NPASS Compound

Structure

CID292589 OpenBabel06191716102D 30 34 0 0 1 0 0 0 0 0999 V2000 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 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 -2.5981 -0.5000 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 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 2.5981 1.5000 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 1.7321 -1.0000 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 -1.5000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 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 -3.4641 -3.0000 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 -4.3301 -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 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 19 2 0 0 0 0 8 22 2 0 0 0 0 9 10 1 0 0 0 0 9 17 2 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 18 19 1 0 0 0 0 18 24 2 0 0 0 0 19 20 1 0 0 0 0 20 26 1 0 0 0 0 21 24 1 0 0 0 0 21 29 2 0 0 0 0 22 26 1 0 0 0 0 22 27 1 0 0 0 0 23 25 1 6 0 0 0 23 28 1 0 0 0 0 24 30 1 0 0 0 0 25 3 1 1 0 0 0 26 4 1 1 0 0 0 27 28 1 1 0 0 0 28 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.27
Volume:	451.823
LogP:	6.523
LogD:	4.125
LogS:	-4.679
# Rotatable Bonds:	0
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.446
Synthetic Accessibility Score:	5.034
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.878
MDCK Permeability:	2.0279350792407058e-05
Pgp-inhibitor:	0.393
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	96.71961212158203%
Volume Distribution (VD):	4.596
Pgp-substrate:	6.471694469451904%

ADMET: Metabolism

CYP1A2-inhibitor:	0.187
CYP1A2-substrate:	0.672
CYP2C19-inhibitor:	0.222
CYP2C19-substrate:	0.839
CYP2C9-inhibitor:	0.209
CYP2C9-substrate:	0.266
CYP2D6-inhibitor:	0.761
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.465
CYP3A4-substrate:	0.911

ADMET: Excretion

Clearance (CL):	11.928
Half-life (T1/2):	0.309

ADMET: Toxicity

hERG Blockers:	0.109
Human Hepatotoxicity (H-HT):	0.489
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.123
Rat Oral Acute Toxicity:	0.447
Maximum Recommended Daily Dose:	0.86
Skin Sensitization:	0.78
Carcinogencity:	0.839
Eye Corrosion:	0.003
Eye Irritation:	0.137
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC292589

Natural Product ID:	NPC292589
*Common Name:**	Iguesterin
IUPAC Name:	(6aS,6bS,8aS,12aR,14aR)-3-hydroxy-4,6a,6b,8a,11,14a-hexamethyl-8,9,12,12a,13,14-hexahydro-7H-picen-2-one
Synonyms:	Iguesterin
Standard InCHIKey:	FLMDVQMCMIGPEK-IPTPSVHJSA-N
Standard InCHI:	InChI=1S/C28H36O2/c1-17-9-10-25(3)11-13-27(5)22-8-7-19-18(2)24(30)21(29)16-20(19)26(22,4)12-14-28(27,6)23(25)15-17/h7-9,16,23,30H,10-15H2,1-6H3/t23-,25-,26+,27-,28+/m1/s1
SMILES:	CC1=CC[C@]2(C)CC[C@]3(C)C4=CC=C5C(=C(C(=O)C=C5[C@]4(C)CC[C@@]3(C)[C@@H]2C1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1092796
PubChem CID:	46881919
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic 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
NPO24927	Calyx podatypa	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843583]
NPO25232	Peperomia heyneana	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17291043]
NPO24927	Calyx podatypa	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791477]
NPO27395	Mandragora officinarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27107	Coleus coerulescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24927	Calyx podatypa	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26370	Iryanthera juruensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24417	Centaurea hololeuca	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25232	Peperomia heyneana	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16903	Chisocheton siamensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25293	Beaumontia brevituba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26578	Astragalus pamirensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8818	Rohdea wattii	Species	Asparagaceae	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
Ki	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1595	Individual Protein	Replicase polyprotein 1ab	SARS coronavirus	IC50	=	2600.0	nM	PMID[540116]
NPT1595	Individual Protein	Replicase polyprotein 1ab	SARS coronavirus	Ki	=	800.0	nM	PMID[540116]

☑ 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 NPC292589 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	1622
0.2-0.3	8332
0.3-0.4	18318
0.4-0.5	8324
0.5-0.6	4583
0.6-0.7	1255
0.7-0.8	88
0.8-0.85	4
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9718	High Similarity	NPC112680
0.9079	High Similarity	NPC470034
0.8947	High Similarity	NPC287063
0.8831	High Similarity	NPC475863
0.8734	High Similarity	NPC53385
0.8625	High Similarity	NPC33881
0.8608	High Similarity	NPC309309
0.8608	High Similarity	NPC291999
0.8333	Intermediate Similarity	NPC27817
0.8182	Intermediate Similarity	NPC1254
0.8148	Intermediate Similarity	NPC53733
0.8	Intermediate Similarity	NPC65615
0.8	Intermediate Similarity	NPC112454
0.8	Intermediate Similarity	NPC68148
0.7949	Intermediate Similarity	NPC110725
0.7931	Intermediate Similarity	NPC263780
0.7901	Intermediate Similarity	NPC225515
0.7841	Intermediate Similarity	NPC474328
0.7816	Intermediate Similarity	NPC174167
0.7816	Intermediate Similarity	NPC470036
0.7778	Intermediate Similarity	NPC108955
0.775	Intermediate Similarity	NPC189485
0.7727	Intermediate Similarity	NPC211230
0.7683	Intermediate Similarity	NPC55869
0.7683	Intermediate Similarity	NPC99308
0.7662	Intermediate Similarity	NPC190035
0.764	Intermediate Similarity	NPC474882
0.7632	Intermediate Similarity	NPC474060
0.7561	Intermediate Similarity	NPC18955
0.7556	Intermediate Similarity	NPC777
0.7529	Intermediate Similarity	NPC469993
0.75	Intermediate Similarity	NPC26504
0.75	Intermediate Similarity	NPC212369
0.75	Intermediate Similarity	NPC92080
0.75	Intermediate Similarity	NPC310992
0.747	Intermediate Similarity	NPC121984
0.7444	Intermediate Similarity	NPC23170
0.7403	Intermediate Similarity	NPC286814
0.7375	Intermediate Similarity	NPC473171
0.7368	Intermediate Similarity	NPC176107
0.7363	Intermediate Similarity	NPC147232
0.7349	Intermediate Similarity	NPC2482
0.7326	Intermediate Similarity	NPC263997
0.7326	Intermediate Similarity	NPC474537
0.7326	Intermediate Similarity	NPC8518
0.7326	Intermediate Similarity	NPC241512
0.7326	Intermediate Similarity	NPC6185
0.7326	Intermediate Similarity	NPC132228
0.7317	Intermediate Similarity	NPC30321
0.7294	Intermediate Similarity	NPC105803
0.7294	Intermediate Similarity	NPC70834
0.7273	Intermediate Similarity	NPC142754
0.7273	Intermediate Similarity	NPC296697
0.7273	Intermediate Similarity	NPC188292
0.7273	Intermediate Similarity	NPC87141
0.7273	Intermediate Similarity	NPC260474
0.7273	Intermediate Similarity	NPC39157
0.7273	Intermediate Similarity	NPC82477
0.7262	Intermediate Similarity	NPC6663
0.7262	Intermediate Similarity	NPC471898
0.7253	Intermediate Similarity	NPC160413
0.725	Intermediate Similarity	NPC147438
0.7237	Intermediate Similarity	NPC92327
0.7237	Intermediate Similarity	NPC242945
0.7237	Intermediate Similarity	NPC259156
0.7222	Intermediate Similarity	NPC60772
0.7215	Intermediate Similarity	NPC225467
0.7215	Intermediate Similarity	NPC181204
0.7209	Intermediate Similarity	NPC87552
0.7209	Intermediate Similarity	NPC96095
0.7191	Intermediate Similarity	NPC210216
0.7179	Intermediate Similarity	NPC139397
0.7176	Intermediate Similarity	NPC310989
0.7176	Intermediate Similarity	NPC251779
0.7176	Intermediate Similarity	NPC69101
0.7176	Intermediate Similarity	NPC103486
0.7159	Intermediate Similarity	NPC470523
0.7143	Intermediate Similarity	NPC242637
0.7143	Intermediate Similarity	NPC220210
0.7143	Intermediate Similarity	NPC20181
0.7126	Intermediate Similarity	NPC474680
0.7126	Intermediate Similarity	NPC133652
0.7126	Intermediate Similarity	NPC32037
0.7126	Intermediate Similarity	NPC255174
0.7125	Intermediate Similarity	NPC474228
0.7125	Intermediate Similarity	NPC474488
0.7125	Intermediate Similarity	NPC303613
0.7108	Intermediate Similarity	NPC72507
0.7108	Intermediate Similarity	NPC476808
0.7105	Intermediate Similarity	NPC107258
0.7093	Intermediate Similarity	NPC82538
0.7093	Intermediate Similarity	NPC237795
0.7089	Intermediate Similarity	NPC251929
0.7089	Intermediate Similarity	NPC265782
0.7089	Intermediate Similarity	NPC2634
0.7089	Intermediate Similarity	NPC282593
0.7089	Intermediate Similarity	NPC260040
0.7089	Intermediate Similarity	NPC307176
0.7089	Intermediate Similarity	NPC159577
0.7089	Intermediate Similarity	NPC35734
0.7079	Intermediate Similarity	NPC470524
0.7073	Intermediate Similarity	NPC474463
0.7059	Intermediate Similarity	NPC274050
0.7059	Intermediate Similarity	NPC3915
0.7059	Intermediate Similarity	NPC142244
0.7059	Intermediate Similarity	NPC474085
0.7059	Intermediate Similarity	NPC475833
0.7059	Intermediate Similarity	NPC162632
0.7059	Intermediate Similarity	NPC278459
0.7059	Intermediate Similarity	NPC267691
0.7059	Intermediate Similarity	NPC4166
0.7059	Intermediate Similarity	NPC263272
0.7051	Intermediate Similarity	NPC216460
0.7045	Intermediate Similarity	NPC94666
0.7037	Intermediate Similarity	NPC474796
0.7037	Intermediate Similarity	NPC219232
0.7037	Intermediate Similarity	NPC22134
0.7037	Intermediate Similarity	NPC474797
0.7037	Intermediate Similarity	NPC329866
0.7037	Intermediate Similarity	NPC128346
0.7024	Intermediate Similarity	NPC192329
0.7024	Intermediate Similarity	NPC170394
0.7024	Intermediate Similarity	NPC170793
0.7011	Intermediate Similarity	NPC472265
0.7011	Intermediate Similarity	NPC144258
0.7011	Intermediate Similarity	NPC237712
0.7011	Intermediate Similarity	NPC180834
0.7011	Intermediate Similarity	NPC33913
0.7	Intermediate Similarity	NPC115023
0.7	Intermediate Similarity	NPC470078
0.7	Intermediate Similarity	NPC54123
0.7	Intermediate Similarity	NPC474918
0.7	Intermediate Similarity	NPC474539
0.6988	Remote Similarity	NPC165711
0.6977	Remote Similarity	NPC311092
0.6977	Remote Similarity	NPC142253
0.6977	Remote Similarity	NPC472867
0.6977	Remote Similarity	NPC3511
0.6977	Remote Similarity	NPC472239
0.6977	Remote Similarity	NPC320514
0.6974	Remote Similarity	NPC4638
0.6974	Remote Similarity	NPC469662
0.6962	Remote Similarity	NPC256846
0.6951	Remote Similarity	NPC293803
0.6951	Remote Similarity	NPC175079
0.6941	Remote Similarity	NPC74086
0.6941	Remote Similarity	NPC476809
0.6939	Remote Similarity	NPC213366
0.6933	Remote Similarity	NPC469728
0.6932	Remote Similarity	NPC469948
0.6932	Remote Similarity	NPC33663
0.6923	Remote Similarity	NPC129913
0.6923	Remote Similarity	NPC38952
0.6914	Remote Similarity	NPC56747
0.6914	Remote Similarity	NPC109576
0.6914	Remote Similarity	NPC471799
0.6914	Remote Similarity	NPC470044
0.6914	Remote Similarity	NPC470045
0.6914	Remote Similarity	NPC180015
0.6914	Remote Similarity	NPC251705
0.6914	Remote Similarity	NPC130016
0.6905	Remote Similarity	NPC99168
0.6905	Remote Similarity	NPC470396
0.6905	Remote Similarity	NPC22955
0.6905	Remote Similarity	NPC275494
0.6905	Remote Similarity	NPC82635
0.6905	Remote Similarity	NPC474989
0.6905	Remote Similarity	NPC115515
0.6905	Remote Similarity	NPC471409
0.6897	Remote Similarity	NPC3856
0.6897	Remote Similarity	NPC83569
0.6897	Remote Similarity	NPC102197
0.6897	Remote Similarity	NPC41539
0.6897	Remote Similarity	NPC69279
0.6897	Remote Similarity	NPC470015
0.6897	Remote Similarity	NPC168188
0.6897	Remote Similarity	NPC279639
0.6889	Remote Similarity	NPC230387
0.6883	Remote Similarity	NPC251118
0.6867	Remote Similarity	NPC309399
0.6867	Remote Similarity	NPC69408
0.6867	Remote Similarity	NPC180886
0.6867	Remote Similarity	NPC106364
0.686	Remote Similarity	NPC473217
0.686	Remote Similarity	NPC44963
0.686	Remote Similarity	NPC189237
0.686	Remote Similarity	NPC6434
0.686	Remote Similarity	NPC472684
0.686	Remote Similarity	NPC116797
0.6854	Remote Similarity	NPC31564
0.6854	Remote Similarity	NPC474778
0.6854	Remote Similarity	NPC327115
0.6854	Remote Similarity	NPC474732
0.6854	Remote Similarity	NPC51014
0.6854	Remote Similarity	NPC222613
0.6854	Remote Similarity	NPC118648
0.6854	Remote Similarity	NPC474733
0.6854	Remote Similarity	NPC145879
0.6854	Remote Similarity	NPC475022
0.6848	Remote Similarity	NPC301244

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 NPC292589 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1689
0.2-0.3	4647
0.3-0.4	2033
0.4-0.5	336
0.5-0.6	172
0.6-0.7	100
0.7-0.8	8
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
0.8	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4695	Discontinued
0.7468	Intermediate Similarity	NPD5733	Approved
0.725	Intermediate Similarity	NPD4058	Approved
0.725	Intermediate Similarity	NPD4687	Approved
0.7241	Intermediate Similarity	NPD4694	Approved
0.7241	Intermediate Similarity	NPD5280	Approved
0.7215	Intermediate Similarity	NPD5276	Approved
0.7179	Intermediate Similarity	NPD4137	Phase 3
0.7126	Intermediate Similarity	NPD5329	Approved
0.7108	Intermediate Similarity	NPD3617	Approved
0.7089	Intermediate Similarity	NPD4691	Approved
0.7089	Intermediate Similarity	NPD4747	Approved
0.7045	Intermediate Similarity	NPD5279	Phase 3
0.7024	Intermediate Similarity	NPD4195	Approved
0.7011	Intermediate Similarity	NPD4197	Approved
0.6941	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8028	Phase 2
0.6854	Remote Similarity	NPD5690	Phase 2
0.6782	Remote Similarity	NPD4221	Approved
0.6782	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD7515	Phase 2
0.663	Remote Similarity	NPD4753	Phase 2
0.6629	Remote Similarity	NPD4786	Approved
0.6629	Remote Similarity	NPD3665	Phase 1
0.6629	Remote Similarity	NPD3666	Approved
0.6629	Remote Similarity	NPD3133	Approved
0.6628	Remote Similarity	NPD7645	Phase 2
0.6627	Remote Similarity	NPD4784	Approved
0.6627	Remote Similarity	NPD4785	Approved
0.6625	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5133	Approved
0.6591	Remote Similarity	NPD3667	Approved
0.6585	Remote Similarity	NPD4243	Approved
0.6548	Remote Similarity	NPD8264	Approved
0.6548	Remote Similarity	NPD6942	Approved
0.6548	Remote Similarity	NPD7339	Approved
0.6543	Remote Similarity	NPD6923	Approved
0.6543	Remote Similarity	NPD6922	Approved
0.6526	Remote Similarity	NPD7748	Approved
0.6522	Remote Similarity	NPD4518	Approved
0.6517	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD4194	Approved
0.6494	Remote Similarity	NPD4191	Approved
0.6494	Remote Similarity	NPD4192	Approved
0.6494	Remote Similarity	NPD4193	Approved
0.6489	Remote Similarity	NPD5284	Approved
0.6489	Remote Similarity	NPD6050	Approved
0.6489	Remote Similarity	NPD5281	Approved
0.6484	Remote Similarity	NPD4519	Discontinued
0.6484	Remote Similarity	NPD4690	Approved
0.6484	Remote Similarity	NPD4689	Approved
0.6484	Remote Similarity	NPD4138	Approved
0.6484	Remote Similarity	NPD4693	Phase 3
0.6484	Remote Similarity	NPD3618	Phase 1
0.6484	Remote Similarity	NPD4623	Approved
0.6484	Remote Similarity	NPD4688	Approved
0.6484	Remote Similarity	NPD5205	Approved
0.6471	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD7144	Approved
0.6463	Remote Similarity	NPD7143	Approved
0.6452	Remote Similarity	NPD5328	Approved
0.6429	Remote Similarity	NPD6924	Approved
0.6429	Remote Similarity	NPD6926	Approved
0.6392	Remote Similarity	NPD7614	Phase 1
0.6386	Remote Similarity	NPD7152	Approved
0.6386	Remote Similarity	NPD7150	Approved
0.6386	Remote Similarity	NPD7151	Approved
0.6383	Remote Similarity	NPD4096	Approved
0.6383	Remote Similarity	NPD5692	Phase 3
0.6344	Remote Similarity	NPD6672	Approved
0.6344	Remote Similarity	NPD5737	Approved
0.6327	Remote Similarity	NPD6084	Phase 2
0.6327	Remote Similarity	NPD6083	Phase 2
0.6327	Remote Similarity	NPD7902	Approved
0.6316	Remote Similarity	NPD6079	Approved
0.6316	Remote Similarity	NPD5694	Approved
0.6316	Remote Similarity	NPD287	Approved
0.6304	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5695	Phase 3
0.6289	Remote Similarity	NPD5210	Approved
0.6289	Remote Similarity	NPD4629	Approved
0.6279	Remote Similarity	NPD6933	Approved
0.6277	Remote Similarity	NPD6080	Approved
0.6277	Remote Similarity	NPD6904	Approved
0.6277	Remote Similarity	NPD6673	Approved
0.6224	Remote Similarity	NPD4697	Phase 3
0.6224	Remote Similarity	NPD5222	Approved
0.6224	Remote Similarity	NPD5221	Approved
0.6224	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5776	Phase 2
0.6207	Remote Similarity	NPD6932	Approved
0.6207	Remote Similarity	NPD6925	Approved
0.6196	Remote Similarity	NPD1696	Phase 3
0.617	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD5275	Approved
0.6163	Remote Similarity	NPD4190	Phase 3
0.6162	Remote Similarity	NPD4755	Approved
0.6162	Remote Similarity	NPD5173	Approved
0.6136	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD7145	Approved
0.6129	Remote Similarity	NPD5330	Approved
0.6129	Remote Similarity	NPD7146	Approved
0.6129	Remote Similarity	NPD6409	Approved
0.6129	Remote Similarity	NPD7334	Approved
0.6129	Remote Similarity	NPD6098	Approved
0.6129	Remote Similarity	NPD6684	Approved
0.6129	Remote Similarity	NPD7521	Approved
0.61	Remote Similarity	NPD5696	Approved
0.6087	Remote Similarity	NPD3668	Phase 3
0.6082	Remote Similarity	NPD6399	Phase 3
0.6082	Remote Similarity	NPD4202	Approved
0.6067	Remote Similarity	NPD6929	Approved
0.6067	Remote Similarity	NPD6683	Phase 2
0.6064	Remote Similarity	NPD3573	Approved
0.6042	Remote Similarity	NPD5207	Approved
0.604	Remote Similarity	NPD4700	Approved
0.604	Remote Similarity	NPD5286	Approved
0.604	Remote Similarity	NPD5285	Approved
0.604	Remote Similarity	NPD4696	Approved
0.602	Remote Similarity	NPD7900	Approved
0.602	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7525	Registered
0.6	Remote Similarity	NPD6930	Phase 2
0.6	Remote Similarity	NPD6903	Approved
0.6	Remote Similarity	NPD7509	Discontinued
0.6	Remote Similarity	NPD6931	Approved
0.6	Remote Similarity	NPD7332	Phase 2
0.6	Remote Similarity	NPD7514	Phase 3
0.598	Remote Similarity	NPD5223	Approved
0.5979	Remote Similarity	NPD5693	Phase 1
0.5978	Remote Similarity	NPD4788	Approved
0.5976	Remote Similarity	NPD7331	Phase 2
0.5972	Remote Similarity	NPD8262	Approved
0.5962	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5654	Approved
0.5934	Remote Similarity	NPD4139	Approved
0.5934	Remote Similarity	NPD6902	Approved
0.5934	Remote Similarity	NPD4692	Approved
0.5934	Remote Similarity	NPD6898	Phase 1
0.5922	Remote Similarity	NPD5211	Phase 2
0.5922	Remote Similarity	NPD5226	Approved
0.5922	Remote Similarity	NPD5224	Approved
0.5922	Remote Similarity	NPD5225	Approved
0.5922	Remote Similarity	NPD5091	Approved
0.5922	Remote Similarity	NPD4633	Approved
0.5905	Remote Similarity	NPD7128	Approved
0.5905	Remote Similarity	NPD5739	Approved
0.5905	Remote Similarity	NPD6402	Approved
0.5905	Remote Similarity	NPD6675	Approved
0.59	Remote Similarity	NPD7732	Phase 3
0.5882	Remote Similarity	NPD6404	Discontinued
0.5865	Remote Similarity	NPD4754	Approved
0.5865	Remote Similarity	NPD5175	Approved
0.5865	Remote Similarity	NPD5174	Approved
0.5844	Remote Similarity	NPD4219	Approved
0.5842	Remote Similarity	NPD5959	Approved
0.5833	Remote Similarity	NPD5208	Approved
0.5816	Remote Similarity	NPD6411	Approved
0.581	Remote Similarity	NPD5141	Approved
0.5806	Remote Similarity	NPD6695	Phase 3
0.5802	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7320	Approved
0.5794	Remote Similarity	NPD6899	Approved
0.5794	Remote Similarity	NPD6881	Approved
0.5784	Remote Similarity	NPD5290	Discontinued
0.5755	Remote Similarity	NPD4768	Approved
0.5755	Remote Similarity	NPD4767	Approved
0.5745	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD6373	Approved
0.5741	Remote Similarity	NPD6372	Approved
0.5732	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD5701	Approved
0.5701	Remote Similarity	NPD5697	Approved
0.5701	Remote Similarity	NPD6412	Phase 2
0.5698	Remote Similarity	NPD6939	Phase 2
0.5698	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD7102	Approved
0.5688	Remote Similarity	NPD7290	Approved
0.5688	Remote Similarity	NPD6883	Approved
0.5686	Remote Similarity	NPD3495	Discontinued
0.5684	Remote Similarity	NPD6893	Approved
0.5663	Remote Similarity	NPD7341	Phase 2
0.5657	Remote Similarity	NPD7637	Suspended
0.5652	Remote Similarity	NPD4748	Discontinued
0.5648	Remote Similarity	NPD5168	Approved
0.5648	Remote Similarity	NPD6011	Approved
0.5648	Remote Similarity	NPD4729	Approved
0.5648	Remote Similarity	NPD5128	Approved
0.5648	Remote Similarity	NPD4730	Approved
0.5644	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD6049	Phase 2
0.5636	Remote Similarity	NPD6650	Approved
0.5636	Remote Similarity	NPD6649	Approved
0.5636	Remote Similarity	NPD6847	Approved
0.5636	Remote Similarity	NPD8130	Phase 1
0.5636	Remote Similarity	NPD6617	Approved
0.5636	Remote Similarity	NPD6401	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