NPASS Compound

Structure

NPC274640 OpenBabel07101718292D 25 27 0 0 0 0 0 0 0 0999 V2000 0.4666 6.0577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4469 5.6509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1646 0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2093 4.5677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1810 3.3406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2257 4.2541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 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 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8080 3.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3621 5.0632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2202 4.3587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3566 4.9586 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1701 0.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8025 3.6542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 13 2 0 0 0 0 8 15 2 0 0 0 0 9 10 2 0 0 0 0 9 12 1 0 0 0 0 10 20 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 17 2 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 19 1 0 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 18 21 1 0 0 0 0 19 22 2 0 0 0 0 19 25 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	652.27
Volume:	632.41
LogP:	1.925
LogD:	1.062
LogS:	-4.457
# Rotatable Bonds:	13
TPSA:	187.26
# H-Bond Aceptor:	14
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.238
Synthetic Accessibility Score:	5.349
Fsp3:	0.75
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.373
MDCK Permeability:	0.0002118608681485057
Pgp-inhibitor:	0.995
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.923
20% Bioavailability (F20%):	0.368
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.141
Plasma Protein Binding (PPB):	34.142189025878906%
Volume Distribution (VD):	1.457
Pgp-substrate:	27.467514038085938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.012
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.087
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.424
CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.245
CYP3A4-substrate:	0.508

ADMET: Excretion

Clearance (CL):	2.668
Half-life (T1/2):	0.285

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.98
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.109
Rat Oral Acute Toxicity:	0.067
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.147
Carcinogencity:	0.028
Eye Corrosion:	0.004
Eye Irritation:	0.026
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC274640

Natural Product ID:	NPC274640
*Common Name:**	Clausamine E
IUPAC Name:	methyl 4-[(E)-3-hydroxy-3-methylbut-1-enyl]-1-methoxy-9H-carbazole-3-carboxylate
Synonyms:	Clausamine E
Standard InCHIKey:	GOGHABCCDYNZSW-MDZDMXLPSA-N
Standard InCHI:	InChI=1S/C20H21NO4/c1-20(2,23)10-9-12-14(19(22)25-4)11-16(24-3)18-17(12)13-7-5-6-8-15(13)21-18/h5-11,21,23H,1-4H3/b10-9+
SMILES:	COC(=O)c1cc(OC)c2c(c1/C=C/C(O)(C)C)c1ccccc1[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1088635
PubChem CID:	10759519
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1080/10412905.1999.9701119]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1080/10412905.1999.9701119]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650093]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19459693]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	leaf oil	n.a.	n.a.	PMID[22472691]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	47.3	%	PMID[521441]

☑ 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 NPC274640 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	413
0.1-0.2	2536
0.2-0.3	10912
0.3-0.4	6139
0.4-0.5	15224
0.5-0.6	5163
0.6-0.7	1776
0.7-0.8	480
0.8-0.85	33
0.85-0.9	11
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9752	High Similarity	NPC144452
0.9512	High Similarity	NPC51388
0.9458	High Similarity	NPC184408
0.9437	High Similarity	NPC475844
0.9426	High Similarity	NPC474688
0.9366	High Similarity	NPC225279
0.9356	High Similarity	NPC39500
0.9151	High Similarity	NPC474701
0.9122	High Similarity	NPC118228
0.8976	High Similarity	NPC187501
0.8947	High Similarity	NPC208084
0.8942	High Similarity	NPC293151
0.8915	High Similarity	NPC179287
0.8792	High Similarity	NPC87413
0.8774	High Similarity	NPC280799
0.8732	High Similarity	NPC300156
0.8689	High Similarity	NPC4687
0.8558	High Similarity	NPC39679
0.8551	High Similarity	NPC174760
0.851	High Similarity	NPC283117
0.8498	Intermediate Similarity	NPC169402
0.8462	Intermediate Similarity	NPC45190
0.8439	Intermediate Similarity	NPC128823
0.8436	Intermediate Similarity	NPC294375
0.8423	Intermediate Similarity	NPC39370
0.8421	Intermediate Similarity	NPC249583
0.8421	Intermediate Similarity	NPC321428
0.8404	Intermediate Similarity	NPC116238
0.838	Intermediate Similarity	NPC150239
0.8349	Intermediate Similarity	NPC9894
0.8348	Intermediate Similarity	NPC6786
0.8333	Intermediate Similarity	NPC473186
0.8302	Intermediate Similarity	NPC199667
0.8287	Intermediate Similarity	NPC247803
0.8279	Intermediate Similarity	NPC3207
0.8267	Intermediate Similarity	NPC242928
0.8255	Intermediate Similarity	NPC473181
0.8224	Intermediate Similarity	NPC308137
0.8224	Intermediate Similarity	NPC310211
0.8203	Intermediate Similarity	NPC46561
0.819	Intermediate Similarity	NPC470018
0.8174	Intermediate Similarity	NPC198503
0.8168	Intermediate Similarity	NPC160381
0.813	Intermediate Similarity	NPC208522
0.8107	Intermediate Similarity	NPC475190
0.8089	Intermediate Similarity	NPC49547
0.8075	Intermediate Similarity	NPC193777
0.8056	Intermediate Similarity	NPC473180
0.8009	Intermediate Similarity	NPC23294
0.8	Intermediate Similarity	NPC473179
0.7991	Intermediate Similarity	NPC74575
0.7981	Intermediate Similarity	NPC470930
0.797	Intermediate Similarity	NPC474798
0.7963	Intermediate Similarity	NPC303951
0.7917	Intermediate Similarity	NPC209769
0.7905	Intermediate Similarity	NPC70956
0.7905	Intermediate Similarity	NPC243834
0.7895	Intermediate Similarity	NPC473182
0.789	Intermediate Similarity	NPC48353
0.7883	Intermediate Similarity	NPC132642
0.7881	Intermediate Similarity	NPC473188
0.7875	Intermediate Similarity	NPC89549
0.787	Intermediate Similarity	NPC86834
0.787	Intermediate Similarity	NPC210828
0.7867	Intermediate Similarity	NPC202503
0.7826	Intermediate Similarity	NPC473187
0.7826	Intermediate Similarity	NPC470017
0.7808	Intermediate Similarity	NPC94157
0.7792	Intermediate Similarity	NPC15801
0.7762	Intermediate Similarity	NPC230403
0.7758	Intermediate Similarity	NPC288987
0.7753	Intermediate Similarity	NPC473185
0.7752	Intermediate Similarity	NPC201697
0.7748	Intermediate Similarity	NPC314552
0.7725	Intermediate Similarity	NPC131017
0.7721	Intermediate Similarity	NPC291535
0.7721	Intermediate Similarity	NPC475112
0.7721	Intermediate Similarity	NPC475085
0.7719	Intermediate Similarity	NPC194740
0.7713	Intermediate Similarity	NPC473041
0.7713	Intermediate Similarity	NPC96321
0.77	Intermediate Similarity	NPC72211
0.7696	Intermediate Similarity	NPC476106
0.7685	Intermediate Similarity	NPC162484
0.7668	Intermediate Similarity	NPC312645
0.7657	Intermediate Similarity	NPC67401
0.7656	Intermediate Similarity	NPC246700
0.7653	Intermediate Similarity	NPC153042
0.7642	Intermediate Similarity	NPC252251
0.7639	Intermediate Similarity	NPC470022
0.7636	Intermediate Similarity	NPC470020
0.7633	Intermediate Similarity	NPC132385
0.7615	Intermediate Similarity	NPC165964
0.7613	Intermediate Similarity	NPC89508
0.7606	Intermediate Similarity	NPC70259
0.7591	Intermediate Similarity	NPC325297
0.7576	Intermediate Similarity	NPC260434
0.7576	Intermediate Similarity	NPC477531
0.7573	Intermediate Similarity	NPC270515
0.7569	Intermediate Similarity	NPC132539
0.7559	Intermediate Similarity	NPC205934
0.7559	Intermediate Similarity	NPC43787
0.7557	Intermediate Similarity	NPC471304
0.7556	Intermediate Similarity	NPC303658
0.7545	Intermediate Similarity	NPC148183
0.7545	Intermediate Similarity	NPC152768
0.7543	Intermediate Similarity	NPC475720
0.7543	Intermediate Similarity	NPC132329
0.7543	Intermediate Similarity	NPC474192
0.7542	Intermediate Similarity	NPC148889
0.7535	Intermediate Similarity	NPC306376
0.7532	Intermediate Similarity	NPC209174
0.7523	Intermediate Similarity	NPC223427
0.7522	Intermediate Similarity	NPC257851
0.7522	Intermediate Similarity	NPC478078
0.7512	Intermediate Similarity	NPC267423
0.7511	Intermediate Similarity	NPC329631
0.7511	Intermediate Similarity	NPC21638
0.751	Intermediate Similarity	NPC191489
0.75	Intermediate Similarity	NPC280714
0.75	Intermediate Similarity	NPC475253
0.7489	Intermediate Similarity	NPC311906
0.7489	Intermediate Similarity	NPC473183
0.7489	Intermediate Similarity	NPC38237
0.7489	Intermediate Similarity	NPC474428
0.7488	Intermediate Similarity	NPC141454
0.7488	Intermediate Similarity	NPC128751
0.7479	Intermediate Similarity	NPC473184
0.7478	Intermediate Similarity	NPC174576
0.7477	Intermediate Similarity	NPC276517
0.7467	Intermediate Similarity	NPC469928
0.7467	Intermediate Similarity	NPC330009
0.7459	Intermediate Similarity	NPC478083
0.7459	Intermediate Similarity	NPC472589
0.7456	Intermediate Similarity	NPC60621
0.7453	Intermediate Similarity	NPC144381
0.7453	Intermediate Similarity	NPC469497
0.7453	Intermediate Similarity	NPC106833
0.7449	Intermediate Similarity	NPC472588
0.7444	Intermediate Similarity	NPC220337
0.7444	Intermediate Similarity	NPC146418
0.7444	Intermediate Similarity	NPC208284
0.7443	Intermediate Similarity	NPC165599
0.7443	Intermediate Similarity	NPC476098
0.744	Intermediate Similarity	NPC88363
0.7438	Intermediate Similarity	NPC473800
0.7436	Intermediate Similarity	NPC473105
0.7429	Intermediate Similarity	NPC94943
0.7427	Intermediate Similarity	NPC84347
0.7426	Intermediate Similarity	NPC41501
0.7426	Intermediate Similarity	NPC475816
0.7412	Intermediate Similarity	NPC472099
0.7412	Intermediate Similarity	NPC323969
0.7403	Intermediate Similarity	NPC200888
0.7401	Intermediate Similarity	NPC131885
0.7397	Intermediate Similarity	NPC199277
0.7397	Intermediate Similarity	NPC135887
0.7393	Intermediate Similarity	NPC194040
0.7391	Intermediate Similarity	NPC205372
0.739	Intermediate Similarity	NPC315634
0.739	Intermediate Similarity	NPC100734
0.739	Intermediate Similarity	NPC88923
0.7389	Intermediate Similarity	NPC74969
0.7389	Intermediate Similarity	NPC36405
0.7381	Intermediate Similarity	NPC190007
0.738	Intermediate Similarity	NPC477532
0.7378	Intermediate Similarity	NPC324361
0.7378	Intermediate Similarity	NPC476287
0.7375	Intermediate Similarity	NPC160898
0.7371	Intermediate Similarity	NPC157931
0.7368	Intermediate Similarity	NPC74360
0.7364	Intermediate Similarity	NPC475774
0.7364	Intermediate Similarity	NPC134848
0.7358	Intermediate Similarity	NPC207620
0.7352	Intermediate Similarity	NPC476044
0.7342	Intermediate Similarity	NPC244741
0.7339	Intermediate Similarity	NPC471762
0.7333	Intermediate Similarity	NPC142385
0.7333	Intermediate Similarity	NPC176127
0.7333	Intermediate Similarity	NPC212535
0.7331	Intermediate Similarity	NPC169716
0.7331	Intermediate Similarity	NPC253675
0.7328	Intermediate Similarity	NPC284685
0.7317	Intermediate Similarity	NPC53534
0.7316	Intermediate Similarity	NPC94842
0.7316	Intermediate Similarity	NPC314633
0.7306	Intermediate Similarity	NPC213308
0.7301	Intermediate Similarity	NPC232225
0.7299	Intermediate Similarity	NPC84478
0.7292	Intermediate Similarity	NPC473540
0.729	Intermediate Similarity	NPC83111
0.7285	Intermediate Similarity	NPC476138
0.7285	Intermediate Similarity	NPC245816
0.7281	Intermediate Similarity	NPC305984
0.728	Intermediate Similarity	NPC152620
0.7277	Intermediate Similarity	NPC284102
0.7273	Intermediate Similarity	NPC475666
0.7273	Intermediate Similarity	NPC58209
0.7269	Intermediate Similarity	NPC477979
0.7266	Intermediate Similarity	NPC195788

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 NPC274640 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	267
0.1-0.2	680
0.2-0.3	941
0.3-0.4	1395
0.4-0.5	2785
0.5-0.6	2202
0.6-0.7	731
0.7-0.8	148
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD6160	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7395	Discontinued
0.7824	Intermediate Similarity	NPD5429	Discontinued
0.7821	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6716	Phase 1
0.7807	Intermediate Similarity	NPD1867	Approved
0.7793	Intermediate Similarity	NPD5632	Approved
0.7773	Intermediate Similarity	NPD3746	Discontinued
0.7758	Intermediate Similarity	NPD3258	Approved
0.7748	Intermediate Similarity	NPD5164	Discontinued
0.7738	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7689	Intermediate Similarity	NPD5512	Phase 3
0.7658	Intermediate Similarity	NPD3257	Approved
0.7653	Intermediate Similarity	NPD5003	Discontinued
0.7634	Intermediate Similarity	NPD4429	Discontinued
0.7609	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD5416	Discontinued
0.7602	Intermediate Similarity	NPD4502	Phase 2
0.7597	Intermediate Similarity	NPD7853	Phase 2
0.7576	Intermediate Similarity	NPD1466	Phase 3
0.7576	Intermediate Similarity	NPD1467	Approved
0.7566	Intermediate Similarity	NPD6242	Discontinued
0.7544	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD5482	Discontinued
0.7536	Intermediate Similarity	NPD2564	Approved
0.7536	Intermediate Similarity	NPD2565	Phase 2
0.7532	Intermediate Similarity	NPD5479	Discontinued
0.7523	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD3259	Approved
0.7522	Intermediate Similarity	NPD4328	Approved
0.7511	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.751	Intermediate Similarity	NPD7708	Approved
0.75	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.749	Intermediate Similarity	NPD5488	Discontinued
0.7489	Intermediate Similarity	NPD5901	Discontinued
0.7467	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD5022	Discontinued
0.7447	Intermediate Similarity	NPD3006	Discontinued
0.7443	Intermediate Similarity	NPD2920	Discontinued
0.744	Intermediate Similarity	NPD8363	Approved
0.744	Intermediate Similarity	NPD8364	Approved
0.7425	Intermediate Similarity	NPD1505	Phase 2
0.7404	Intermediate Similarity	NPD2951	Discontinued
0.7397	Intermediate Similarity	NPD2779	Approved
0.7395	Intermediate Similarity	NPD7417	Discontinued
0.7395	Intermediate Similarity	NPD4418	Discontinued
0.739	Intermediate Similarity	NPD7803	Approved
0.7381	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7994	Phase 2
0.7342	Intermediate Similarity	NPD5805	Approved
0.7339	Intermediate Similarity	NPD2778	Approved
0.7339	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD7180	Phase 3
0.7328	Intermediate Similarity	NPD7955	Approved
0.7328	Intermediate Similarity	NPD7956	Approved
0.7321	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD4885	Approved
0.7301	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD3945	Discontinued
0.7288	Intermediate Similarity	NPD4373	Phase 2
0.7285	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD6456	Discontinued
0.7277	Intermediate Similarity	NPD6962	Phase 2
0.7277	Intermediate Similarity	NPD7688	Phase 1
0.7266	Intermediate Similarity	NPD8465	Approved
0.7266	Intermediate Similarity	NPD8427	Approved
0.7266	Intermediate Similarity	NPD8428	Approved
0.7266	Intermediate Similarity	NPD8467	Approved
0.7266	Intermediate Similarity	NPD8466	Approved
0.7266	Intermediate Similarity	NPD8429	Approved
0.726	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD3263	Phase 3
0.7243	Intermediate Similarity	NPD8358	Approved
0.7237	Intermediate Similarity	NPD5612	Discontinued
0.7234	Intermediate Similarity	NPD4952	Phase 3
0.722	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6974	Phase 3
0.7217	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6770	Approved
0.7212	Intermediate Similarity	NPD5939	Approved
0.7212	Intermediate Similarity	NPD5936	Approved
0.721	Intermediate Similarity	NPD3925	Approved
0.7198	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4368	Phase 2
0.7195	Intermediate Similarity	NPD4511	Phase 1
0.7193	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD1038	Approved
0.7186	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3986	Discontinued
0.7183	Intermediate Similarity	NPD5450	Discontinued
0.7182	Intermediate Similarity	NPD2175	Phase 3
0.7182	Intermediate Similarity	NPD2176	Approved
0.7182	Intermediate Similarity	NPD2177	Approved
0.7181	Intermediate Similarity	NPD7069	Discontinued
0.7181	Intermediate Similarity	NPD5866	Approved
0.7175	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3354	Phase 2
0.7166	Intermediate Similarity	NPD8463	Approved
0.716	Intermediate Similarity	NPD6530	Approved
0.716	Intermediate Similarity	NPD6531	Approved
0.7156	Intermediate Similarity	NPD5658	Approved
0.7155	Intermediate Similarity	NPD4454	Phase 2
0.7154	Intermediate Similarity	NPD8426	Approved
0.7154	Intermediate Similarity	NPD8425	Approved
0.7154	Intermediate Similarity	NPD8459	Approved
0.7154	Intermediate Similarity	NPD8460	Approved
0.7149	Intermediate Similarity	NPD3289	Phase 3
0.7149	Intermediate Similarity	NPD3290	Approved
0.7149	Intermediate Similarity	NPD6517	Phase 3
0.7149	Intermediate Similarity	NPD484	Approved
0.7143	Intermediate Similarity	NPD3003	Approved
0.7143	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6995	Phase 1
0.7123	Intermediate Similarity	NPD6550	Discontinued
0.7112	Intermediate Similarity	NPD5850	Phase 3
0.7111	Intermediate Similarity	NPD7222	Phase 2
0.7111	Intermediate Similarity	NPD7452	Approved
0.7111	Intermediate Similarity	NPD6290	Phase 2
0.7111	Intermediate Similarity	NPD7453	Approved
0.7107	Intermediate Similarity	NPD6790	Phase 1
0.7106	Intermediate Similarity	NPD7603	Discontinued
0.71	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6376	Discontinued
0.708	Intermediate Similarity	NPD8091	Phase 3
0.7078	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7925	Phase 2
0.7059	Intermediate Similarity	NPD7924	Phase 2
0.7048	Intermediate Similarity	NPD4506	Discontinued
0.7043	Intermediate Similarity	NPD5902	Approved
0.7043	Intermediate Similarity	NPD5903	Approved
0.7037	Intermediate Similarity	NPD4948	Discontinued
0.7036	Intermediate Similarity	NPD5399	Discovery
0.7032	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD3920	Phase 2
0.7022	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2844	Phase 3
0.7014	Intermediate Similarity	NPD6988	Phase 1
0.7004	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD8102	Discontinued
0.6987	Remote Similarity	NPD7470	Discontinued
0.6978	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7542	Phase 3
0.6947	Remote Similarity	NPD3947	Discontinued
0.6946	Remote Similarity	NPD6199	Discontinued
0.6942	Remote Similarity	NPD5891	Approved
0.6942	Remote Similarity	NPD3250	Phase 1
0.6941	Remote Similarity	NPD5913	Phase 3
0.6941	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD3243	Approved
0.6926	Remote Similarity	NPD8016	Phase 3
0.6926	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD4356	Discontinued
0.6923	Remote Similarity	NPD6590	Discontinued
0.6916	Remote Similarity	NPD5530	Phase 1
0.6914	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD7689	Approved
0.6905	Remote Similarity	NPD1325	Approved
0.6905	Remote Similarity	NPD1326	Approved
0.6895	Remote Similarity	NPD3328	Phase 2
0.6887	Remote Similarity	NPD4442	Phase 2
0.6885	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5924	Discontinued
0.6875	Remote Similarity	NPD1768	Approved
0.6875	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.687	Remote Similarity	NPD3392	Approved
0.6867	Remote Similarity	NPD7658	Phase 2
0.6867	Remote Similarity	NPD4558	Phase 2
0.6863	Remote Similarity	NPD8489	Phase 1
0.6861	Remote Similarity	NPD7948	Phase 1
0.6858	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD2916	Discontinued
0.6851	Remote Similarity	NPD3875	Discontinued
0.6849	Remote Similarity	NPD1534	Approved
0.6844	Remote Similarity	NPD4601	Approved
0.6844	Remote Similarity	NPD4600	Approved
0.6842	Remote Similarity	NPD6245	Phase 2
0.684	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.684	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.684	Remote Similarity	NPD4493	Discontinued
0.6835	Remote Similarity	NPD5256	Discontinued
0.6833	Remote Similarity	NPD5559	Phase 2
0.6828	Remote Similarity	NPD6176	Phase 1
0.6822	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.682	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7181	Phase 3
0.6818	Remote Similarity	NPD5151	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