NPASS Compound

Structure

NPC205316 OpenBabel07101718202D 26 31 0 0 1 0 0 0 0 0999 V2000 -5.8448 -1.1121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8448 -2.8442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7570 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3958 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1860 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3448 -1.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3448 -1.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8060 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9836 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5768 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2079 -2.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9781 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3200 1.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7570 -2.7872 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 1 10 2 0 0 0 0 2 10 1 0 0 0 0 3 11 2 0 0 0 0 3 13 1 0 0 0 0 4 11 1 0 0 0 0 4 15 1 0 0 0 0 5 12 2 0 0 0 0 5 19 1 0 0 0 0 6 16 2 0 0 0 0 6 17 1 0 0 0 0 7 18 2 0 0 0 0 7 20 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 9 24 1 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 17 2 0 0 0 0 14 8 1 6 0 0 0 14 21 1 0 0 0 0 15 10 1 1 0 0 0 15 25 1 0 0 0 0 16 25 1 0 0 0 0 17 22 1 0 0 0 0 18 26 1 0 0 0 0 19 20 2 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 21 13 1 6 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.12
Volume:	345.929
LogP:	5.411
LogD:	3.722
LogS:	-7.28
# Rotatable Bonds:	1
TPSA:	46.15
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.73
Synthetic Accessibility Score:	3.948
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.017
MDCK Permeability:	2.3997819880605675e-05
Pgp-inhibitor:	0.055
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	99.16942596435547%
Volume Distribution (VD):	0.849
Pgp-substrate:	1.5175033807754517%

ADMET: Metabolism

CYP1A2-inhibitor:	0.354
CYP1A2-substrate:	0.85
CYP2C19-inhibitor:	0.963
CYP2C19-substrate:	0.563
CYP2C9-inhibitor:	0.887
CYP2C9-substrate:	0.871
CYP2D6-inhibitor:	0.8
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.946
CYP3A4-substrate:	0.721

ADMET: Excretion

Clearance (CL):	12.578
Half-life (T1/2):	0.114

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.948
Drug-inuced Liver Injury (DILI):	0.939
AMES Toxicity:	0.921
Rat Oral Acute Toxicity:	0.556
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.142
Carcinogencity:	0.623
Eye Corrosion:	0.003
Eye Irritation:	0.423
Respiratory Toxicity:	0.618

Download Data

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

Natural Product: NPC205316

Natural Product ID:	NPC205316
*Common Name:**	Emoroidocarpan
IUPAC Name:	n.a.
Synonyms:	Emoroidocarpan
Standard InCHIKey:	JDLWWTGCAJYSSZ-ZSDSOXJFSA-N
Standard InCHI:	InChI=1S/C21H18O5/c1-10(2)15-4-11-3-13-17(6-16(11)25-15)22-8-14-12-5-19-20(24-9-23-19)7-18(12)26-21(13)14/h3,5-7,14-15,21H,1,4,8-9H2,2H3/t14-,15+,21-/m0/s1
SMILES:	CC(=C)[C@H]1Cc2c(O1)cc1c(c2)[C@@H]2Oc3c([C@@H]2CO1)cc1c(c3)OCO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224761
PubChem CID:	46939886
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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
NPO6364	Pongamiopsis pervilleana	Species	Fabaceae	Eukaryota	n.a.	Madagascar Dry Forest	n.a.	PMID[20804165]
NPO6364	Pongamiopsis pervilleana	Species	Fabaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	26500.0	nM	PMID[566060]

☑ 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 NPC205316 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	552
0.1-0.2	1742
0.2-0.3	4834
0.3-0.4	11985
0.4-0.5	6279
0.5-0.6	4813
0.6-0.7	8289
0.7-0.8	3282
0.8-0.85	711
0.85-0.9	180
0.9-0.95	23
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9638	High Similarity	NPC472562
0.9638	High Similarity	NPC80326
0.9577	High Similarity	NPC240521
0.9565	High Similarity	NPC300798
0.9565	High Similarity	NPC58137
0.9507	High Similarity	NPC71726
0.9496	High Similarity	NPC174522
0.9275	High Similarity	NPC78047
0.927	High Similarity	NPC31530
0.922	High Similarity	NPC311057
0.9203	High Similarity	NPC189474
0.9203	High Similarity	NPC148893
0.9203	High Similarity	NPC49235
0.9203	High Similarity	NPC25333
0.9161	High Similarity	NPC42716
0.9161	High Similarity	NPC180953
0.9161	High Similarity	NPC11422
0.9161	High Similarity	NPC474749
0.9161	High Similarity	NPC178014
0.9149	High Similarity	NPC312199
0.913	High Similarity	NPC170779
0.913	High Similarity	NPC474478
0.913	High Similarity	NPC90083
0.9124	High Similarity	NPC261812
0.9124	High Similarity	NPC65183
0.9124	High Similarity	NPC72046
0.9122	High Similarity	NPC159922
0.9103	High Similarity	NPC166584
0.9103	High Similarity	NPC301961
0.9097	High Similarity	NPC162193
0.9097	High Similarity	NPC226540
0.9085	High Similarity	NPC474295
0.9058	High Similarity	NPC266848
0.9058	High Similarity	NPC136750
0.9028	High Similarity	NPC307466
0.9007	High Similarity	NPC113550
0.8986	High Similarity	NPC7744
0.898	High Similarity	NPC238140
0.8973	High Similarity	NPC270751
0.8944	High Similarity	NPC216434
0.8944	High Similarity	NPC103448
0.8944	High Similarity	NPC46591
0.8929	High Similarity	NPC474139
0.8913	High Similarity	NPC227160
0.8913	High Similarity	NPC82111
0.8913	High Similarity	NPC192255
0.8904	High Similarity	NPC116019
0.8889	High Similarity	NPC102044
0.8889	High Similarity	NPC85264
0.8889	High Similarity	NPC47633
0.8889	High Similarity	NPC474808
0.8873	High Similarity	NPC9068
0.8865	High Similarity	NPC121651
0.8851	High Similarity	NPC472710
0.8851	High Similarity	NPC472709
0.8841	High Similarity	NPC237169
0.8841	High Similarity	NPC271208
0.8841	High Similarity	NPC470624
0.8841	High Similarity	NPC233224
0.8828	High Similarity	NPC280092
0.8828	High Similarity	NPC63879
0.8828	High Similarity	NPC12641
0.8828	High Similarity	NPC93323
0.8828	High Similarity	NPC45257
0.8811	High Similarity	NPC226547
0.8811	High Similarity	NPC56091
0.8811	High Similarity	NPC27495
0.8803	High Similarity	NPC196420
0.8759	High Similarity	NPC255566
0.8759	High Similarity	NPC473092
0.8759	High Similarity	NPC298317
0.8759	High Similarity	NPC12728
0.8759	High Similarity	NPC473093
0.8759	High Similarity	NPC8050
0.8759	High Similarity	NPC185071
0.875	High Similarity	NPC247291
0.8741	High Similarity	NPC292487
0.8733	High Similarity	NPC302610
0.8732	High Similarity	NPC32189
0.8732	High Similarity	NPC11453
0.8732	High Similarity	NPC197166
0.8716	High Similarity	NPC248132
0.8716	High Similarity	NPC130449
0.8714	High Similarity	NPC158526
0.8714	High Similarity	NPC129687
0.8714	High Similarity	NPC33611
0.8714	High Similarity	NPC171928
0.8714	High Similarity	NPC16830
0.8714	High Similarity	NPC100223
0.8707	High Similarity	NPC33832
0.8699	High Similarity	NPC217635
0.8699	High Similarity	NPC79429
0.8699	High Similarity	NPC477701
0.8699	High Similarity	NPC166884
0.8699	High Similarity	NPC471667
0.8699	High Similarity	NPC141569
0.8696	High Similarity	NPC31707
0.8696	High Similarity	NPC222127
0.8696	High Similarity	NPC57119
0.8696	High Similarity	NPC158471
0.8696	High Similarity	NPC226862
0.8696	High Similarity	NPC328682
0.8696	High Similarity	NPC82862
0.8696	High Similarity	NPC54321
0.8696	High Similarity	NPC281864
0.8696	High Similarity	NPC165128
0.869	High Similarity	NPC107161
0.8681	High Similarity	NPC177868
0.8681	High Similarity	NPC259519
0.8671	High Similarity	NPC283949
0.8671	High Similarity	NPC185908
0.8671	High Similarity	NPC477938
0.8662	High Similarity	NPC150534
0.8658	High Similarity	NPC55158
0.8658	High Similarity	NPC35877
0.8658	High Similarity	NPC95392
0.8658	High Similarity	NPC51328
0.8658	High Similarity	NPC55715
0.8658	High Similarity	NPC286235
0.8652	High Similarity	NPC1474
0.8649	High Similarity	NPC16269
0.8649	High Similarity	NPC21776
0.8649	High Similarity	NPC101376
0.8639	High Similarity	NPC476301
0.8639	High Similarity	NPC43508
0.863	High Similarity	NPC81638
0.8623	High Similarity	NPC98745
0.8611	High Similarity	NPC471388
0.8611	High Similarity	NPC30951
0.8611	High Similarity	NPC6369
0.8601	High Similarity	NPC173660
0.86	High Similarity	NPC98624
0.8592	High Similarity	NPC185680
0.8592	High Similarity	NPC47181
0.8592	High Similarity	NPC256776
0.8592	High Similarity	NPC145722
0.8591	High Similarity	NPC175976
0.8571	High Similarity	NPC239254
0.8571	High Similarity	NPC172171
0.8562	High Similarity	NPC287124
0.8562	High Similarity	NPC42871
0.8562	High Similarity	NPC41782
0.8562	High Similarity	NPC246947
0.8562	High Similarity	NPC164152
0.8562	High Similarity	NPC188962
0.8562	High Similarity	NPC202249
0.8552	High Similarity	NPC184797
0.8552	High Similarity	NPC160283
0.8552	High Similarity	NPC284464
0.8552	High Similarity	NPC254759
0.8552	High Similarity	NPC309124
0.8551	High Similarity	NPC9891
0.8551	High Similarity	NPC112571
0.8551	High Similarity	NPC285725
0.8551	High Similarity	NPC186845
0.8551	High Similarity	NPC50683
0.8551	High Similarity	NPC88297
0.8531	High Similarity	NPC18576
0.8531	High Similarity	NPC195022
0.8523	High Similarity	NPC15956
0.8523	High Similarity	NPC275284
0.8523	High Similarity	NPC227902
0.8523	High Similarity	NPC114505
0.8523	High Similarity	NPC224674
0.8523	High Similarity	NPC213074
0.8523	High Similarity	NPC193473
0.8523	High Similarity	NPC39657
0.8523	High Similarity	NPC31325
0.8521	High Similarity	NPC196937
0.8514	High Similarity	NPC475868
0.8514	High Similarity	NPC469557
0.8511	High Similarity	NPC469698
0.8511	High Similarity	NPC473412
0.8506	High Similarity	NPC189730
0.8503	High Similarity	NPC218510
0.8503	High Similarity	NPC76415
0.8503	High Similarity	NPC265154
0.8493	Intermediate Similarity	NPC471389
0.8493	Intermediate Similarity	NPC87725
0.8493	Intermediate Similarity	NPC471908
0.8493	Intermediate Similarity	NPC311530
0.8493	Intermediate Similarity	NPC263261
0.8489	Intermediate Similarity	NPC158737
0.8483	Intermediate Similarity	NPC25966
0.8483	Intermediate Similarity	NPC70682
0.8483	Intermediate Similarity	NPC193666
0.8483	Intermediate Similarity	NPC292882
0.8483	Intermediate Similarity	NPC123526
0.8483	Intermediate Similarity	NPC236306
0.8483	Intermediate Similarity	NPC232164
0.8483	Intermediate Similarity	NPC319647
0.8483	Intermediate Similarity	NPC245207
0.8483	Intermediate Similarity	NPC127218
0.8483	Intermediate Similarity	NPC473739
0.8483	Intermediate Similarity	NPC260741
0.8483	Intermediate Similarity	NPC88640
0.8472	Intermediate Similarity	NPC172818
0.8472	Intermediate Similarity	NPC143895
0.8472	Intermediate Similarity	NPC25695
0.8462	Intermediate Similarity	NPC16485

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 NPC205316 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	446
0.1-0.2	927
0.2-0.3	2074
0.3-0.4	2730
0.4-0.5	1542
0.5-0.6	846
0.6-0.7	522
0.7-0.8	59
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8153	Intermediate Similarity	NPD4967	Phase 2
0.8153	Intermediate Similarity	NPD4965	Approved
0.8153	Intermediate Similarity	NPD4966	Approved
0.8058	Intermediate Similarity	NPD3705	Approved
0.805	Intermediate Similarity	NPD6234	Discontinued
0.8	Intermediate Similarity	NPD5494	Approved
0.8	Intermediate Similarity	NPD6674	Discontinued
0.7962	Intermediate Similarity	NPD37	Approved
0.7945	Intermediate Similarity	NPD1613	Approved
0.7945	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD7199	Phase 2
0.7818	Intermediate Similarity	NPD7228	Approved
0.7808	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3027	Phase 3
0.7724	Intermediate Similarity	NPD2861	Phase 2
0.7707	Intermediate Similarity	NPD1653	Approved
0.7671	Intermediate Similarity	NPD4908	Phase 1
0.7633	Intermediate Similarity	NPD7240	Approved
0.7552	Intermediate Similarity	NPD1610	Phase 2
0.7536	Intermediate Similarity	NPD5283	Phase 1
0.7516	Intermediate Similarity	NPD3382	Approved
0.7516	Intermediate Similarity	NPD3383	Approved
0.7516	Intermediate Similarity	NPD3384	Approved
0.7483	Intermediate Similarity	NPD3018	Phase 2
0.7456	Intermediate Similarity	NPD5844	Phase 1
0.7421	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD3818	Discontinued
0.7389	Intermediate Similarity	NPD5058	Phase 3
0.7383	Intermediate Similarity	NPD4625	Phase 3
0.7379	Intermediate Similarity	NPD2981	Phase 2
0.7362	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2983	Phase 2
0.7329	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2982	Phase 2
0.7329	Intermediate Similarity	NPD4749	Approved
0.7325	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1091	Approved
0.731	Intermediate Similarity	NPD7074	Phase 3
0.7308	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1934	Approved
0.7251	Intermediate Similarity	NPD7054	Approved
0.7233	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6559	Discontinued
0.7215	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7472	Approved
0.7184	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1548	Phase 1
0.7152	Intermediate Similarity	NPD2801	Approved
0.7152	Intermediate Similarity	NPD7466	Approved
0.7126	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4060	Phase 1
0.7115	Intermediate Similarity	NPD3454	Phase 3
0.7108	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3817	Phase 2
0.7103	Intermediate Similarity	NPD1357	Approved
0.7102	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1247	Approved
0.7086	Intermediate Similarity	NPD7808	Phase 3
0.7086	Intermediate Similarity	NPD7549	Discontinued
0.7078	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5124	Phase 1
0.707	Intermediate Similarity	NPD1375	Discontinued
0.7069	Intermediate Similarity	NPD6797	Phase 2
0.7062	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5588	Approved
0.7051	Intermediate Similarity	NPD4108	Discontinued
0.7048	Intermediate Similarity	NPD8455	Phase 2
0.7047	Intermediate Similarity	NPD8651	Approved
0.7044	Intermediate Similarity	NPD6331	Phase 2
0.7043	Intermediate Similarity	NPD7680	Approved
0.7029	Intermediate Similarity	NPD7251	Discontinued
0.7024	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3539	Phase 1
0.6993	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4538	Approved
0.6987	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4536	Approved
0.6982	Remote Similarity	NPD919	Approved
0.698	Remote Similarity	NPD5327	Phase 3
0.6977	Remote Similarity	NPD6166	Phase 2
0.6977	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3657	Discovery
0.6964	Remote Similarity	NPD3882	Suspended
0.6962	Remote Similarity	NPD3540	Phase 1
0.6962	Remote Similarity	NPD7266	Discontinued
0.6959	Remote Similarity	NPD1611	Approved
0.6959	Remote Similarity	NPD7229	Phase 3
0.6959	Remote Similarity	NPD3787	Discontinued
0.6957	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7124	Phase 2
0.6954	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7819	Suspended
0.6946	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5125	Phase 3
0.6939	Remote Similarity	NPD5126	Approved
0.6933	Remote Similarity	NPD6696	Suspended
0.6933	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3620	Phase 2
0.6903	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2796	Approved
0.689	Remote Similarity	NPD5976	Discontinued
0.6879	Remote Similarity	NPD7097	Phase 1
0.6879	Remote Similarity	NPD6111	Discontinued
0.6879	Remote Similarity	NPD4481	Phase 3
0.6875	Remote Similarity	NPD1652	Phase 2
0.686	Remote Similarity	NPD6232	Discontinued
0.6859	Remote Similarity	NPD5735	Approved
0.6859	Remote Similarity	NPD6355	Discontinued
0.6859	Remote Similarity	NPD1933	Approved
0.6855	Remote Similarity	NPD5762	Approved
0.6855	Remote Similarity	NPD5763	Approved
0.6848	Remote Similarity	NPD4210	Discontinued
0.6839	Remote Similarity	NPD7473	Discontinued
0.6835	Remote Similarity	NPD5960	Phase 3
0.6832	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3892	Phase 2
0.6832	Remote Similarity	NPD4110	Phase 3
0.6832	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6671	Approved
0.6824	Remote Similarity	NPD7075	Discontinued
0.6821	Remote Similarity	NPD3926	Phase 2
0.6809	Remote Similarity	NPD5006	Approved
0.6809	Remote Similarity	NPD5005	Approved
0.6807	Remote Similarity	NPD4005	Discontinued
0.6805	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6842	Approved
0.6796	Remote Similarity	NPD6841	Approved
0.6796	Remote Similarity	NPD6843	Phase 3
0.6792	Remote Similarity	NPD6100	Approved
0.6792	Remote Similarity	NPD6099	Approved
0.6772	Remote Similarity	NPD7119	Phase 2
0.677	Remote Similarity	NPD5177	Phase 3
0.6768	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD4380	Phase 2
0.6766	Remote Similarity	NPD4678	Approved
0.6766	Remote Similarity	NPD4675	Approved
0.6766	Remote Similarity	NPD7028	Phase 2
0.6763	Remote Similarity	NPD3051	Approved
0.6761	Remote Similarity	NPD8156	Discontinued
0.6757	Remote Similarity	NPD5691	Approved
0.6755	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6002	Phase 3
0.675	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6004	Phase 3
0.675	Remote Similarity	NPD6005	Phase 3
0.6746	Remote Similarity	NPD1465	Phase 2
0.6744	Remote Similarity	NPD5677	Discontinued
0.6736	Remote Similarity	NPD5535	Approved
0.6735	Remote Similarity	NPD5536	Phase 2
0.6731	Remote Similarity	NPD6233	Phase 2
0.673	Remote Similarity	NPD3748	Approved
0.6728	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD2969	Approved
0.6724	Remote Similarity	NPD2970	Approved
0.6712	Remote Similarity	NPD6387	Discontinued
0.6712	Remote Similarity	NPD7157	Approved
0.6708	Remote Similarity	NPD2424	Discontinued
0.6707	Remote Similarity	NPD1511	Approved
0.6707	Remote Similarity	NPD7212	Phase 2
0.6707	Remote Similarity	NPD7213	Phase 3
0.6706	Remote Similarity	NPD5402	Approved
0.6705	Remote Similarity	NPD8251	Approved
0.6705	Remote Similarity	NPD8099	Discontinued
0.6705	Remote Similarity	NPD8127	Discontinued
0.6705	Remote Similarity	NPD3751	Discontinued
0.6705	Remote Similarity	NPD6959	Discontinued
0.6705	Remote Similarity	NPD8252	Approved
0.6703	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2684	Approved
0.6688	Remote Similarity	NPD4140	Approved
0.6687	Remote Similarity	NPD2438	Suspended
0.6687	Remote Similarity	NPD2161	Phase 2
0.6686	Remote Similarity	NPD6801	Discontinued
0.6685	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4420	Approved
0.6667	Remote Similarity	NPD3496	Discontinued
0.6667	Remote Similarity	NPD5111	Phase 2
0.6667	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4236	Phase 3
0.6667	Remote Similarity	NPD5109	Approved
0.6667	Remote Similarity	NPD5110	Phase 2
0.6667	Remote Similarity	NPD1139	Approved
0.6667	Remote Similarity	NPD4237	Approved
0.6667	Remote Similarity	NPD2200	Suspended

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