NPASS Compound

Structure

NPC228842 OpenBabel07101719512D 25 28 0 0 1 0 0 0 0 0999 V2000 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -1.2321 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 1.3660 -0.3660 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 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 1.5000 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 -5.0029 -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 -2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -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 1 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3660 -0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 14 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 7 16 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 24 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 1 1 1 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 22 2 0 0 0 0 14 25 1 0 0 0 0 15 6 1 1 0 0 0 15 17 1 0 0 0 0 16 18 2 0 0 0 0 17 19 1 6 0 0 0 18 24 1 0 0 0 0 19 21 1 6 0 0 0 20 21 1 6 0 0 0 20 25 1 0 0 0 0 21 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.21
Volume:	364.798
LogP:	3.606
LogD:	3.39
LogS:	-4.418
# Rotatable Bonds:	2
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.774
Synthetic Accessibility Score:	4.792
Fsp3:	0.762
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:	-4.661
MDCK Permeability:	2.3660448277951218e-05
Pgp-inhibitor:	0.402
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.073

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.243
Plasma Protein Binding (PPB):	92.37711334228516%
Volume Distribution (VD):	1.536
Pgp-substrate:	8.000448226928711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.665
CYP1A2-substrate:	0.505
CYP2C19-inhibitor:	0.637
CYP2C19-substrate:	0.869
CYP2C9-inhibitor:	0.232
CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.083
CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.933
CYP3A4-substrate:	0.863

ADMET: Excretion

Clearance (CL):	10.348
Half-life (T1/2):	0.197

ADMET: Toxicity

hERG Blockers:	0.8
Human Hepatotoxicity (H-HT):	0.533
Drug-inuced Liver Injury (DILI):	0.847
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.738
Maximum Recommended Daily Dose:	0.449
Skin Sensitization:	0.276
Carcinogencity:	0.845
Eye Corrosion:	0.004
Eye Irritation:	0.019
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC228842

Natural Product ID:	NPC228842
*Common Name:**	Caesaldekarin C
IUPAC Name:	[(4S,4aS,6aS,7R,11aS,11bR)-4a-hydroxy-4,7,11b-trimethyl-2,3,5,6,6a,7,11,11a-octahydro-1H-naphtho[2,1-f][1]benzofuran-4-yl] acetate
Synonyms:
Standard InCHIKey:	BDKARMILWOSVNF-ISBFPKGDSA-N
Standard InCHI:	InChI=1S/C21H30O4/c1-13-15-6-10-21(23)19(3,8-5-9-20(21,4)25-14(2)22)17(15)12-18-16(13)7-11-24-18/h7,11,13,15,17,23H,5-6,8-10,12H2,1-4H3/t13-,15+,17+,19-,20+,21+/m1/s1
SMILES:	C[C@@H]1[C@@H]2CC[C@@]3([C@](C)(CCC[C@]3(C)OC(=O)C)[C@H]2Cc2c1cco2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2381690
PubChem CID:	73356480
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO33322	caesalpinia volkensii	Species	Fabaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[23562058]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	30690.0	nM	PMID[544138]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	34440.0	nM	PMID[544138]

☑ 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 NPC228842 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	316
0.1-0.2	1311
0.2-0.3	2564
0.3-0.4	5184
0.4-0.5	10614
0.5-0.6	8118
0.6-0.7	8497
0.7-0.8	5592
0.8-0.85	359
0.85-0.9	98
0.9-0.95	36
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9724	High Similarity	NPC121615
0.9724	High Similarity	NPC294511
0.9595	High Similarity	NPC194499
0.9595	High Similarity	NPC7059
0.9595	High Similarity	NPC88007
0.9514	High Similarity	NPC71821
0.9467	High Similarity	NPC287559
0.9467	High Similarity	NPC8389
0.9463	High Similarity	NPC195954
0.9452	High Similarity	NPC212257
0.9437	High Similarity	NPC263337
0.9404	High Similarity	NPC68848
0.9404	High Similarity	NPC79571
0.9404	High Similarity	NPC18986
0.9342	High Similarity	NPC283209
0.9342	High Similarity	NPC285567
0.9276	High Similarity	NPC188649
0.9225	High Similarity	NPC202260
0.9221	High Similarity	NPC121995
0.9221	High Similarity	NPC277618
0.9216	High Similarity	NPC88841
0.9216	High Similarity	NPC288602
0.9139	High Similarity	NPC41880
0.9139	High Similarity	NPC104736
0.9103	High Similarity	NPC296558
0.9085	High Similarity	NPC307401
0.9079	High Similarity	NPC304692
0.9038	High Similarity	NPC41689
0.9032	High Similarity	NPC56358
0.8993	High Similarity	NPC125182
0.8993	High Similarity	NPC69647
0.8986	High Similarity	NPC255414
0.8954	High Similarity	NPC81405
0.8917	High Similarity	NPC270312
0.8904	High Similarity	NPC121158
0.8897	High Similarity	NPC148374
0.8896	High Similarity	NPC140952
0.8896	High Similarity	NPC84349
0.8896	High Similarity	NPC474611
0.8867	High Similarity	NPC211625
0.8861	High Similarity	NPC255787
0.8859	High Similarity	NPC216755
0.8854	High Similarity	NPC308156
0.8824	High Similarity	NPC155939
0.8824	High Similarity	NPC141538
0.8824	High Similarity	NPC296807
0.8816	High Similarity	NPC268905
0.8816	High Similarity	NPC246164
0.8803	High Similarity	NPC293253
0.8784	High Similarity	NPC251865
0.8782	High Similarity	NPC471003
0.8774	High Similarity	NPC123153
0.875	High Similarity	NPC46896
0.8742	High Similarity	NPC291742
0.8742	High Similarity	NPC234494
0.8734	High Similarity	NPC475779
0.8733	High Similarity	NPC471174
0.8726	High Similarity	NPC14499
0.8726	High Similarity	NPC476035
0.8726	High Similarity	NPC475039
0.8725	High Similarity	NPC5676
0.8718	High Similarity	NPC472299
0.871	High Similarity	NPC299038
0.8701	High Similarity	NPC92979
0.8688	High Similarity	NPC118086
0.8679	High Similarity	NPC310572
0.8667	High Similarity	NPC233763
0.8654	High Similarity	NPC475967
0.8654	High Similarity	NPC472823
0.8639	High Similarity	NPC67003
0.8639	High Similarity	NPC90296
0.8636	High Similarity	NPC98206
0.8636	High Similarity	NPC237259
0.8636	High Similarity	NPC302054
0.8636	High Similarity	NPC34421
0.8636	High Similarity	NPC114880
0.8636	High Similarity	NPC253201
0.8634	High Similarity	NPC475641
0.8634	High Similarity	NPC294512
0.8634	High Similarity	NPC475237
0.8618	High Similarity	NPC471001
0.8609	High Similarity	NPC286038
0.8608	High Similarity	NPC472773
0.8608	High Similarity	NPC469338
0.8608	High Similarity	NPC292389
0.8591	High Similarity	NPC243577
0.8581	High Similarity	NPC214541
0.8581	High Similarity	NPC44675
0.8581	High Similarity	NPC264943
0.8571	High Similarity	NPC472672
0.8571	High Similarity	NPC33938
0.8562	High Similarity	NPC170604
0.8562	High Similarity	NPC196846
0.8562	High Similarity	NPC215109
0.8562	High Similarity	NPC470997
0.8553	High Similarity	NPC19747
0.8553	High Similarity	NPC276551
0.8553	High Similarity	NPC27541
0.8553	High Similarity	NPC471007
0.8553	High Similarity	NPC62692
0.8553	High Similarity	NPC66991
0.8553	High Similarity	NPC126984
0.8553	High Similarity	NPC470940
0.8553	High Similarity	NPC61967
0.8553	High Similarity	NPC469849
0.8552	High Similarity	NPC476947
0.8552	High Similarity	NPC158525
0.8544	High Similarity	NPC200782
0.8544	High Similarity	NPC329938
0.8544	High Similarity	NPC82851
0.8544	High Similarity	NPC470792
0.8544	High Similarity	NPC472771
0.8543	High Similarity	NPC62799
0.8537	High Similarity	NPC472665
0.8509	High Similarity	NPC160651
0.85	High Similarity	NPC86800
0.85	High Similarity	NPC470875
0.8491	Intermediate Similarity	NPC477405
0.8485	Intermediate Similarity	NPC11062
0.8481	Intermediate Similarity	NPC472653
0.8481	Intermediate Similarity	NPC335761
0.8476	Intermediate Similarity	NPC56953
0.8476	Intermediate Similarity	NPC176413
0.8471	Intermediate Similarity	NPC472776
0.8471	Intermediate Similarity	NPC472778
0.8471	Intermediate Similarity	NPC472777
0.8471	Intermediate Similarity	NPC261597
0.8471	Intermediate Similarity	NPC197137
0.8471	Intermediate Similarity	NPC470118
0.8462	Intermediate Similarity	NPC75310
0.8457	Intermediate Similarity	NPC470995
0.8457	Intermediate Similarity	NPC88593
0.8457	Intermediate Similarity	NPC302392
0.8452	Intermediate Similarity	NPC48671
0.8452	Intermediate Similarity	NPC476201
0.8452	Intermediate Similarity	NPC470996
0.8452	Intermediate Similarity	NPC471002
0.8447	Intermediate Similarity	NPC472774
0.8447	Intermediate Similarity	NPC472775
0.8447	Intermediate Similarity	NPC173516
0.8447	Intermediate Similarity	NPC473766
0.8447	Intermediate Similarity	NPC473753
0.8447	Intermediate Similarity	NPC472282
0.8438	Intermediate Similarity	NPC472664
0.8438	Intermediate Similarity	NPC276735
0.8438	Intermediate Similarity	NPC470182
0.8431	Intermediate Similarity	NPC93666
0.8428	Intermediate Similarity	NPC263432
0.8428	Intermediate Similarity	NPC18347
0.8428	Intermediate Similarity	NPC149896
0.8428	Intermediate Similarity	NPC69028
0.8428	Intermediate Similarity	NPC5079
0.8421	Intermediate Similarity	NPC470999
0.8418	Intermediate Similarity	NPC307383
0.8418	Intermediate Similarity	NPC473368
0.8418	Intermediate Similarity	NPC472671
0.8414	Intermediate Similarity	NPC218838
0.8408	Intermediate Similarity	NPC107646
0.8403	Intermediate Similarity	NPC89133
0.84	Intermediate Similarity	NPC52412
0.8397	Intermediate Similarity	NPC282445
0.8397	Intermediate Similarity	NPC178932
0.8397	Intermediate Similarity	NPC44606
0.8397	Intermediate Similarity	NPC30222
0.8397	Intermediate Similarity	NPC10429
0.8395	Intermediate Similarity	NPC271235
0.8395	Intermediate Similarity	NPC471397
0.8392	Intermediate Similarity	NPC59502
0.8389	Intermediate Similarity	NPC56197
0.8387	Intermediate Similarity	NPC272590
0.8387	Intermediate Similarity	NPC18135
0.8385	Intermediate Similarity	NPC472141
0.8377	Intermediate Similarity	NPC472654
0.8377	Intermediate Similarity	NPC195325
0.8377	Intermediate Similarity	NPC470998
0.8375	Intermediate Similarity	NPC302369
0.8375	Intermediate Similarity	NPC469889
0.8375	Intermediate Similarity	NPC234660
0.8375	Intermediate Similarity	NPC51568
0.8375	Intermediate Similarity	NPC39986
0.8375	Intermediate Similarity	NPC134254
0.8366	Intermediate Similarity	NPC302987
0.8365	Intermediate Similarity	NPC25255
0.8365	Intermediate Similarity	NPC470789
0.8365	Intermediate Similarity	NPC477402
0.8355	Intermediate Similarity	NPC290038
0.8355	Intermediate Similarity	NPC34056
0.8354	Intermediate Similarity	NPC472772
0.8354	Intermediate Similarity	NPC475066
0.8354	Intermediate Similarity	NPC214495
0.8354	Intermediate Similarity	NPC249021
0.8354	Intermediate Similarity	NPC45101
0.8354	Intermediate Similarity	NPC470119
0.8354	Intermediate Similarity	NPC167142
0.8354	Intermediate Similarity	NPC36655
0.8354	Intermediate Similarity	NPC187149
0.8344	Intermediate Similarity	NPC35000
0.8344	Intermediate Similarity	NPC469336
0.8344	Intermediate Similarity	NPC476262
0.8344	Intermediate Similarity	NPC25351

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 NPC228842 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	834
0.2-0.3	1495
0.3-0.4	2515
0.4-0.5	2181
0.5-0.6	1223
0.6-0.7	509
0.7-0.8	93
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8443	Intermediate Similarity	NPD8434	Phase 2
0.84	Intermediate Similarity	NPD4628	Phase 3
0.8253	Intermediate Similarity	NPD6764	Approved
0.8253	Intermediate Similarity	NPD6765	Approved
0.8113	Intermediate Similarity	NPD5761	Phase 2
0.8113	Intermediate Similarity	NPD5760	Phase 2
0.8092	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD6784	Approved
0.8059	Intermediate Similarity	NPD6785	Approved
0.7961	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6599	Discontinued
0.7898	Intermediate Similarity	NPD6273	Approved
0.7862	Intermediate Similarity	NPD7458	Discontinued
0.7805	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7819	Suspended
0.7778	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD8127	Discontinued
0.7658	Intermediate Similarity	NPD6799	Approved
0.7658	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5844	Phase 1
0.764	Intermediate Similarity	NPD3226	Approved
0.7636	Intermediate Similarity	NPD3749	Approved
0.7636	Intermediate Similarity	NPD7075	Discontinued
0.7616	Intermediate Similarity	NPD6559	Discontinued
0.7603	Intermediate Similarity	NPD1608	Approved
0.7597	Intermediate Similarity	NPD2799	Discontinued
0.759	Intermediate Similarity	NPD919	Approved
0.758	Intermediate Similarity	NPD7003	Approved
0.758	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD3764	Approved
0.7546	Intermediate Similarity	NPD7411	Suspended
0.7543	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6355	Discontinued
0.7516	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD920	Approved
0.7515	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD8032	Phase 2
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD6801	Discontinued
0.75	Intermediate Similarity	NPD1471	Phase 3
0.7484	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7095	Approved
0.7483	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3882	Suspended
0.7468	Intermediate Similarity	NPD4110	Phase 3
0.7468	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3750	Approved
0.7468	Intermediate Similarity	NPD8166	Discontinued
0.7455	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5494	Approved
0.7436	Intermediate Similarity	NPD6100	Approved
0.7436	Intermediate Similarity	NPD6099	Approved
0.7434	Intermediate Similarity	NPD6798	Discontinued
0.7427	Intermediate Similarity	NPD7473	Discontinued
0.7423	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD17	Approved
0.7394	Intermediate Similarity	NPD1934	Approved
0.7391	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2344	Approved
0.7375	Intermediate Similarity	NPD7236	Approved
0.7372	Intermediate Similarity	NPD3748	Approved
0.7365	Intermediate Similarity	NPD3972	Approved
0.7353	Intermediate Similarity	NPD6232	Discontinued
0.7338	Intermediate Similarity	NPD4140	Approved
0.7325	Intermediate Similarity	NPD1551	Phase 2
0.7325	Intermediate Similarity	NPD2796	Approved
0.732	Intermediate Similarity	NPD3268	Approved
0.732	Intermediate Similarity	NPD2313	Discontinued
0.732	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2354	Approved
0.7306	Intermediate Similarity	NPD8404	Phase 2
0.7305	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD1243	Approved
0.7289	Intermediate Similarity	NPD37	Approved
0.7284	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2534	Approved
0.7284	Intermediate Similarity	NPD2532	Approved
0.7284	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2533	Approved
0.7283	Intermediate Similarity	NPD7177	Discontinued
0.7283	Intermediate Similarity	NPD3818	Discontinued
0.7279	Intermediate Similarity	NPD1778	Approved
0.7278	Intermediate Similarity	NPD5763	Approved
0.7278	Intermediate Similarity	NPD6234	Discontinued
0.7278	Intermediate Similarity	NPD5762	Approved
0.7273	Intermediate Similarity	NPD7028	Phase 2
0.7273	Intermediate Similarity	NPD4380	Phase 2
0.7267	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4965	Approved
0.7262	Intermediate Similarity	NPD4966	Approved
0.7262	Intermediate Similarity	NPD7768	Phase 2
0.7262	Intermediate Similarity	NPD4967	Phase 2
0.7261	Intermediate Similarity	NPD4308	Phase 3
0.7261	Intermediate Similarity	NPD7033	Discontinued
0.7246	Intermediate Similarity	NPD2801	Approved
0.7233	Intermediate Similarity	NPD1549	Phase 2
0.7233	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8313	Approved
0.7232	Intermediate Similarity	NPD8312	Approved
0.7226	Intermediate Similarity	NPD4060	Phase 1
0.7219	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2797	Approved
0.7205	Intermediate Similarity	NPD2309	Approved
0.7205	Intermediate Similarity	NPD3887	Approved
0.7195	Intermediate Similarity	NPD5403	Approved
0.7193	Intermediate Similarity	NPD1247	Approved
0.7184	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5401	Approved
0.7171	Intermediate Similarity	NPD2798	Approved
0.717	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6166	Phase 2
0.7161	Intermediate Similarity	NPD6233	Phase 2
0.7159	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1510	Phase 2
0.7152	Intermediate Similarity	NPD7239	Suspended
0.7152	Intermediate Similarity	NPD1283	Approved
0.7151	Intermediate Similarity	NPD7229	Phase 3
0.7151	Intermediate Similarity	NPD4107	Approved
0.7143	Intermediate Similarity	NPD9545	Approved
0.7143	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1465	Phase 2
0.7134	Intermediate Similarity	NPD5049	Phase 3
0.7128	Intermediate Similarity	NPD7497	Discontinued
0.7127	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD9494	Approved
0.7117	Intermediate Similarity	NPD1511	Approved
0.7115	Intermediate Similarity	NPD4307	Phase 2
0.711	Intermediate Similarity	NPD3926	Phase 2
0.7107	Intermediate Similarity	NPD2935	Discontinued
0.7105	Intermediate Similarity	NPD3266	Approved
0.7105	Intermediate Similarity	NPD3267	Approved
0.7101	Intermediate Similarity	NPD5402	Approved
0.7093	Intermediate Similarity	NPD6959	Discontinued
0.7089	Intermediate Similarity	NPD7097	Phase 1
0.7086	Intermediate Similarity	NPD7799	Discontinued
0.7081	Intermediate Similarity	NPD2800	Approved
0.7078	Intermediate Similarity	NPD6832	Phase 2
0.7074	Intermediate Similarity	NPD3057	Approved
0.707	Intermediate Similarity	NPD5735	Approved
0.7069	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2353	Approved
0.7063	Intermediate Similarity	NPD6005	Phase 3
0.7063	Intermediate Similarity	NPD6004	Phase 3
0.7063	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6002	Phase 3
0.7063	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD8455	Phase 2
0.7039	Intermediate Similarity	NPD1876	Approved
0.703	Intermediate Similarity	NPD1512	Approved
0.7025	Intermediate Similarity	NPD1607	Approved
0.7022	Intermediate Similarity	NPD7685	Pre-registration
0.7021	Intermediate Similarity	NPD4482	Phase 3
0.7019	Intermediate Similarity	NPD4534	Discontinued
0.7017	Intermediate Similarity	NPD8150	Discontinued
0.7006	Intermediate Similarity	NPD1240	Approved
0.7006	Intermediate Similarity	NPD7074	Phase 3
0.7006	Intermediate Similarity	NPD2979	Phase 3
0.7	Intermediate Similarity	NPD4477	Approved
0.7	Intermediate Similarity	NPD2438	Suspended
0.7	Intermediate Similarity	NPD4476	Approved
0.6994	Remote Similarity	NPD6190	Approved
0.6993	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD3751	Discontinued
0.6989	Remote Similarity	NPD7228	Approved
0.6984	Remote Similarity	NPD3533	Approved
0.6984	Remote Similarity	NPD2972	Approved
0.698	Remote Similarity	NPD5585	Approved
0.6962	Remote Similarity	NPD447	Suspended
0.6962	Remote Similarity	NPD230	Phase 1
0.6962	Remote Similarity	NPD1933	Approved
0.6954	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3787	Discontinued
0.6954	Remote Similarity	NPD1281	Approved
0.6949	Remote Similarity	NPD7054	Approved
0.6949	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5647	Approved
0.6943	Remote Similarity	NPD6663	Approved
0.6943	Remote Similarity	NPD4062	Phase 3
0.6939	Remote Similarity	NPD4198	Discontinued
0.6928	Remote Similarity	NPD8651	Approved
0.6928	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6386	Approved
0.6923	Remote Similarity	NPD6677	Suspended
0.6923	Remote Similarity	NPD6385	Approved
0.6918	Remote Similarity	NPD1241	Discontinued
0.6914	Remote Similarity	NPD5958	Discontinued
0.691	Remote Similarity	NPD7472	Approved
0.6908	Remote Similarity	NPD9717	Approved
0.6906	Remote Similarity	NPD8407	Phase 2
0.6903	Remote Similarity	NPD5736	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