	Intermediate Similarity	NPC286814
0.8133	Intermediate Similarity	NPC170793
0.8133	Intermediate Similarity	NPC27817
0.8133	Intermediate Similarity	NPC90965
0.8125	Intermediate Similarity	NPC115385
0.8116	Intermediate Similarity	NPC290350
0.8116	Intermediate Similarity	NPC4370
0.8116	Intermediate Similarity	NPC475523
0.8088	Intermediate Similarity	NPC470329
0.8082	Intermediate Similarity	NPC255650
0.806	Intermediate Similarity	NPC165695
0.8056	Intermediate Similarity	NPC56747
0.8056	Intermediate Similarity	NPC180015
0.8056	Intermediate Similarity	NPC130016
0.8056	Intermediate Similarity	NPC109576
0.8026	Intermediate Similarity	NPC474509
0.8026	Intermediate Similarity	NPC108955
0.8026	Intermediate Similarity	NPC476809
0.8	Intermediate Similarity	NPC296697
0.8	Intermediate Similarity	NPC74410
0.8	Intermediate Similarity	NPC60772
0.8	Intermediate Similarity	NPC170799
0.8	Intermediate Similarity	NPC20610
0.8	Intermediate Similarity	NPC82477
0.8	Intermediate Similarity	NPC142754
0.8	Intermediate Similarity	NPC308108
0.8	Intermediate Similarity	NPC115515
0.8	Intermediate Similarity	NPC39157
0.7973	Intermediate Similarity	NPC469793
0.7973	Intermediate Similarity	NPC469796
0.7971	Intermediate Similarity	NPC92327
0.7949	Intermediate Similarity	NPC49019
0.7945	Intermediate Similarity	NPC211641
0.7937	Intermediate Similarity	NPC5626
0.7922	Intermediate Similarity	NPC474085
0.7922	Intermediate Similarity	NPC116797
0.7922	Intermediate Similarity	NPC55869
0.7922	Intermediate Similarity	NPC99308
0.7917	Intermediate Similarity	NPC470078
0.7917	Intermediate Similarity	NPC223187
0.7879	Intermediate Similarity	NPC259261
0.7867	Intermediate Similarity	NPC472300
0.7857	Intermediate Similarity	NPC20181
0.7857	Intermediate Similarity	NPC176107
0.7857	Intermediate Similarity	NPC220210
0.7857	Intermediate Similarity	NPC193770
0.7838	Intermediate Similarity	NPC65650
0.7821	Intermediate Similarity	NPC142253
0.7821	Intermediate Similarity	NPC3511
0.7812	Intermediate Similarity	NPC200258
0.7808	Intermediate Similarity	NPC474488
0.7794	Intermediate Similarity	NPC32285
0.7792	Intermediate Similarity	NPC26139
0.7778	Intermediate Similarity	NPC40574
0.7778	Intermediate Similarity	NPC14002
0.7778	Intermediate Similarity	NPC246722
0.7778	Intermediate Similarity	NPC151045
0.7778	Intermediate Similarity	NPC23117
0.7778	Intermediate Similarity	NPC268564
0.7763	Intermediate Similarity	NPC275494
0.7763	Intermediate Similarity	NPC469996
0.7763	Intermediate Similarity	NPC471409
0.7761	Intermediate Similarity	NPC25853
0.775	Intermediate Similarity	NPC474537
0.7733	Intermediate Similarity	NPC180886
0.7733	Intermediate Similarity	NPC470525
0.7733	Intermediate Similarity	NPC110725
0.7727	Intermediate Similarity	NPC266295
0.7727	Intermediate Similarity	NPC30215
0.7727	Intermediate Similarity	NPC94991
0.7714	Intermediate Similarity	NPC176171
0.7703	Intermediate Similarity	NPC20025
0.7692	Intermediate Similarity	NPC225515
0.7692	Intermediate Similarity	NPC470034
0.7692	Intermediate Similarity	NPC278459
0.7671	Intermediate Similarity	NPC21944
0.7671	Intermediate Similarity	NPC133253
0.7662	Intermediate Similarity	NPC476177
0.7662	Intermediate Similarity	NPC472490
0.7647	Intermediate Similarity	NPC97322
0.7647	Intermediate Similarity	NPC475795
0.7632	Intermediate Similarity	NPC165711
0.7625	Intermediate Similarity	NPC87552
0.7612	Intermediate Similarity	NPC96551
0.7612	Intermediate Similarity	NPC285594
0.7595	Intermediate Similarity	NPC238991
0.7595	Intermediate Similarity	NPC472867
0.7595	Intermediate Similarity	NPC302661
0.7595	Intermediate Similarity	NPC472239
0.7595	Intermediate Similarity	NPC103486
0.7576	Intermediate Similarity	NPC192427
0.7564	Intermediate Similarity	NPC287063
0.7564	Intermediate Similarity	NPC472478
0.7564	Intermediate Similarity	NPC2482
0.7564	Intermediate Similarity	NPC469637
0.7561	Intermediate Similarity	NPC470523
0.7534	Intermediate Similarity	NPC214770
0.7534	Intermediate Similarity	NPC477856
0.7532	Intermediate Similarity	NPC470052
0.7532	Intermediate Similarity	NPC82635
0.7532	Intermediate Similarity	NPC478247
0.7532	Intermediate Similarity	NPC478246
0.7531	Intermediate Similarity	NPC33663
0.7531	Intermediate Similarity	NPC132228
0.7531	Intermediate Similarity	NPC263997
0.7531	Intermediate Similarity	NPC8518
0.7531	Intermediate Similarity	NPC133652
0.7531	Intermediate Similarity	NPC29447
0.7531	Intermediate Similarity	NPC476426
0.7531	Intermediate Similarity	NPC8571
0.75	Intermediate Similarity	NPC41539
0.75	Intermediate Similarity	NPC19907
0.75	Intermediate Similarity	NPC474463
0.75	Intermediate Similarity	NPC40353
0.75	Intermediate Similarity	NPC53733
0.75	Intermediate Similarity	NPC118423
0.75	Intermediate Similarity	NPC92080
0.747	Intermediate Similarity	NPC470524
0.7468	Intermediate Similarity	NPC473217
0.7468	Intermediate Similarity	NPC121984
0.7468	Intermediate Similarity	NPC475863
0.7468	Intermediate Similarity	NPC149237
0.7468	Intermediate Similarity	NPC471898
0.7467	Intermediate Similarity	NPC476046
0.7467	Intermediate Similarity	NPC241854
0.7467	Intermediate Similarity	NPC251970
0.746	Intermediate Similarity	NPC64866
0.7439	Intermediate Similarity	NPC222613
0.7439	Intermediate Similarity	NPC475022
0.7439	Intermediate Similarity	NPC118648
0.7436	Intermediate Similarity	NPC19900
0.7432	Intermediate Similarity	NPC304983
0.7429	Intermediate Similarity	NPC473902
0.7429	Intermediate Similarity	NPC169275
0.7429	Intermediate Similarity	NPC52449
0.7424	Intermediate Similarity	NPC473733
0.7407	Intermediate Similarity	NPC473246
0.7403	Intermediate Similarity	NPC91665

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 NPC87141 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	2525
0.2-0.3	4342
0.3-0.4	1454
0.4-0.5	358
0.5-0.6	167
0.6-0.7	60
0.7-0.8	10
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD4691	Approved
0.8714	High Similarity	NPD4058	Approved
0.8714	High Similarity	NPD4687	Approved
0.8676	High Similarity	NPD4137	Phase 3
0.8551	High Similarity	NPD4747	Approved
0.8451	Intermediate Similarity	NPD5733	Approved
0.8429	Intermediate Similarity	NPD5276	Approved
0.8	Intermediate Similarity	NPD287	Approved
0.8	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8028	Phase 2
0.7654	Intermediate Similarity	NPD5690	Phase 2
0.7564	Intermediate Similarity	NPD4695	Discontinued
0.7375	Intermediate Similarity	NPD4223	Phase 3
0.7375	Intermediate Similarity	NPD4221	Approved
0.7349	Intermediate Similarity	NPD3573	Approved
0.7229	Intermediate Similarity	NPD4519	Discontinued
0.7229	Intermediate Similarity	NPD5280	Approved
0.7229	Intermediate Similarity	NPD4694	Approved
0.7229	Intermediate Similarity	NPD4623	Approved
0.7195	Intermediate Similarity	NPD3665	Phase 1
0.7195	Intermediate Similarity	NPD4197	Approved
0.7195	Intermediate Similarity	NPD3133	Approved
0.7195	Intermediate Similarity	NPD3666	Approved
0.7108	Intermediate Similarity	NPD5329	Approved
0.7093	Intermediate Similarity	NPD5207	Approved
0.7089	Intermediate Similarity	NPD3617	Approved
0.7059	Intermediate Similarity	NPD4518	Approved
0.7024	Intermediate Similarity	NPD5205	Approved
0.7024	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4688	Approved
0.7024	Intermediate Similarity	NPD7521	Approved
0.7024	Intermediate Similarity	NPD7334	Approved
0.7024	Intermediate Similarity	NPD6409	Approved
0.7024	Intermediate Similarity	NPD5330	Approved
0.7024	Intermediate Similarity	NPD7146	Approved
0.7024	Intermediate Similarity	NPD4689	Approved
0.7024	Intermediate Similarity	NPD3618	Phase 1
0.7024	Intermediate Similarity	NPD4138	Approved
0.7024	Intermediate Similarity	NPD6684	Approved
0.7024	Intermediate Similarity	NPD4693	Phase 3
0.7024	Intermediate Similarity	NPD4690	Approved
0.7024	Intermediate Similarity	NPD5279	Phase 3
0.7011	Intermediate Similarity	NPD5284	Approved
0.7011	Intermediate Similarity	NPD5281	Approved
0.7011	Intermediate Similarity	NPD6079	Approved
0.7011	Intermediate Similarity	NPD5694	Approved
0.7	Intermediate Similarity	NPD4195	Approved
0.6951	Remote Similarity	NPD3667	Approved
0.6897	Remote Similarity	NPD5692	Phase 3
0.686	Remote Similarity	NPD6672	Approved
0.686	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5737	Approved
0.686	Remote Similarity	NPD5208	Approved
0.686	Remote Similarity	NPD6903	Approved
0.6818	Remote Similarity	NPD6050	Approved
0.6786	Remote Similarity	NPD4786	Approved
0.6786	Remote Similarity	NPD3668	Phase 3
0.6782	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5328	Approved
0.6782	Remote Similarity	NPD4753	Phase 2
0.6782	Remote Similarity	NPD6673	Approved
0.6782	Remote Similarity	NPD6080	Approved
0.6782	Remote Similarity	NPD6904	Approved
0.6778	Remote Similarity	NPD4629	Approved
0.6778	Remote Similarity	NPD5210	Approved
0.6757	Remote Similarity	NPD7331	Phase 2
0.6707	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4096	Approved
0.6703	Remote Similarity	NPD5222	Approved
0.6703	Remote Similarity	NPD5221	Approved
0.6703	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3495	Discontinued
0.663	Remote Similarity	NPD5173	Approved
0.6629	Remote Similarity	NPD7515	Phase 2
0.6629	Remote Similarity	NPD5693	Phase 1
0.6628	Remote Similarity	NPD6098	Approved
0.6627	Remote Similarity	NPD4692	Approved
0.6627	Remote Similarity	NPD4139	Approved
0.6593	Remote Similarity	NPD5695	Phase 3
0.6556	Remote Similarity	NPD5133	Approved
0.6556	Remote Similarity	NPD4202	Approved
0.6548	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7732	Phase 3
0.6522	Remote Similarity	NPD7614	Phase 1
0.6512	Remote Similarity	NPD1694	Approved
0.6489	Remote Similarity	NPD4696	Approved
0.6489	Remote Similarity	NPD5285	Approved
0.6489	Remote Similarity	NPD5286	Approved
0.6484	Remote Similarity	NPD7748	Approved
0.6484	Remote Similarity	NPD7900	Approved
0.6484	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6001	Approved
0.6438	Remote Similarity	NPD4191	Approved
0.6438	Remote Similarity	NPD4192	Approved
0.6438	Remote Similarity	NPD4194	Approved
0.6438	Remote Similarity	NPD4193	Approved
0.6421	Remote Similarity	NPD5223	Approved
0.6413	Remote Similarity	NPD5654	Approved
0.6413	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7341	Phase 2
0.6374	Remote Similarity	NPD7631	Approved
0.6354	Remote Similarity	NPD5224	Approved
0.6354	Remote Similarity	NPD5091	Approved
0.6354	Remote Similarity	NPD5211	Phase 2
0.6354	Remote Similarity	NPD5226	Approved
0.6354	Remote Similarity	NPD5225	Approved
0.6354	Remote Similarity	NPD4633	Approved
0.6344	Remote Similarity	NPD4697	Phase 3
0.6316	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5174	Approved
0.6289	Remote Similarity	NPD5175	Approved
0.6279	Remote Similarity	NPD4788	Approved
0.6277	Remote Similarity	NPD6084	Phase 2
0.6277	Remote Similarity	NPD4755	Approved
0.6277	Remote Similarity	NPD6083	Phase 2
0.6277	Remote Similarity	NPD5959	Approved
0.6277	Remote Similarity	NPD7902	Approved
0.6264	Remote Similarity	NPD7609	Phase 3
0.6224	Remote Similarity	NPD5141	Approved
0.6211	Remote Similarity	NPD5696	Approved
0.6196	Remote Similarity	NPD6399	Phase 3
0.6146	Remote Similarity	NPD4700	Approved
0.6146	Remote Similarity	NPD6404	Discontinued
0.6133	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD8262	Approved
0.61	Remote Similarity	NPD6614	Approved
0.61	Remote Similarity	NPD5697	Approved
0.6098	Remote Similarity	NPD8039	Approved
0.6087	Remote Similarity	NPD6411	Approved
0.6061	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4729	Approved
0.604	Remote Similarity	NPD5168	Approved
0.604	Remote Similarity	NPD6881	Approved
0.604	Remote Similarity	NPD4730	Approved
0.604	Remote Similarity	NPD6011	Approved
0.604	Remote Similarity	NPD6899	Approved
0.6	Remote Similarity	NPD650	Approved
0.598	Remote Similarity	NPD6012	Approved
0.598	Remote Similarity	NPD6014	Approved
0.598	Remote Similarity	NPD6013	Approved
0.5976	Remote Similarity	NPD4784	Approved
0.5976	Remote Similarity	NPD4785	Approved
0.596	Remote Similarity	NPD4754	Approved
0.596	Remote Similarity	NPD6052	Approved
0.5955	Remote Similarity	NPD1696	Phase 3
0.5938	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD4243	Approved
0.5922	Remote Similarity	NPD5169	Approved
0.5922	Remote Similarity	NPD5248	Approved
0.5922	Remote Similarity	NPD5247	Approved
0.5922	Remote Similarity	NPD7290	Approved
0.5922	Remote Similarity	NPD5249	Phase 3
0.5922	Remote Similarity	NPD4634	Approved
0.5922	Remote Similarity	NPD6883	Approved
0.5922	Remote Similarity	NPD7102	Approved
0.5922	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5250	Approved
0.5922	Remote Similarity	NPD5135	Approved
0.5922	Remote Similarity	NPD5251	Approved
0.5904	Remote Similarity	NPD8264	Approved
0.5882	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5128	Approved
0.587	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.587	Remote Similarity	NPD6101	Approved
0.5865	Remote Similarity	NPD8130	Phase 1
0.5865	Remote Similarity	NPD6650	Approved
0.5865	Remote Similarity	NPD5217	Approved
0.5865	Remote Similarity	NPD5127	Approved
0.5865	Remote Similarity	NPD5215	Approved
0.5865	Remote Similarity	NPD5216	Approved
0.5865	Remote Similarity	NPD6847	Approved
0.5865	Remote Similarity	NPD6617	Approved
0.5865	Remote Similarity	NPD6649	Approved
0.5865	Remote Similarity	NPD6869	Approved
0.5844	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD6402	Approved
0.5842	Remote Similarity	NPD5739	Approved
0.5842	Remote Similarity	NPD6008	Approved
0.5842	Remote Similarity	NPD4768	Approved
0.5842	Remote Similarity	NPD7128	Approved
0.5842	Remote Similarity	NPD6675	Approved
0.5842	Remote Similarity	NPD4767	Approved
0.5833	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6882	Approved
0.581	Remote Similarity	NPD8297	Approved
0.5795	Remote Similarity	NPD5209	Approved
0.5789	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD6412	Phase 2
0.5784	Remote Similarity	NPD5701	Approved
0.5755	Remote Similarity	NPD4632	Approved
0.5753	Remote Similarity	NPD4219	Approved
0.5728	Remote Similarity	NPD7320	Approved
0.5714	Remote Similarity	NPD5275	Approved
0.5714	Remote Similarity	NPD7339	Approved
0.5714	Remote Similarity	NPD5290	Discontinued
0.5714	Remote Similarity	NPD4190	Phase 3
0.5714	Remote Similarity	NPD6942	Approved
0.5701	Remote Similarity	NPD5167	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