NPASS Compound

Structure

NPC144452 OpenBabel07101718202D 24 26 0 0 0 0 0 0 0 0999 V2000 1.3566 4.9586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0446 5.9767 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 -0.2257 4.2541 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 -1.9890 1.8271 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 -0.4067 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 0.0000 -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 -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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 23 1 0 0 0 0 4 24 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 14 2 0 0 0 0 8 16 2 0 0 0 0 9 10 1 0 0 0 0 9 12 2 0 0 0 0 10 13 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 13 15 1 0 0 0 0 13 18 2 0 0 0 0 14 16 1 0 0 0 0 14 18 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 19 21 1 0 0 0 0 20 22 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	323.15
Volume:	345.083
LogP:	5.547
LogD:	4.132
LogS:	-6.06
# Rotatable Bonds:	5
TPSA:	51.32
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.563
Synthetic Accessibility Score:	2.51
Fsp3:	0.25
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:	-4.925
MDCK Permeability:	1.4335098057927098e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.057
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.304
Plasma Protein Binding (PPB):	86.1957778930664%
Volume Distribution (VD):	0.837
Pgp-substrate:	6.052857875823975%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.925
CYP2C19-inhibitor:	0.966
CYP2C19-substrate:	0.273
CYP2C9-inhibitor:	0.916
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.666
CYP2D6-substrate:	0.815
CYP3A4-inhibitor:	0.687
CYP3A4-substrate:	0.201

ADMET: Excretion

Clearance (CL):	8.61
Half-life (T1/2):	0.208

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.854
Drug-inuced Liver Injury (DILI):	0.815
AMES Toxicity:	0.066
Rat Oral Acute Toxicity:	0.118
Maximum Recommended Daily Dose:	0.47
Skin Sensitization:	0.89
Carcinogencity:	0.184
Eye Corrosion:	0.005
Eye Irritation:	0.451
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC144452

Natural Product ID:	NPC144452
*Common Name:**	Clausamine
IUPAC Name:	methyl 1-methoxy-4-(3-methylbut-2-enyl)-9H-carbazole-3-carboxylate
Synonyms:	Clausamine; Clausamine D
Standard InCHIKey:	YTUBOXOSIHCYQX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H21NO3/c1-12(2)9-10-13-15(20(22)24-4)11-17(23-3)19-18(13)14-7-5-6-8-16(14)21-19/h5-9,11,21H,10H2,1-4H3
SMILES:	COC(=O)c1cc(OC)c2c(c1CC=C(C)C)c1ccccc1[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480857
PubChem CID:	10041876
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	8

Activity Type	# Activity
Cell Line	4
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[504564]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[504564]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[504564]
NPT2	Others	Unspecified		Activity	=	18.2	%	PMID[504564]
NPT2	Others	Unspecified		Activity	=	34.2	%	PMID[504564]
NPT2	Others	Unspecified		Activity	=	66.0	%	PMID[504564]
NPT2	Others	Unspecified		Activity	=	92.3	%	PMID[504564]

☑ 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 NPC144452 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	461
0.1-0.2	2951
0.2-0.3	12445
0.3-0.4	4663
0.4-0.5	16192
0.5-0.6	3814
0.6-0.7	1668
0.7-0.8	447
0.8-0.85	33
0.85-0.9	11
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9752	High Similarity	NPC274640
0.9657	High Similarity	NPC474688
0.96	High Similarity	NPC225279
0.9594	High Similarity	NPC39500
0.9458	High Similarity	NPC51388
0.9403	High Similarity	NPC184408
0.9292	High Similarity	NPC475844
0.92	High Similarity	NPC187501
0.9167	High Similarity	NPC208084
0.9095	High Similarity	NPC474701
0.9064	High Similarity	NPC118228
0.895	High Similarity	NPC300156
0.8905	High Similarity	NPC4687
0.8894	High Similarity	NPC280799
0.8883	High Similarity	NPC293151
0.8857	High Similarity	NPC179287
0.8732	High Similarity	NPC87413
0.867	High Similarity	NPC45190
0.8627	High Similarity	NPC249583
0.8618	High Similarity	NPC39370
0.8612	High Similarity	NPC169402
0.8606	High Similarity	NPC116238
0.8525	High Similarity	NPC473186
0.8502	High Similarity	NPC199667
0.8495	Intermediate Similarity	NPC39679
0.8477	Intermediate Similarity	NPC242928
0.8454	Intermediate Similarity	NPC473181
0.8447	Intermediate Similarity	NPC283117
0.8421	Intermediate Similarity	NPC308137
0.8421	Intermediate Similarity	NPC310211
0.8404	Intermediate Similarity	NPC174760
0.8396	Intermediate Similarity	NPC46561
0.838	Intermediate Similarity	NPC470018
0.8376	Intermediate Similarity	NPC160381
0.8374	Intermediate Similarity	NPC128823
0.8373	Intermediate Similarity	NPC294375
0.8357	Intermediate Similarity	NPC321428
0.8318	Intermediate Similarity	NPC150239
0.8308	Intermediate Similarity	NPC475190
0.8286	Intermediate Similarity	NPC9894
0.8279	Intermediate Similarity	NPC198503
0.8273	Intermediate Similarity	NPC49547
0.8246	Intermediate Similarity	NPC473180
0.8224	Intermediate Similarity	NPC247803
0.8216	Intermediate Similarity	NPC3207
0.8206	Intermediate Similarity	NPC6786
0.8174	Intermediate Similarity	NPC74575
0.8173	Intermediate Similarity	NPC474798
0.8086	Intermediate Similarity	NPC470930
0.8009	Intermediate Similarity	NPC193777
0.7991	Intermediate Similarity	NPC208522
0.7991	Intermediate Similarity	NPC94157
0.7944	Intermediate Similarity	NPC23294
0.7936	Intermediate Similarity	NPC473179
0.792	Intermediate Similarity	NPC470017
0.7913	Intermediate Similarity	NPC131017
0.7897	Intermediate Similarity	NPC303951
0.789	Intermediate Similarity	NPC473041
0.789	Intermediate Similarity	NPC96321
0.7854	Intermediate Similarity	NPC288987
0.785	Intermediate Similarity	NPC201697
0.7837	Intermediate Similarity	NPC243834
0.7837	Intermediate Similarity	NPC70956
0.7832	Intermediate Similarity	NPC473182
0.7818	Intermediate Similarity	NPC132642
0.7814	Intermediate Similarity	NPC470020
0.7804	Intermediate Similarity	NPC86834
0.7804	Intermediate Similarity	NPC210828
0.7799	Intermediate Similarity	NPC72211
0.7783	Intermediate Similarity	NPC162484
0.7767	Intermediate Similarity	NPC209769
0.7746	Intermediate Similarity	NPC132539
0.7745	Intermediate Similarity	NPC473188
0.7743	Intermediate Similarity	NPC260434
0.7742	Intermediate Similarity	NPC48353
0.7741	Intermediate Similarity	NPC89549
0.7731	Intermediate Similarity	NPC471304
0.7729	Intermediate Similarity	NPC470022
0.7723	Intermediate Similarity	NPC202503
0.7703	Intermediate Similarity	NPC70259
0.7692	Intermediate Similarity	NPC230403
0.7689	Intermediate Similarity	NPC478078
0.7689	Intermediate Similarity	NPC473185
0.7689	Intermediate Similarity	NPC257851
0.7686	Intermediate Similarity	NPC473187
0.7675	Intermediate Similarity	NPC329631
0.7661	Intermediate Similarity	NPC474428
0.7661	Intermediate Similarity	NPC38237
0.766	Intermediate Similarity	NPC270515
0.7656	Intermediate Similarity	NPC43787
0.7656	Intermediate Similarity	NPC205934
0.7655	Intermediate Similarity	NPC194740
0.7652	Intermediate Similarity	NPC15801
0.7636	Intermediate Similarity	NPC152768
0.7636	Intermediate Similarity	NPC148183
0.7629	Intermediate Similarity	NPC148889
0.7615	Intermediate Similarity	NPC146418
0.7615	Intermediate Similarity	NPC208284
0.7606	Intermediate Similarity	NPC267423
0.76	Intermediate Similarity	NPC21638
0.7593	Intermediate Similarity	NPC191489
0.7588	Intermediate Similarity	NPC475253
0.7585	Intermediate Similarity	NPC246700
0.7583	Intermediate Similarity	NPC153042
0.7578	Intermediate Similarity	NPC472099
0.7578	Intermediate Similarity	NPC323969
0.7577	Intermediate Similarity	NPC311906
0.757	Intermediate Similarity	NPC291535
0.757	Intermediate Similarity	NPC475112
0.757	Intermediate Similarity	NPC475085
0.7568	Intermediate Similarity	NPC131885
0.7568	Intermediate Similarity	NPC303658
0.7546	Intermediate Similarity	NPC476106
0.7545	Intermediate Similarity	NPC324361
0.7545	Intermediate Similarity	NPC476287
0.7542	Intermediate Similarity	NPC478083
0.7533	Intermediate Similarity	NPC157931
0.7525	Intermediate Similarity	NPC84347
0.7523	Intermediate Similarity	NPC314552
0.7523	Intermediate Similarity	NPC312645
0.7521	Intermediate Similarity	NPC67401
0.7512	Intermediate Similarity	NPC176127
0.75	Intermediate Similarity	NPC132385
0.75	Intermediate Similarity	NPC471762
0.7489	Intermediate Similarity	NPC253675
0.7489	Intermediate Similarity	NPC142385
0.7479	Intermediate Similarity	NPC165964
0.7478	Intermediate Similarity	NPC474192
0.7478	Intermediate Similarity	NPC475720
0.7477	Intermediate Similarity	NPC36405
0.7476	Intermediate Similarity	NPC84478
0.7469	Intermediate Similarity	NPC88923
0.7469	Intermediate Similarity	NPC315634
0.7469	Intermediate Similarity	NPC53534
0.7469	Intermediate Similarity	NPC100734
0.7467	Intermediate Similarity	NPC60621
0.7466	Intermediate Similarity	NPC89508
0.7465	Intermediate Similarity	NPC306376
0.7454	Intermediate Similarity	NPC223427
0.7454	Intermediate Similarity	NPC476138
0.7454	Intermediate Similarity	NPC245816
0.7444	Intermediate Similarity	NPC305984
0.7443	Intermediate Similarity	NPC325297
0.7442	Intermediate Similarity	NPC476044
0.7425	Intermediate Similarity	NPC473183
0.7424	Intermediate Similarity	NPC252251
0.7421	Intermediate Similarity	NPC118940
0.7418	Intermediate Similarity	NPC141454
0.7416	Intermediate Similarity	NPC128751
0.7414	Intermediate Similarity	NPC473184
0.7407	Intermediate Similarity	NPC284685
0.7406	Intermediate Similarity	NPC276517
0.7404	Intermediate Similarity	NPC477066
0.7403	Intermediate Similarity	NPC132329
0.7401	Intermediate Similarity	NPC122436
0.7399	Intermediate Similarity	NPC330009
0.7399	Intermediate Similarity	NPC469928
0.7395	Intermediate Similarity	NPC329747
0.7387	Intermediate Similarity	NPC118511
0.7381	Intermediate Similarity	NPC469497
0.7381	Intermediate Similarity	NPC106833
0.7377	Intermediate Similarity	NPC185197
0.7373	Intermediate Similarity	NPC473540
0.7373	Intermediate Similarity	NPC478081
0.7373	Intermediate Similarity	NPC476098
0.7373	Intermediate Similarity	NPC165599
0.7373	Intermediate Similarity	NPC478082
0.7373	Intermediate Similarity	NPC477067
0.7371	Intermediate Similarity	NPC473105
0.7366	Intermediate Similarity	NPC88363
0.7362	Intermediate Similarity	NPC41501
0.7362	Intermediate Similarity	NPC475816
0.7359	Intermediate Similarity	NPC477531
0.7358	Intermediate Similarity	NPC152620
0.7356	Intermediate Similarity	NPC94943
0.7354	Intermediate Similarity	NPC477979
0.7353	Intermediate Similarity	NPC475666
0.735	Intermediate Similarity	NPC472061
0.7349	Intermediate Similarity	NPC280714
0.7348	Intermediate Similarity	NPC66777
0.7342	Intermediate Similarity	NPC472098
0.7333	Intermediate Similarity	NPC174576
0.7327	Intermediate Similarity	NPC135887
0.7327	Intermediate Similarity	NPC199277
0.7325	Intermediate Similarity	NPC205372
0.7325	Intermediate Similarity	NPC472589
0.7322	Intermediate Similarity	NPC17437
0.7321	Intermediate Similarity	NPC194040
0.7319	Intermediate Similarity	NPC101350
0.7317	Intermediate Similarity	NPC230683
0.7316	Intermediate Similarity	NPC209174
0.7315	Intermediate Similarity	NPC329793
0.7314	Intermediate Similarity	NPC472588
0.7311	Intermediate Similarity	NPC81939
0.7308	Intermediate Similarity	NPC190007
0.7304	Intermediate Similarity	NPC140296
0.7303	Intermediate Similarity	NPC137353
0.7303	Intermediate Similarity	NPC473800
0.7301	Intermediate Similarity	NPC74360
0.73	Intermediate Similarity	NPC72905

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 NPC144452 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	689
0.2-0.3	1010
0.3-0.4	1340
0.4-0.5	2891
0.5-0.6	2084
0.6-0.7	720
0.7-0.8	115
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9126	High Similarity	NPD6160	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD5632	Approved
0.7913	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD5429	Discontinued
0.7822	Intermediate Similarity	NPD1867	Approved
0.7808	Intermediate Similarity	NPD7395	Discontinued
0.7808	Intermediate Similarity	NPD4429	Discontinued
0.7752	Intermediate Similarity	NPD3257	Approved
0.7738	Intermediate Similarity	NPD6242	Discontinued
0.7703	Intermediate Similarity	NPD5512	Phase 3
0.7699	Intermediate Similarity	NPD5479	Discontinued
0.7692	Intermediate Similarity	NPD3258	Approved
0.7675	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD6716	Phase 1
0.7671	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD3746	Discontinued
0.7627	Intermediate Similarity	NPD5482	Discontinued
0.7609	Intermediate Similarity	NPD3006	Discontinued
0.7593	Intermediate Similarity	NPD7708	Approved
0.7589	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD5003	Discontinued
0.7544	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD5416	Discontinued
0.7532	Intermediate Similarity	NPD7853	Phase 2
0.7523	Intermediate Similarity	NPD5164	Discontinued
0.7512	Intermediate Similarity	NPD2778	Approved
0.7511	Intermediate Similarity	NPD1466	Phase 3
0.7511	Intermediate Similarity	NPD1467	Approved
0.7489	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD4418	Discontinued
0.7478	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7803	Approved
0.7467	Intermediate Similarity	NPD5022	Discontinued
0.7466	Intermediate Similarity	NPD3945	Discontinued
0.7464	Intermediate Similarity	NPD2565	Phase 2
0.7464	Intermediate Similarity	NPD2564	Approved
0.7456	Intermediate Similarity	NPD7994	Phase 2
0.7456	Intermediate Similarity	NPD4328	Approved
0.7456	Intermediate Similarity	NPD3259	Approved
0.7455	Intermediate Similarity	NPD4502	Phase 2
0.743	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5901	Discontinued
0.7407	Intermediate Similarity	NPD7955	Approved
0.7407	Intermediate Similarity	NPD2779	Approved
0.7407	Intermediate Similarity	NPD7956	Approved
0.7403	Intermediate Similarity	NPD4885	Approved
0.7399	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD2920	Discontinued
0.7359	Intermediate Similarity	NPD1505	Phase 2
0.7359	Intermediate Similarity	NPD7688	Phase 1
0.7353	Intermediate Similarity	NPD5488	Discontinued
0.7339	Intermediate Similarity	NPD2951	Discontinued
0.7322	Intermediate Similarity	NPD8358	Approved
0.7318	Intermediate Similarity	NPD5658	Approved
0.7316	Intermediate Similarity	NPD4952	Phase 3
0.7315	Intermediate Similarity	NPD3289	Phase 3
0.7315	Intermediate Similarity	NPD3290	Approved
0.7309	Intermediate Similarity	NPD8364	Approved
0.7309	Intermediate Similarity	NPD8363	Approved
0.7304	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6770	Approved
0.7269	Intermediate Similarity	NPD7180	Phase 3
0.7258	Intermediate Similarity	NPD5450	Discontinued
0.7257	Intermediate Similarity	NPD7417	Discontinued
0.7251	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4373	Phase 2
0.7217	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.721	Intermediate Similarity	NPD6962	Phase 2
0.7209	Intermediate Similarity	NPD6550	Discontinued
0.7203	Intermediate Similarity	NPD5805	Approved
0.7198	Intermediate Similarity	NPD3920	Phase 2
0.7198	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD1038	Approved
0.7185	Intermediate Similarity	NPD6790	Phase 1
0.7182	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD6456	Discontinued
0.7149	Intermediate Similarity	NPD3003	Approved
0.7149	Intermediate Similarity	NPD6974	Phase 3
0.7143	Intermediate Similarity	NPD5936	Approved
0.7143	Intermediate Similarity	NPD5939	Approved
0.7143	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD8428	Approved
0.7137	Intermediate Similarity	NPD8467	Approved
0.7137	Intermediate Similarity	NPD8427	Approved
0.7137	Intermediate Similarity	NPD8466	Approved
0.7137	Intermediate Similarity	NPD8465	Approved
0.7137	Intermediate Similarity	NPD8429	Approved
0.7136	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD4368	Phase 2
0.713	Intermediate Similarity	NPD4506	Discontinued
0.713	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6995	Phase 1
0.7124	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4511	Phase 1
0.7118	Intermediate Similarity	NPD5850	Phase 3
0.7112	Intermediate Similarity	NPD3263	Phase 3
0.7111	Intermediate Similarity	NPD7069	Discontinued
0.7111	Intermediate Similarity	NPD5866	Approved
0.711	Intermediate Similarity	NPD2177	Approved
0.711	Intermediate Similarity	NPD2176	Approved
0.711	Intermediate Similarity	NPD2175	Phase 3
0.7105	Intermediate Similarity	NPD3354	Phase 2
0.7104	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6530	Approved
0.7097	Intermediate Similarity	NPD6531	Approved
0.7093	Intermediate Similarity	NPD5612	Discontinued
0.7089	Intermediate Similarity	NPD3250	Phase 1
0.7083	Intermediate Similarity	NPD6517	Phase 3
0.708	Intermediate Similarity	NPD4356	Discontinued
0.7078	Intermediate Similarity	NPD484	Approved
0.7076	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD3925	Approved
0.7049	Intermediate Similarity	NPD3986	Discontinued
0.7043	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD7453	Approved
0.704	Intermediate Similarity	NPD7452	Approved
0.704	Intermediate Similarity	NPD7222	Phase 2
0.7033	Intermediate Similarity	NPD8463	Approved
0.7027	Intermediate Similarity	NPD8459	Approved
0.7027	Intermediate Similarity	NPD3947	Discontinued
0.7027	Intermediate Similarity	NPD8460	Approved
0.7027	Intermediate Similarity	NPD8425	Approved
0.7027	Intermediate Similarity	NPD8426	Approved
0.7023	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD5913	Phase 3
0.7021	Intermediate Similarity	NPD5924	Discontinued
0.7018	Intermediate Similarity	NPD6988	Phase 1
0.7017	Intermediate Similarity	NPD5891	Approved
0.7017	Intermediate Similarity	NPD4454	Phase 2
0.7009	Intermediate Similarity	NPD6376	Discontinued
0.7008	Intermediate Similarity	NPD4558	Phase 2
0.7005	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD7924	Phase 2
0.6996	Remote Similarity	NPD7925	Phase 2
0.6996	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD6245	Phase 2
0.6995	Remote Similarity	NPD5256	Discontinued
0.6991	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6176	Phase 1
0.6981	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5559	Phase 2
0.6974	Remote Similarity	NPD5902	Approved
0.6974	Remote Similarity	NPD5903	Approved
0.6972	Remote Similarity	NPD5399	Discovery
0.6966	Remote Similarity	NPD7603	Discontinued
0.6964	Remote Similarity	NPD6290	Phase 2
0.6963	Remote Similarity	NPD4948	Discontinued
0.6955	Remote Similarity	NPD3825	Phase 3
0.6951	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD8091	Phase 3
0.6942	Remote Similarity	NPD2844	Phase 3
0.6942	Remote Similarity	NPD2680	Approved
0.6942	Remote Similarity	NPD2681	Approved
0.6939	Remote Similarity	NPD8102	Discontinued
0.6933	Remote Similarity	NPD2509	Approved
0.6933	Remote Similarity	NPD2510	Approved
0.6926	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4501	Approved
0.6923	Remote Similarity	NPD4500	Approved
0.692	Remote Similarity	NPD7010	Phase 3
0.6916	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5475	Discontinued
0.6916	Remote Similarity	NPD7470	Discontinued
0.6909	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4442	Phase 2
0.6884	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD1768	Approved
0.6872	Remote Similarity	NPD3392	Approved
0.6858	Remote Similarity	NPD7467	Discontinued
0.6852	Remote Similarity	NPD1534	Approved
0.6849	Remote Similarity	NPD6590	Discontinued
0.6847	Remote Similarity	NPD4601	Approved
0.6847	Remote Similarity	NPD4600	Approved
0.6844	Remote Similarity	NPD8403	Phase 1
0.6844	Remote Similarity	NPD5530	Phase 1
0.6842	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3922	Approved
0.6835	Remote Similarity	NPD3923	Approved
0.6835	Remote Similarity	NPD3924	Approved
0.6835	Remote Similarity	NPD3921	Approved
0.6828	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD1325	Approved
0.6827	Remote Similarity	NPD1326	Approved
0.6826	Remote Similarity	NPD5293	Phase 2
0.682	Remote Similarity	NPD4499	Approved
0.6818	Remote Similarity	NPD4394	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