NPASS Compound

Structure

NPC241354 OpenBabel07101719242D 22 24 0 0 0 0 0 0 0 0999 V2000 1.0616 0.2112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4518 0.6013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6651 1.0457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1052 2.0080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0919 1.8580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1111 1.1111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1095 1.8772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5497 2.8395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3912 1.3492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 0.6013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5518 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 2.1727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6629 1.1111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1111 1.6629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5518 2.7741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6001 1.7016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5098 2.5629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5098 0.2112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2091 1.1140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0654 -0.6203 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.7741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 11 1 0 0 0 0 2 13 1 0 0 0 0 3 7 1 0 0 0 0 3 13 2 0 0 0 0 4 8 2 0 0 0 0 4 13 1 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 10 1 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 21 1 0 0 0 0 12 14 2 0 0 0 0 12 17 1 0 0 0 0 15 22 1 0 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 17 22 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.12
Volume:	310.921
LogP:	3.866
LogD:	3.492
LogS:	-5.091
# Rotatable Bonds:	0
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.755
Synthetic Accessibility Score:	4.314
Fsp3:	0.278
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:	-4.9
MDCK Permeability:	1.8496917618904263e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.109
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.139
Plasma Protein Binding (PPB):	97.7416000366211%
Volume Distribution (VD):	0.522
Pgp-substrate:	1.9190795421600342%

ADMET: Metabolism

CYP1A2-inhibitor:	0.988
CYP1A2-substrate:	0.19
CYP2C19-inhibitor:	0.973
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.914
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.883
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.725
CYP3A4-substrate:	0.494

ADMET: Excretion

Clearance (CL):	14.394
Half-life (T1/2):	0.795

ADMET: Toxicity

hERG Blockers:	0.431
Human Hepatotoxicity (H-HT):	0.082
Drug-inuced Liver Injury (DILI):	0.107
AMES Toxicity:	0.613
Rat Oral Acute Toxicity:	0.135
Maximum Recommended Daily Dose:	0.837
Skin Sensitization:	0.942
Carcinogencity:	0.76
Eye Corrosion:	0.004
Eye Irritation:	0.402
Respiratory Toxicity:	0.286

Download Data

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

Natural Product: NPC241354

Natural Product ID:	NPC241354
*Common Name:**	Corniculatolide A
IUPAC Name:	n.a.
Synonyms:	Corniculatolide A; Dihydro-Combretastatin D-2
Standard InCHIKey:	GTGFVTOGSQUFFF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H18O4/c19-16-9-5-14-6-10-18(20)21-11-1-2-13-3-7-15(8-4-13)22-17(16)12-14/h3-5,7-9,12,19H,1-2,6,10-11H2
SMILES:	O=C1OCCCc2ccc(Oc3cc(CC1)ccc3O)cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL562363
PubChem CID:	11770972
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001510] Lignan lactones

*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
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	rind	n.a.	DOI[10.1002/hlca.200800177]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1021/np50063a031]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np50063a031]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165134]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	n.a.	PMID[16254827]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	stem	n.a.	PMID[16254827]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17323995]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[17450509]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	seed kernels	n.a.	n.a.	PMID[19908853]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20411928]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22316191]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2778454]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31895570]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	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
ED50	1
IC50	1

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	>	100.0	ug ml-1	PMID[568472]
NPT2	Others	Unspecified		IC50	=	187200.0	nM	PMID[568474]

☑ 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 NPC241354 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	308
0.1-0.2	1479
0.2-0.3	4337
0.3-0.4	11412
0.4-0.5	6638
0.5-0.6	4131
0.6-0.7	8946
0.7-0.8	4936
0.8-0.85	397
0.85-0.9	105
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9512	High Similarity	NPC280767
0.944	High Similarity	NPC226661
0.9355	High Similarity	NPC3221
0.9302	High Similarity	NPC5310
0.9302	High Similarity	NPC300776
0.9302	High Similarity	NPC4982
0.9302	High Similarity	NPC68779
0.9302	High Similarity	NPC176814
0.92	High Similarity	NPC53305
0.92	High Similarity	NPC257589
0.9187	High Similarity	NPC177291
0.9187	High Similarity	NPC194416
0.916	High Similarity	NPC90431
0.9127	High Similarity	NPC84076
0.9127	High Similarity	NPC127937
0.9127	High Similarity	NPC213552
0.9127	High Similarity	NPC303680
0.9127	High Similarity	NPC90128
0.9127	High Similarity	NPC120225
0.9127	High Similarity	NPC92207
0.9084	High Similarity	NPC113295
0.9055	High Similarity	NPC151167
0.9055	High Similarity	NPC276466
0.9055	High Similarity	NPC123722
0.9055	High Similarity	NPC5018
0.9055	High Similarity	NPC123228
0.9048	High Similarity	NPC289459
0.9023	High Similarity	NPC284409
0.8992	High Similarity	NPC215941
0.8992	High Similarity	NPC137427
0.8992	High Similarity	NPC123196
0.8992	High Similarity	NPC65935
0.8992	High Similarity	NPC311419
0.8992	High Similarity	NPC244246
0.8992	High Similarity	NPC319282
0.8992	High Similarity	NPC275724
0.8976	High Similarity	NPC179777
0.8971	High Similarity	NPC160378
0.8968	High Similarity	NPC246704
0.8955	High Similarity	NPC288452
0.8955	High Similarity	NPC289690
0.8934	High Similarity	NPC86947
0.8931	High Similarity	NPC475468
0.8915	High Similarity	NPC304622
0.8915	High Similarity	NPC83062
0.8898	High Similarity	NPC87113
0.8889	High Similarity	NPC29599
0.8889	High Similarity	NPC166137
0.8889	High Similarity	NPC282291
0.8889	High Similarity	NPC163083
0.8889	High Similarity	NPC100675
0.888	High Similarity	NPC290451
0.888	High Similarity	NPC201777
0.888	High Similarity	NPC472271
0.888	High Similarity	NPC127389
0.8864	High Similarity	NPC471110
0.8862	High Similarity	NPC205502
0.8824	High Similarity	NPC253481
0.8824	High Similarity	NPC253722
0.8824	High Similarity	NPC31751
0.8819	High Similarity	NPC60517
0.8819	High Similarity	NPC146886
0.8819	High Similarity	NPC20443
0.8819	High Similarity	NPC288945
0.879	High Similarity	NPC299406
0.877	High Similarity	NPC51345
0.876	High Similarity	NPC281020
0.876	High Similarity	NPC20404
0.876	High Similarity	NPC223807
0.876	High Similarity	NPC12022
0.876	High Similarity	NPC20287
0.876	High Similarity	NPC293641
0.8759	High Similarity	NPC273657
0.8759	High Similarity	NPC106920
0.875	High Similarity	NPC326065
0.875	High Similarity	NPC194519
0.874	High Similarity	NPC242372
0.874	High Similarity	NPC257976
0.874	High Similarity	NPC4181
0.874	High Similarity	NPC164778
0.8731	High Similarity	NPC471664
0.8731	High Similarity	NPC471665
0.8722	High Similarity	NPC144662
0.8714	High Similarity	NPC472969
0.871	High Similarity	NPC470626
0.8696	High Similarity	NPC473090
0.8692	High Similarity	NPC110313
0.8692	High Similarity	NPC278308
0.8686	High Similarity	NPC52664
0.8682	High Similarity	NPC276014
0.8682	High Similarity	NPC191037
0.8682	High Similarity	NPC178284
0.8682	High Similarity	NPC58607
0.8672	High Similarity	NPC48990
0.8672	High Similarity	NPC312404
0.8672	High Similarity	NPC85565
0.8672	High Similarity	NPC293701
0.8672	High Similarity	NPC273686
0.8672	High Similarity	NPC114901
0.8667	High Similarity	NPC281780
0.8667	High Similarity	NPC126206
0.8661	High Similarity	NPC114298
0.8652	High Similarity	NPC98809
0.8652	High Similarity	NPC476394
0.8651	High Similarity	NPC207613
0.8651	High Similarity	NPC158949
0.8651	High Similarity	NPC204466
0.864	High Similarity	NPC263386
0.864	High Similarity	NPC141791
0.8636	High Similarity	NPC198388
0.8633	High Similarity	NPC53884
0.8633	High Similarity	NPC223185
0.8633	High Similarity	NPC258671
0.8629	High Similarity	NPC293619
0.8623	High Similarity	NPC470811
0.8623	High Similarity	NPC477697
0.8623	High Similarity	NPC477696
0.8615	High Similarity	NPC292056
0.8615	High Similarity	NPC118787
0.8615	High Similarity	NPC147821
0.8615	High Similarity	NPC319625
0.8615	High Similarity	NPC111247
0.8615	High Similarity	NPC183181
0.8615	High Similarity	NPC163332
0.8615	High Similarity	NPC41706
0.8594	High Similarity	NPC229084
0.8594	High Similarity	NPC106659
0.8594	High Similarity	NPC317769
0.8594	High Similarity	NPC18984
0.8594	High Similarity	NPC31344
0.8594	High Similarity	NPC160900
0.8594	High Similarity	NPC279379
0.8592	High Similarity	NPC221091
0.8592	High Similarity	NPC259576
0.8583	High Similarity	NPC343720
0.8583	High Similarity	NPC473853
0.8583	High Similarity	NPC113865
0.8583	High Similarity	NPC54872
0.8583	High Similarity	NPC70752
0.8583	High Similarity	NPC184651
0.8583	High Similarity	NPC470212
0.8583	High Similarity	NPC324571
0.8583	High Similarity	NPC312675
0.8583	High Similarity	NPC262156
0.8582	High Similarity	NPC135127
0.8582	High Similarity	NPC67247
0.8571	High Similarity	NPC117780
0.8571	High Similarity	NPC2058
0.8571	High Similarity	NPC61
0.8571	High Similarity	NPC25581
0.8571	High Similarity	NPC227217
0.8571	High Similarity	NPC165133
0.8571	High Similarity	NPC95614
0.8571	High Similarity	NPC5419
0.8571	High Similarity	NPC56214
0.8571	High Similarity	NPC242885
0.8571	High Similarity	NPC202474
0.8571	High Similarity	NPC232316
0.8571	High Similarity	NPC18074
0.8561	High Similarity	NPC172673
0.8561	High Similarity	NPC66905
0.8561	High Similarity	NPC304956
0.856	High Similarity	NPC275519
0.856	High Similarity	NPC159916
0.8551	High Similarity	NPC472332
0.8551	High Similarity	NPC472335
0.855	High Similarity	NPC72529
0.855	High Similarity	NPC478215
0.8538	High Similarity	NPC304630
0.8538	High Similarity	NPC17837
0.8531	High Similarity	NPC300329
0.8527	High Similarity	NPC109822
0.8527	High Similarity	NPC94276
0.8527	High Similarity	NPC74478
0.8519	High Similarity	NPC477301
0.8519	High Similarity	NPC204592
0.8519	High Similarity	NPC152209
0.8519	High Similarity	NPC470990
0.8516	High Similarity	NPC71090
0.8516	High Similarity	NPC85488
0.8511	High Similarity	NPC283081
0.8511	High Similarity	NPC221383
0.8511	High Similarity	NPC143892
0.8511	High Similarity	NPC299090
0.8507	High Similarity	NPC168799
0.8507	High Similarity	NPC155209
0.8507	High Similarity	NPC129889
0.8507	High Similarity	NPC307006
0.8504	High Similarity	NPC14007
0.8504	High Similarity	NPC269843
0.8504	High Similarity	NPC470848
0.8504	High Similarity	NPC470849
0.8504	High Similarity	NPC189844
0.8504	High Similarity	NPC109083
0.8504	High Similarity	NPC224814
0.8504	High Similarity	NPC60962
0.8496	Intermediate Similarity	NPC318799
0.8496	Intermediate Similarity	NPC469480
0.8492	Intermediate Similarity	NPC281298
0.8492	Intermediate Similarity	NPC264976

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 NPC241354 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	257
0.1-0.2	908
0.2-0.3	1604
0.3-0.4	2577
0.4-0.5	1809
0.5-0.6	1122
0.6-0.7	693
0.7-0.8	170
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8594	High Similarity	NPD4379	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD6798	Discontinued
0.8417	Intermediate Similarity	NPD4110	Phase 3
0.8417	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.8413	Intermediate Similarity	NPD1894	Discontinued
0.837	Intermediate Similarity	NPD6355	Discontinued
0.8358	Intermediate Similarity	NPD6233	Phase 2
0.8358	Intermediate Similarity	NPD4062	Phase 3
0.8296	Intermediate Similarity	NPD4060	Phase 1
0.8295	Intermediate Similarity	NPD1535	Discovery
0.8293	Intermediate Similarity	NPD228	Approved
0.8231	Intermediate Similarity	NPD1481	Phase 2
0.8209	Intermediate Similarity	NPD7095	Approved
0.8112	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD3027	Phase 3
0.806	Intermediate Similarity	NPD9494	Approved
0.8047	Intermediate Similarity	NPD5536	Phase 2
0.8028	Intermediate Similarity	NPD4628	Phase 3
0.8016	Intermediate Similarity	NPD5283	Phase 1
0.8015	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD1608	Approved
0.7923	Intermediate Similarity	NPD5585	Approved
0.7919	Intermediate Similarity	NPD1934	Approved
0.7899	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD1613	Approved
0.7887	Intermediate Similarity	NPD4534	Discontinued
0.7887	Intermediate Similarity	NPD5958	Discontinued
0.7881	Intermediate Similarity	NPD3882	Suspended
0.7868	Intermediate Similarity	NPD2614	Approved
0.7868	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD2801	Approved
0.7847	Intermediate Similarity	NPD6190	Approved
0.7842	Intermediate Similarity	NPD447	Suspended
0.7836	Intermediate Similarity	NPD1283	Approved
0.7815	Intermediate Similarity	NPD3817	Phase 2
0.7803	Intermediate Similarity	NPD3847	Discontinued
0.7795	Intermediate Similarity	NPD5535	Approved
0.7794	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD6653	Approved
0.7778	Intermediate Similarity	NPD2797	Approved
0.7778	Intermediate Similarity	NPD8166	Discontinued
0.7778	Intermediate Similarity	NPD6234	Discontinued
0.776	Intermediate Similarity	NPD2684	Approved
0.7748	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD2935	Discontinued
0.7746	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1511	Approved
0.7727	Intermediate Similarity	NPD1778	Approved
0.7727	Intermediate Similarity	NPD17	Approved
0.7721	Intermediate Similarity	NPD5647	Approved
0.7718	Intermediate Similarity	NPD3455	Phase 2
0.7698	Intermediate Similarity	NPD3022	Approved
0.7698	Intermediate Similarity	NPD3021	Approved
0.7677	Intermediate Similarity	NPD7199	Phase 2
0.7669	Intermediate Similarity	NPD3496	Discontinued
0.7656	Intermediate Similarity	NPD7843	Approved
0.7647	Intermediate Similarity	NPD1203	Approved
0.7643	Intermediate Similarity	NPD825	Approved
0.7643	Intermediate Similarity	NPD826	Approved
0.7643	Intermediate Similarity	NPD2979	Phase 3
0.7643	Intermediate Similarity	NPD1558	Phase 1
0.7635	Intermediate Similarity	NPD1512	Approved
0.763	Intermediate Similarity	NPD4359	Approved
0.7626	Intermediate Similarity	NPD3268	Approved
0.7622	Intermediate Similarity	NPD6032	Approved
0.7622	Intermediate Similarity	NPD4476	Approved
0.7622	Intermediate Similarity	NPD4477	Approved
0.7622	Intermediate Similarity	NPD2438	Suspended
0.7615	Intermediate Similarity	NPD7157	Approved
0.7612	Intermediate Similarity	NPD1281	Approved
0.76	Intermediate Similarity	NPD968	Approved
0.7597	Intermediate Similarity	NPD1241	Discontinued
0.7589	Intermediate Similarity	NPD4340	Discontinued
0.7589	Intermediate Similarity	NPD1933	Approved
0.7589	Intermediate Similarity	NPD230	Phase 1
0.7586	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7266	Discontinued
0.7568	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3146	Approved
0.7566	Intermediate Similarity	NPD37	Approved
0.7552	Intermediate Similarity	NPD2799	Discontinued
0.7547	Intermediate Similarity	NPD3818	Discontinued
0.754	Intermediate Similarity	NPD1358	Approved
0.7533	Intermediate Similarity	NPD1653	Approved
0.7532	Intermediate Similarity	NPD4965	Approved
0.7532	Intermediate Similarity	NPD6166	Phase 2
0.7532	Intermediate Similarity	NPD4967	Phase 2
0.7532	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4966	Approved
0.7531	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD1357	Approved
0.7519	Intermediate Similarity	NPD1651	Approved
0.7518	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD3620	Phase 2
0.7517	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD2239	Approved
0.75	Intermediate Similarity	NPD6799	Approved
0.75	Intermediate Similarity	NPD2240	Approved
0.7483	Intermediate Similarity	NPD7097	Phase 1
0.7482	Intermediate Similarity	NPD6832	Phase 2
0.7482	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD555	Phase 2
0.7464	Intermediate Similarity	NPD6584	Phase 3
0.7463	Intermediate Similarity	NPD5846	Approved
0.7463	Intermediate Similarity	NPD6516	Phase 2
0.7453	Intermediate Similarity	NPD7472	Approved
0.7453	Intermediate Similarity	NPD7074	Phase 3
0.7452	Intermediate Similarity	NPD8127	Discontinued
0.745	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD8032	Phase 2
0.7445	Intermediate Similarity	NPD3225	Approved
0.7438	Intermediate Similarity	NPD7228	Approved
0.7432	Intermediate Similarity	NPD7440	Discontinued
0.7431	Intermediate Similarity	NPD7033	Discontinued
0.7429	Intermediate Similarity	NPD5163	Phase 2
0.7417	Intermediate Similarity	NPD3686	Approved
0.7417	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3687	Approved
0.7415	Intermediate Similarity	NPD3750	Approved
0.7413	Intermediate Similarity	NPD2653	Approved
0.741	Intermediate Similarity	NPD454	Approved
0.741	Intermediate Similarity	NPD2861	Phase 2
0.7407	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6273	Approved
0.7394	Intermediate Similarity	NPD4140	Approved
0.7391	Intermediate Similarity	NPD5844	Phase 1
0.7386	Intermediate Similarity	NPD6386	Approved
0.7386	Intermediate Similarity	NPD6385	Approved
0.7379	Intermediate Similarity	NPD1551	Phase 2
0.7379	Intermediate Similarity	NPD1538	Phase 1
0.7379	Intermediate Similarity	NPD1519	Approved
0.7379	Intermediate Similarity	NPD1537	Approved
0.7379	Intermediate Similarity	NPD2531	Phase 2
0.7376	Intermediate Similarity	NPD2313	Discontinued
0.7372	Intermediate Similarity	NPD7075	Discontinued
0.7368	Intermediate Similarity	NPD3111	Phase 1
0.7365	Intermediate Similarity	NPD2354	Approved
0.7353	Intermediate Similarity	NPD3705	Approved
0.7351	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD6671	Approved
0.7347	Intermediate Similarity	NPD4162	Approved
0.7343	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD257	Approved
0.7338	Intermediate Similarity	NPD258	Approved
0.7333	Intermediate Similarity	NPD4626	Approved
0.7329	Intermediate Similarity	NPD5763	Approved
0.7329	Intermediate Similarity	NPD5762	Approved
0.7329	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4870	Approved
0.7324	Intermediate Similarity	NPD259	Phase 1
0.7324	Intermediate Similarity	NPD2674	Phase 3
0.7324	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD3134	Approved
0.7313	Intermediate Similarity	NPD1548	Phase 1
0.7313	Intermediate Similarity	NPD9545	Approved
0.731	Intermediate Similarity	NPD4308	Phase 3
0.7301	Intermediate Similarity	NPD6797	Phase 2
0.7299	Intermediate Similarity	NPD9717	Approved
0.7296	Intermediate Similarity	NPD6232	Discontinued
0.729	Intermediate Similarity	NPD8455	Phase 2
0.729	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD9569	Approved
0.7266	Intermediate Similarity	NPD987	Approved
0.7266	Intermediate Similarity	NPD290	Approved
0.7266	Intermediate Similarity	NPD3267	Approved
0.7266	Intermediate Similarity	NPD3266	Approved
0.726	Intermediate Similarity	NPD1522	Approved
0.726	Intermediate Similarity	NPD1523	Approved
0.7259	Intermediate Similarity	NPD5691	Approved
0.7256	Intermediate Similarity	NPD7251	Discontinued
0.7256	Intermediate Similarity	NPD7039	Approved
0.7256	Intermediate Similarity	NPD7685	Pre-registration
0.7256	Intermediate Similarity	NPD7038	Approved
0.7255	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3764	Approved
0.7248	Intermediate Similarity	NPD3887	Approved
0.7246	Intermediate Similarity	NPD6582	Phase 2
0.7246	Intermediate Similarity	NPD2982	Phase 2
0.7246	Intermediate Similarity	NPD2983	Phase 2
0.7246	Intermediate Similarity	NPD6583	Phase 3
0.7246	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5402	Approved
0.7241	Intermediate Similarity	NPD1536	Approved
0.7237	Intermediate Similarity	NPD5403	Approved
0.7234	Intermediate Similarity	NPD4908	Phase 1
0.723	Intermediate Similarity	NPD3060	Approved
0.7226	Intermediate Similarity	NPD422	Phase 1
0.7226	Intermediate Similarity	NPD1610	Phase 2
0.7219	Intermediate Similarity	NPD3536	Discontinued
0.7212	Intermediate Similarity	NPD7808	Phase 3
0.7211	Intermediate Similarity	NPD2346	Discontinued
0.7211	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1550	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