NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.13
Volume:	269.941
LogP:	3.111
LogD:	3.176
LogS:	-2.627
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.585
Synthetic Accessibility Score:	4.41
Fsp3:	0.25
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:	-4.814
MDCK Permeability:	1.8847418687073514e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.265
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.85
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	96.70541381835938%
Volume Distribution (VD):	0.723
Pgp-substrate:	2.9662468433380127%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.484
CYP2C19-inhibitor:	0.159
CYP2C19-substrate:	0.263
CYP2C9-inhibitor:	0.332
CYP2C9-substrate:	0.89
CYP2D6-inhibitor:	0.533
CYP2D6-substrate:	0.037
CYP3A4-inhibitor:	0.62
CYP3A4-substrate:	0.615

ADMET: Excretion

Clearance (CL):	8.316
Half-life (T1/2):	0.857

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.209
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.442
Maximum Recommended Daily Dose:	0.802
Skin Sensitization:	0.684
Carcinogencity:	0.827
Eye Corrosion:	0.922
Eye Irritation:	0.913
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: NPC251118

Natural Product ID:	NPC251118
*Common Name:**	Cordiachrome C
IUPAC Name:	(6S,7R)-7-ethenyl-7-methyl-6-prop-1-en-2-yl-6,8-dihydro-5H-naphthalene-1,4-dione
Synonyms:	Cordiachrome C
Standard InCHIKey:	KZWBZRSKUWXBGO-BBRMVZONSA-N
Standard InCHI:	InChI=1S/C16H18O2/c1-5-16(4)9-12-11(8-13(16)10(2)3)14(17)6-7-15(12)18/h5-7,13H,1-2,8-9H2,3-4H3/t13-,16-/m0/s1
SMILES:	C=C[C@@]1(C)CC2=C(C[C@H]1C(=C)C)C(=O)C=CC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL401583
PubChem CID:	44448135
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones

*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]
NPO22854	Cordia globifera	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19368377]
NPO22854	Cordia globifera	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384317]
NPO6865	Cordia fragrantissima	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22854	Cordia globifera	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	9
MIC	1

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	1.4	ug.mL-1	PMID[468733]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1.5	ug.mL-1	PMID[468733]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	0.2	ug.mL-1	PMID[468733]
NPT841	Organism	Leishmania major	Leishmania major	IC50	=	21.1	ug.mL-1	PMID[468732]
NPT3631	Organism	Leishmania guyanensis	Leishmania guyanensis	IC50	=	6.0	ug.mL-1	PMID[468732]
NPT3632	Organism	Leishmania panamensis	Leishmania panamensis	IC50	=	5.5	ug.mL-1	PMID[468732]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	1.5	ug.mL-1	PMID[468733]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.2	ug.mL-1	PMID[468733]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	4.6	ug.mL-1	PMID[468733]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.8	ug.mL-1	PMID[468733]

☑ 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 NPC251118 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	235
0.1-0.2	2274
0.2-0.3	13136
0.3-0.4	14421
0.4-0.5	7587
0.5-0.6	3787
0.6-0.7	988
0.7-0.8	223
0.8-0.85	34
0.85-0.9	7
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC87141
0.9524	High Similarity	NPC188292
0.9524	High Similarity	NPC260474
0.9375	High Similarity	NPC256846
0.9344	High Similarity	NPC288253
0.8923	High Similarity	NPC310992
0.8806	High Similarity	NPC5701
0.8806	High Similarity	NPC54123
0.871	High Similarity	NPC127582
0.8689	High Similarity	NPC311852
0.8676	High Similarity	NPC470045
0.8676	High Similarity	NPC470044
0.8657	High Similarity	NPC2634
0.8657	High Similarity	NPC265782
0.8657	High Similarity	NPC251929
0.8636	High Similarity	NPC155198
0.8594	High Similarity	NPC469662
0.8594	High Similarity	NPC285371
0.8594	High Similarity	NPC212210
0.8594	High Similarity	NPC475124
0.8571	High Similarity	NPC1254
0.8548	High Similarity	NPC472304
0.8548	High Similarity	NPC276764
0.8525	High Similarity	NPC115385
0.8507	High Similarity	NPC139397
0.8462	Intermediate Similarity	NPC470329
0.8438	Intermediate Similarity	NPC202118
0.8438	Intermediate Similarity	NPC197238
0.8438	Intermediate Similarity	NPC165695
0.8429	Intermediate Similarity	NPC476346
0.8406	Intermediate Similarity	NPC251705
0.8406	Intermediate Similarity	NPC303613
0.8406	Intermediate Similarity	NPC474228
0.8387	Intermediate Similarity	NPC27610
0.8387	Intermediate Similarity	NPC56905
0.8382	Intermediate Similarity	NPC260040
0.8382	Intermediate Similarity	NPC307176
0.831	Intermediate Similarity	NPC69408
0.8308	Intermediate Similarity	NPC4638
0.8308	Intermediate Similarity	NPC6697
0.8286	Intermediate Similarity	NPC474797
0.8286	Intermediate Similarity	NPC329866
0.8286	Intermediate Similarity	NPC309852
0.8286	Intermediate Similarity	NPC474796
0.8281	Intermediate Similarity	NPC60565
0.8281	Intermediate Similarity	NPC213152
0.8261	Intermediate Similarity	NPC225467
0.8261	Intermediate Similarity	NPC115023
0.8261	Intermediate Similarity	NPC181204
0.8261	Intermediate Similarity	NPC234707
0.8261	Intermediate Similarity	NPC190035
0.8261	Intermediate Similarity	NPC305501
0.8261	Intermediate Similarity	NPC474562
0.8254	Intermediate Similarity	NPC259261
0.8209	Intermediate Similarity	NPC290350
0.8209	Intermediate Similarity	NPC475523
0.8209	Intermediate Similarity	NPC4370
0.8169	Intermediate Similarity	NPC293803
0.8169	Intermediate Similarity	NPC473171
0.8167	Intermediate Similarity	NPC268564
0.8154	Intermediate Similarity	NPC32285
0.8143	Intermediate Similarity	NPC56747
0.8143	Intermediate Similarity	NPC109576
0.8143	Intermediate Similarity	NPC180015
0.8143	Intermediate Similarity	NPC130016
0.8125	Intermediate Similarity	NPC25853
0.8116	Intermediate Similarity	NPC35734
0.8116	Intermediate Similarity	NPC159577
0.8116	Intermediate Similarity	NPC282593
0.8095	Intermediate Similarity	NPC94991
0.8095	Intermediate Similarity	NPC30215
0.8095	Intermediate Similarity	NPC170799
0.8095	Intermediate Similarity	NPC308108
0.8095	Intermediate Similarity	NPC266295
0.8095	Intermediate Similarity	NPC60772
0.8082	Intermediate Similarity	NPC189485
0.8082	Intermediate Similarity	NPC74410
0.806	Intermediate Similarity	NPC323005
0.8056	Intermediate Similarity	NPC469796
0.8056	Intermediate Similarity	NPC469793
0.8033	Intermediate Similarity	NPC5626
0.8028	Intermediate Similarity	NPC128346
0.8028	Intermediate Similarity	NPC255021
0.8028	Intermediate Similarity	NPC219232
0.8	Intermediate Similarity	NPC97322
0.8	Intermediate Similarity	NPC475833
0.8	Intermediate Similarity	NPC475795
0.7973	Intermediate Similarity	NPC170793
0.7973	Intermediate Similarity	NPC90965
0.7973	Intermediate Similarity	NPC27817
0.7971	Intermediate Similarity	NPC286814
0.7971	Intermediate Similarity	NPC182815
0.7969	Intermediate Similarity	NPC285594
0.7969	Intermediate Similarity	NPC96551
0.7917	Intermediate Similarity	NPC65650
0.7917	Intermediate Similarity	NPC255650
0.7903	Intermediate Similarity	NPC200258
0.7869	Intermediate Similarity	NPC23117
0.7869	Intermediate Similarity	NPC14002
0.7867	Intermediate Similarity	NPC476809
0.7867	Intermediate Similarity	NPC108955
0.7867	Intermediate Similarity	NPC474509
0.7857	Intermediate Similarity	NPC151045
0.7857	Intermediate Similarity	NPC246722
0.7838	Intermediate Similarity	NPC275494
0.7838	Intermediate Similarity	NPC115515
0.7838	Intermediate Similarity	NPC471409
0.7838	Intermediate Similarity	NPC478246
0.7838	Intermediate Similarity	NPC478247
0.7833	Intermediate Similarity	NPC64866
0.7826	Intermediate Similarity	NPC39157
0.7826	Intermediate Similarity	NPC142754
0.7826	Intermediate Similarity	NPC82477
0.7826	Intermediate Similarity	NPC296697
0.7826	Intermediate Similarity	NPC20610
0.7808	Intermediate Similarity	NPC110725
0.7808	Intermediate Similarity	NPC470525
0.7808	Intermediate Similarity	NPC180886
0.7808	Intermediate Similarity	NPC40353
0.7794	Intermediate Similarity	NPC176171
0.7794	Intermediate Similarity	NPC92327
0.7778	Intermediate Similarity	NPC20025
0.7778	Intermediate Similarity	NPC211641
0.7778	Intermediate Similarity	NPC473733
0.7763	Intermediate Similarity	NPC99308
0.7763	Intermediate Similarity	NPC474085
0.7763	Intermediate Similarity	NPC55869
0.7763	Intermediate Similarity	NPC116797
0.7761	Intermediate Similarity	NPC473902
0.7746	Intermediate Similarity	NPC223187
0.7746	Intermediate Similarity	NPC470078
0.7746	Intermediate Similarity	NPC21944
0.7746	Intermediate Similarity	NPC133253
0.7714	Intermediate Similarity	NPC474060
0.7703	Intermediate Similarity	NPC472300
0.7681	Intermediate Similarity	NPC176107
0.7681	Intermediate Similarity	NPC193770
0.7681	Intermediate Similarity	NPC220210
0.7681	Intermediate Similarity	NPC20181
0.7667	Intermediate Similarity	NPC58970
0.7667	Intermediate Similarity	NPC176819
0.7667	Intermediate Similarity	NPC228776
0.7667	Intermediate Similarity	NPC32351
0.7667	Intermediate Similarity	NPC118788
0.7667	Intermediate Similarity	NPC163984
0.7662	Intermediate Similarity	NPC3511
0.7662	Intermediate Similarity	NPC142253
0.7656	Intermediate Similarity	NPC55004
0.7656	Intermediate Similarity	NPC193695
0.7656	Intermediate Similarity	NPC192427
0.7656	Intermediate Similarity	NPC267626
0.7656	Intermediate Similarity	NPC49575
0.7656	Intermediate Similarity	NPC230823
0.7639	Intermediate Similarity	NPC474488
0.7632	Intermediate Similarity	NPC26139
0.7619	Intermediate Similarity	NPC275472
0.7612	Intermediate Similarity	NPC167256
0.7606	Intermediate Similarity	NPC40574
0.76	Intermediate Similarity	NPC469996
0.7595	Intermediate Similarity	NPC474537
0.7581	Intermediate Similarity	NPC474141
0.7581	Intermediate Similarity	NPC296311
0.7581	Intermediate Similarity	NPC37644
0.7568	Intermediate Similarity	NPC19907
0.7564	Intermediate Similarity	NPC49019
0.7564	Intermediate Similarity	NPC118423
0.7532	Intermediate Similarity	NPC149237
0.7532	Intermediate Similarity	NPC278459
0.7532	Intermediate Similarity	NPC225515
0.75	Intermediate Similarity	NPC19900
0.75	Intermediate Similarity	NPC52449
0.75	Intermediate Similarity	NPC150162
0.75	Intermediate Similarity	NPC472490
0.75	Intermediate Similarity	NPC476177
0.75	Intermediate Similarity	NPC304983
0.75	Intermediate Similarity	NPC169275
0.7468	Intermediate Similarity	NPC87552
0.7467	Intermediate Similarity	NPC165711
0.7467	Intermediate Similarity	NPC266193
0.7467	Intermediate Similarity	NPC97377
0.7467	Intermediate Similarity	NPC257666
0.746	Intermediate Similarity	NPC63396
0.746	Intermediate Similarity	NPC202850
0.7436	Intermediate Similarity	NPC469799
0.7436	Intermediate Similarity	NPC469805
0.7436	Intermediate Similarity	NPC268122
0.7436	Intermediate Similarity	NPC472867
0.7436	Intermediate Similarity	NPC302661
0.7436	Intermediate Similarity	NPC103486
0.7436	Intermediate Similarity	NPC469806
0.7436	Intermediate Similarity	NPC469804
0.7436	Intermediate Similarity	NPC472239
0.7436	Intermediate Similarity	NPC238991
0.7403	Intermediate Similarity	NPC287063
0.7403	Intermediate Similarity	NPC472478
0.7403	Intermediate Similarity	NPC469798
0.7403	Intermediate Similarity	NPC469637
0.7403	Intermediate Similarity	NPC2482
0.7403	Intermediate Similarity	NPC469797
0.7397	Intermediate Similarity	NPC276336

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 NPC251118 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	2595
0.2-0.3	4246
0.3-0.4	1483
0.4-0.5	358
0.5-0.6	178
0.6-0.7	59
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
0.8657	High Similarity	NPD4691	Approved
0.8551	High Similarity	NPD4058	Approved
0.8551	High Similarity	NPD4687	Approved
0.8507	High Similarity	NPD4137	Phase 3
0.8382	Intermediate Similarity	NPD4747	Approved
0.8286	Intermediate Similarity	NPD5733	Approved
0.8261	Intermediate Similarity	NPD5276	Approved
0.8095	Intermediate Similarity	NPD287	Approved
0.7826	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD8028	Phase 2
0.75	Intermediate Similarity	NPD5690	Phase 2
0.7403	Intermediate Similarity	NPD4695	Discontinued
0.7215	Intermediate Similarity	NPD4221	Approved
0.7215	Intermediate Similarity	NPD4223	Phase 3
0.7195	Intermediate Similarity	NPD3573	Approved
0.7073	Intermediate Similarity	NPD5280	Approved
0.7073	Intermediate Similarity	NPD4519	Discontinued
0.7073	Intermediate Similarity	NPD4623	Approved
0.7073	Intermediate Similarity	NPD4694	Approved
0.7042	Intermediate Similarity	NPD7331	Phase 2
0.7037	Intermediate Similarity	NPD3666	Approved
0.7037	Intermediate Similarity	NPD4197	Approved
0.7037	Intermediate Similarity	NPD3665	Phase 1
0.7037	Intermediate Similarity	NPD3133	Approved
0.6951	Remote Similarity	NPD5329	Approved
0.6941	Remote Similarity	NPD5207	Approved
0.6923	Remote Similarity	NPD3617	Approved
0.6867	Remote Similarity	NPD4688	Approved
0.6867	Remote Similarity	NPD3618	Phase 1
0.6867	Remote Similarity	NPD5279	Phase 3
0.6867	Remote Similarity	NPD7146	Approved
0.6867	Remote Similarity	NPD5330	Approved
0.6867	Remote Similarity	NPD4689	Approved
0.6867	Remote Similarity	NPD5205	Approved
0.6867	Remote Similarity	NPD7521	Approved
0.6867	Remote Similarity	NPD6684	Approved
0.6867	Remote Similarity	NPD6409	Approved
0.6867	Remote Similarity	NPD4690	Approved
0.6867	Remote Similarity	NPD4693	Phase 3
0.6867	Remote Similarity	NPD7334	Approved
0.6867	Remote Similarity	NPD4138	Approved
0.6867	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5694	Approved
0.686	Remote Similarity	NPD5284	Approved
0.686	Remote Similarity	NPD5281	Approved
0.686	Remote Similarity	NPD6079	Approved
0.6835	Remote Similarity	NPD4195	Approved
0.679	Remote Similarity	NPD3667	Approved
0.675	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD1694	Approved
0.6744	Remote Similarity	NPD5692	Phase 3
0.6706	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6903	Approved
0.6706	Remote Similarity	NPD5208	Approved
0.6706	Remote Similarity	NPD5737	Approved
0.6706	Remote Similarity	NPD4518	Approved
0.6706	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD7341	Phase 2
0.6667	Remote Similarity	NPD6050	Approved
0.6629	Remote Similarity	NPD5210	Approved
0.6629	Remote Similarity	NPD4629	Approved
0.6628	Remote Similarity	NPD5328	Approved
0.6628	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6673	Approved
0.6628	Remote Similarity	NPD6904	Approved
0.6628	Remote Similarity	NPD4753	Phase 2
0.6628	Remote Similarity	NPD6080	Approved
0.6627	Remote Similarity	NPD4786	Approved
0.6627	Remote Similarity	NPD3668	Phase 3
0.6585	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5222	Approved
0.6556	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5221	Approved
0.6552	Remote Similarity	NPD4096	Approved
0.6484	Remote Similarity	NPD5173	Approved
0.6484	Remote Similarity	NPD3495	Discontinued
0.6479	Remote Similarity	NPD4192	Approved
0.6479	Remote Similarity	NPD4194	Approved
0.6479	Remote Similarity	NPD4193	Approved
0.6479	Remote Similarity	NPD4191	Approved
0.6477	Remote Similarity	NPD5693	Phase 1
0.6477	Remote Similarity	NPD7515	Phase 2
0.6471	Remote Similarity	NPD6098	Approved
0.6463	Remote Similarity	NPD4139	Approved
0.6463	Remote Similarity	NPD4692	Approved
0.6444	Remote Similarity	NPD5695	Phase 3
0.6404	Remote Similarity	NPD5133	Approved
0.6404	Remote Similarity	NPD7631	Approved
0.6404	Remote Similarity	NPD4202	Approved
0.6389	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7732	Phase 3
0.6374	Remote Similarity	NPD7614	Phase 1
0.6344	Remote Similarity	NPD4696	Approved
0.6344	Remote Similarity	NPD5286	Approved
0.6344	Remote Similarity	NPD5285	Approved
0.6333	Remote Similarity	NPD7900	Approved
0.6333	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6001	Approved
0.6333	Remote Similarity	NPD7748	Approved
0.6324	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD7609	Phase 3
0.6277	Remote Similarity	NPD5223	Approved
0.6264	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5654	Approved
0.6211	Remote Similarity	NPD5211	Phase 2
0.6211	Remote Similarity	NPD5225	Approved
0.6211	Remote Similarity	NPD5091	Approved
0.6211	Remote Similarity	NPD5226	Approved
0.6211	Remote Similarity	NPD5224	Approved
0.6211	Remote Similarity	NPD4633	Approved
0.6196	Remote Similarity	NPD4697	Phase 3
0.6154	Remote Similarity	NPD8262	Approved
0.6146	Remote Similarity	NPD5175	Approved
0.6146	Remote Similarity	NPD5174	Approved
0.6129	Remote Similarity	NPD6083	Phase 2
0.6129	Remote Similarity	NPD6084	Phase 2
0.6129	Remote Similarity	NPD5959	Approved
0.6129	Remote Similarity	NPD4755	Approved
0.6129	Remote Similarity	NPD7902	Approved
0.6125	Remote Similarity	NPD8039	Approved
0.6118	Remote Similarity	NPD4788	Approved
0.6098	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD5141	Approved
0.6064	Remote Similarity	NPD5696	Approved
0.6044	Remote Similarity	NPD6399	Phase 3
0.6023	Remote Similarity	NPD650	Approved
0.6	Remote Similarity	NPD6404	Discontinued
0.6	Remote Similarity	NPD5209	Approved
0.6	Remote Similarity	NPD4700	Approved
0.5977	Remote Similarity	NPD1696	Phase 3
0.5968	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.596	Remote Similarity	NPD6614	Approved
0.596	Remote Similarity	NPD5697	Approved
0.5934	Remote Similarity	NPD6411	Approved
0.5926	Remote Similarity	NPD8264	Approved
0.5918	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.59	Remote Similarity	NPD5168	Approved
0.59	Remote Similarity	NPD4729	Approved
0.59	Remote Similarity	NPD6899	Approved
0.59	Remote Similarity	NPD4730	Approved
0.59	Remote Similarity	NPD6011	Approved
0.59	Remote Similarity	NPD6881	Approved
0.5867	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD6014	Approved
0.5842	Remote Similarity	NPD6013	Approved
0.5842	Remote Similarity	NPD6012	Approved
0.5824	Remote Similarity	NPD5785	Approved
0.5816	Remote Similarity	NPD4754	Approved
0.5816	Remote Similarity	NPD6052	Approved
0.5806	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD5282	Discontinued
0.5802	Remote Similarity	NPD4785	Approved
0.5802	Remote Similarity	NPD4784	Approved
0.5795	Remote Similarity	NPD5363	Approved
0.5784	Remote Similarity	NPD5248	Approved
0.5784	Remote Similarity	NPD6883	Approved
0.5784	Remote Similarity	NPD5251	Approved
0.5784	Remote Similarity	NPD4634	Approved
0.5784	Remote Similarity	NPD5247	Approved
0.5784	Remote Similarity	NPD5135	Approved
0.5784	Remote Similarity	NPD5249	Phase 3
0.5784	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD5250	Approved
0.5784	Remote Similarity	NPD7290	Approved
0.5784	Remote Similarity	NPD7102	Approved
0.5784	Remote Similarity	NPD5169	Approved
0.5775	Remote Similarity	NPD4219	Approved
0.575	Remote Similarity	NPD4243	Approved
0.5743	Remote Similarity	NPD5128	Approved
0.5738	Remote Similarity	NPD5783	Phase 3
0.5735	Remote Similarity	NPD29	Approved
0.5735	Remote Similarity	NPD28	Approved
0.5728	Remote Similarity	NPD5217	Approved
0.5728	Remote Similarity	NPD6649	Approved
0.5728	Remote Similarity	NPD6617	Approved
0.5728	Remote Similarity	NPD8130	Phase 1
0.5728	Remote Similarity	NPD5215	Approved
0.5728	Remote Similarity	NPD5127	Approved
0.5728	Remote Similarity	NPD6869	Approved
0.5728	Remote Similarity	NPD5216	Approved
0.5728	Remote Similarity	NPD6847	Approved
0.5728	Remote Similarity	NPD6650	Approved
0.5714	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6101	Approved
0.57	Remote Similarity	NPD4768	Approved
0.57	Remote Similarity	NPD7128	Approved
0.57	Remote Similarity	NPD4767	Approved
0.57	Remote Similarity	NPD5739	Approved
0.57	Remote Similarity	NPD6008	Approved
0.57	Remote Similarity	NPD6402	Approved
0.57	Remote Similarity	NPD6675	Approved
0.5673	Remote Similarity	NPD8297	Approved
0.5673	Remote Similarity	NPD6882	Approved
0.567	Remote Similarity	NPD2066	Phase 3
0.5667	Remote Similarity	NPD319	Phase 1
0.5663	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD6412	Phase 2
0.5644	Remote Similarity	NPD5701	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