NPASS Compound

Structure

NPC475844 OpenBabel07101718322D 24 27 0 0 1 0 0 0 0 0999 V2000 -0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1340 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9504 0.1729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5382 0.9819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9559 0.2774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1314 1.8955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 2.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 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 19 1 0 0 0 0 2 19 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 10 2 0 0 0 0 7 13 2 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 10 16 1 0 0 0 0 11 12 1 0 0 0 0 11 16 2 0 0 0 0 12 18 1 0 0 0 0 13 20 1 0 0 0 0 14 17 2 0 0 0 0 14 23 1 0 0 0 0 15 19 1 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 18 24 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	325.13
Volume:	330.657
LogP:	3.757
LogD:	3.038
LogS:	-3.966
# Rotatable Bonds:	2
TPSA:	71.55
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.71
Synthetic Accessibility Score:	3.155
Fsp3:	0.316
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:	-4.946
MDCK Permeability:	1.3999097973282915e-05
Pgp-inhibitor:	0.444
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.522
Plasma Protein Binding (PPB):	88.6046371459961%
Volume Distribution (VD):	0.788
Pgp-substrate:	6.423210144042969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.911
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.466
CYP2C19-substrate:	0.456
CYP2C9-inhibitor:	0.505
CYP2C9-substrate:	0.932
CYP2D6-inhibitor:	0.678
CYP2D6-substrate:	0.546
CYP3A4-inhibitor:	0.459
CYP3A4-substrate:	0.246

ADMET: Excretion

Clearance (CL):	6.468
Half-life (T1/2):	0.643

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.127
Drug-inuced Liver Injury (DILI):	0.741
AMES Toxicity:	0.205
Rat Oral Acute Toxicity:	0.109
Maximum Recommended Daily Dose:	0.798
Skin Sensitization:	0.592
Carcinogencity:	0.603
Eye Corrosion:	0.005
Eye Irritation:	0.276
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC475844

Natural Product ID:	NPC475844
*Common Name:**	Clausamine C
IUPAC Name:	2-(2-hydroxypropan-2-yl)-6-methoxy-2,7-dihydro-1H-pyrano[3,4-c]carbazol-4-one
Synonyms:	Clausamine C
Standard InCHIKey:	UWUXJRWRYLZZIF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H19NO4/c1-19(2,22)15-9-11-12(18(21)24-15)8-14(23-3)17-16(11)10-6-4-5-7-13(10)20-17/h4-8,15,20,22H,9H2,1-3H3
SMILES:	CC(C)(C1CC2=C3C4=CC=CC=C4NC3=C(C=C2C(=O)O1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517226
PubChem CID:	10448976
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.	leaf	n.a.	DOI[10.1080/10412905.1999.9701119]
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.	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	9

Activity Type	# Activity
Cell Line	5
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[460907]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[460907]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[460907]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	79.7	%	PMID[460908]
NPT2	Others	Unspecified		Activity	=	12.4	%	PMID[460907]
NPT2	Others	Unspecified		Activity	=	27.2	%	PMID[460907]
NPT2	Others	Unspecified		Activity	=	72.0	%	PMID[460907]
NPT2	Others	Unspecified		Activity	=	92.3	%	PMID[460907]

☑ 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 NPC475844 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	403
0.1-0.2	2104
0.2-0.3	8766
0.3-0.4	8773
0.4-0.5	11659
0.5-0.6	8644
0.6-0.7	1865
0.7-0.8	441
0.8-0.85	26
0.85-0.9	8
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9623	High Similarity	NPC474688
0.9437	High Similarity	NPC274640
0.9349	High Similarity	NPC474701
0.9292	High Similarity	NPC144452
0.907	High Similarity	NPC51388
0.9019	High Similarity	NPC225279
0.9014	High Similarity	NPC184408
0.8915	High Similarity	NPC39500
0.8698	High Similarity	NPC118228
0.8645	High Similarity	NPC187501
0.8624	High Similarity	NPC208084
0.8618	High Similarity	NPC293151
0.8597	High Similarity	NPC179287
0.8545	High Similarity	NPC280799
0.8387	Intermediate Similarity	NPC87413
0.8326	Intermediate Similarity	NPC300156
0.8287	Intermediate Similarity	NPC4687
0.8225	Intermediate Similarity	NPC6786
0.8217	Intermediate Similarity	NPC39370
0.8203	Intermediate Similarity	NPC283117
0.817	Intermediate Similarity	NPC174760
0.8165	Intermediate Similarity	NPC39679
0.8157	Intermediate Similarity	NPC45190
0.8136	Intermediate Similarity	NPC294375
0.8131	Intermediate Similarity	NPC128823
0.813	Intermediate Similarity	NPC473186
0.8119	Intermediate Similarity	NPC249583
0.8117	Intermediate Similarity	NPC169402
0.8089	Intermediate Similarity	NPC150239
0.8054	Intermediate Similarity	NPC9894
0.8053	Intermediate Similarity	NPC198503
0.8037	Intermediate Similarity	NPC321428
0.8027	Intermediate Similarity	NPC116238
0.8009	Intermediate Similarity	NPC199667
0.8	Intermediate Similarity	NPC247803
0.7991	Intermediate Similarity	NPC470018
0.7964	Intermediate Similarity	NPC473181
0.7941	Intermediate Similarity	NPC208522
0.7937	Intermediate Similarity	NPC310211
0.7937	Intermediate Similarity	NPC308137
0.792	Intermediate Similarity	NPC46561
0.7918	Intermediate Similarity	NPC89549
0.7911	Intermediate Similarity	NPC3207
0.7897	Intermediate Similarity	NPC49547
0.7877	Intermediate Similarity	NPC242928
0.7863	Intermediate Similarity	NPC473182
0.7851	Intermediate Similarity	NPC473188
0.7846	Intermediate Similarity	NPC191489
0.7814	Intermediate Similarity	NPC475190
0.781	Intermediate Similarity	NPC165964
0.7802	Intermediate Similarity	NPC74575
0.7797	Intermediate Similarity	NPC312645
0.7783	Intermediate Similarity	NPC470930
0.7783	Intermediate Similarity	NPC160381
0.7778	Intermediate Similarity	NPC473800
0.7778	Intermediate Similarity	NPC473180
0.7751	Intermediate Similarity	NPC132385
0.7745	Intermediate Similarity	NPC474192
0.7745	Intermediate Similarity	NPC475720
0.7733	Intermediate Similarity	NPC23294
0.7729	Intermediate Similarity	NPC473179
0.7723	Intermediate Similarity	NPC209769
0.772	Intermediate Similarity	NPC100734
0.772	Intermediate Similarity	NPC88923
0.772	Intermediate Similarity	NPC315634
0.7713	Intermediate Similarity	NPC193777
0.7705	Intermediate Similarity	NPC67401
0.7699	Intermediate Similarity	NPC48353
0.7696	Intermediate Similarity	NPC132642
0.7695	Intermediate Similarity	NPC270515
0.7689	Intermediate Similarity	NPC303951
0.7668	Intermediate Similarity	NPC476106
0.7665	Intermediate Similarity	NPC89508
0.7652	Intermediate Similarity	NPC472589
0.7652	Intermediate Similarity	NPC288987
0.7647	Intermediate Similarity	NPC473187
0.7647	Intermediate Similarity	NPC470017
0.7642	Intermediate Similarity	NPC472588
0.7642	Intermediate Similarity	NPC314552
0.7639	Intermediate Similarity	NPC21638
0.7637	Intermediate Similarity	NPC329631
0.7637	Intermediate Similarity	NPC473105
0.7625	Intermediate Similarity	NPC475816
0.7607	Intermediate Similarity	NPC202503
0.76	Intermediate Similarity	NPC86834
0.76	Intermediate Similarity	NPC210828
0.7594	Intermediate Similarity	NPC474798
0.7588	Intermediate Similarity	NPC195788
0.7588	Intermediate Similarity	NPC237901
0.7573	Intermediate Similarity	NPC57453
0.7566	Intermediate Similarity	NPC201697
0.7545	Intermediate Similarity	NPC243834
0.7545	Intermediate Similarity	NPC70956
0.7544	Intermediate Similarity	NPC94157
0.7541	Intermediate Similarity	NPC58209
0.7534	Intermediate Similarity	NPC291535
0.7534	Intermediate Similarity	NPC475085
0.7534	Intermediate Similarity	NPC475112
0.7532	Intermediate Similarity	NPC96321
0.7532	Intermediate Similarity	NPC473041
0.7521	Intermediate Similarity	NPC94842
0.752	Intermediate Similarity	NPC284685
0.7511	Intermediate Similarity	NPC232225
0.7511	Intermediate Similarity	NPC72211
0.751	Intermediate Similarity	NPC470785
0.75	Intermediate Similarity	NPC162484
0.75	Intermediate Similarity	NPC478078
0.75	Intermediate Similarity	NPC473185
0.7489	Intermediate Similarity	NPC230403
0.7479	Intermediate Similarity	NPC41501
0.7471	Intermediate Similarity	NPC260909
0.7469	Intermediate Similarity	NPC470022
0.7469	Intermediate Similarity	NPC15801
0.7469	Intermediate Similarity	NPC184680
0.7469	Intermediate Similarity	NPC473183
0.7468	Intermediate Similarity	NPC194740
0.7468	Intermediate Similarity	NPC472099
0.7468	Intermediate Similarity	NPC252251
0.7458	Intermediate Similarity	NPC473184
0.7458	Intermediate Similarity	NPC253675
0.7456	Intermediate Similarity	NPC470020
0.7449	Intermediate Similarity	NPC148889
0.7446	Intermediate Similarity	NPC152768
0.7446	Intermediate Similarity	NPC148183
0.7423	Intermediate Similarity	NPC172355
0.7421	Intermediate Similarity	NPC70259
0.7418	Intermediate Similarity	NPC124300
0.7412	Intermediate Similarity	NPC227824
0.7412	Intermediate Similarity	NPC325297
0.7411	Intermediate Similarity	NPC267423
0.7406	Intermediate Similarity	NPC477531
0.7401	Intermediate Similarity	NPC244741
0.7399	Intermediate Similarity	NPC280714
0.7395	Intermediate Similarity	NPC311906
0.7388	Intermediate Similarity	NPC291609
0.7384	Intermediate Similarity	NPC200888
0.7381	Intermediate Similarity	NPC129897
0.738	Intermediate Similarity	NPC471304
0.7377	Intermediate Similarity	NPC49672
0.7376	Intermediate Similarity	NPC205934
0.7376	Intermediate Similarity	NPC43787
0.7376	Intermediate Similarity	NPC131017
0.7366	Intermediate Similarity	NPC470784
0.7364	Intermediate Similarity	NPC209174
0.7353	Intermediate Similarity	NPC257851
0.7349	Intermediate Similarity	NPC181081
0.7348	Intermediate Similarity	NPC220337
0.7347	Intermediate Similarity	NPC166712
0.7345	Intermediate Similarity	NPC165599
0.7345	Intermediate Similarity	NPC223427
0.7344	Intermediate Similarity	NPC22481
0.7341	Intermediate Similarity	NPC258048
0.7333	Intermediate Similarity	NPC260434
0.7333	Intermediate Similarity	NPC475253
0.7328	Intermediate Similarity	NPC146976
0.7328	Intermediate Similarity	NPC310618
0.7317	Intermediate Similarity	NPC142385
0.7317	Intermediate Similarity	NPC160100
0.7317	Intermediate Similarity	NPC188400
0.7316	Intermediate Similarity	NPC38237
0.7313	Intermediate Similarity	NPC132539
0.7309	Intermediate Similarity	NPC153042
0.7308	Intermediate Similarity	NPC303658
0.7308	Intermediate Similarity	NPC471303
0.7308	Intermediate Similarity	NPC131885
0.7306	Intermediate Similarity	NPC246700
0.7303	Intermediate Similarity	NPC132329
0.7302	Intermediate Similarity	NPC478083
0.7301	Intermediate Similarity	NPC199277
0.7301	Intermediate Similarity	NPC135887
0.73	Intermediate Similarity	NPC205372
0.7296	Intermediate Similarity	NPC74969
0.7296	Intermediate Similarity	NPC469928
0.7296	Intermediate Similarity	NPC330009
0.7294	Intermediate Similarity	NPC194040
0.7292	Intermediate Similarity	NPC24019
0.7288	Intermediate Similarity	NPC60621
0.7287	Intermediate Similarity	NPC160898
0.7284	Intermediate Similarity	NPC236668
0.7283	Intermediate Similarity	NPC185197
0.728	Intermediate Similarity	NPC133609
0.7273	Intermediate Similarity	NPC208284
0.7266	Intermediate Similarity	NPC152620
0.7259	Intermediate Similarity	NPC101312
0.7257	Intermediate Similarity	NPC476044
0.7257	Intermediate Similarity	NPC210434
0.7254	Intermediate Similarity	NPC182907
0.7254	Intermediate Similarity	NPC189903
0.7253	Intermediate Similarity	NPC477979
0.7246	Intermediate Similarity	NPC323969
0.7244	Intermediate Similarity	NPC32200
0.7243	Intermediate Similarity	NPC34770
0.7241	Intermediate Similarity	NPC475778
0.7236	Intermediate Similarity	NPC210296
0.7234	Intermediate Similarity	NPC469594
0.7234	Intermediate Similarity	NPC174576
0.7233	Intermediate Similarity	NPC318068
0.7232	Intermediate Similarity	NPC141454
0.7229	Intermediate Similarity	NPC219664
0.7229	Intermediate Similarity	NPC234999

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 NPC475844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	651
0.2-0.3	895
0.3-0.4	1652
0.4-0.5	2664
0.5-0.6	2196
0.6-0.7	691
0.7-0.8	129
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8848	High Similarity	NPD6160	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD6716	Phase 1
0.792	Intermediate Similarity	NPD7395	Discontinued
0.7873	Intermediate Similarity	NPD5429	Discontinued
0.7846	Intermediate Similarity	NPD7708	Approved
0.7841	Intermediate Similarity	NPD5632	Approved
0.7792	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5512	Phase 3
0.772	Intermediate Similarity	NPD7803	Approved
0.7709	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD5003	Discontinued
0.7702	Intermediate Similarity	NPD6962	Phase 2
0.766	Intermediate Similarity	NPD5022	Discontinued
0.7642	Intermediate Similarity	NPD5164	Discontinued
0.7637	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD8363	Approved
0.7628	Intermediate Similarity	NPD8364	Approved
0.7627	Intermediate Similarity	NPD1867	Approved
0.7588	Intermediate Similarity	NPD8467	Approved
0.7588	Intermediate Similarity	NPD8465	Approved
0.7588	Intermediate Similarity	NPD8466	Approved
0.7577	Intermediate Similarity	NPD4502	Phase 2
0.7577	Intermediate Similarity	NPD5416	Discontinued
0.7574	Intermediate Similarity	NPD4328	Approved
0.7573	Intermediate Similarity	NPD7853	Phase 2
0.7573	Intermediate Similarity	NPD3006	Discontinued
0.7569	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD6456	Discontinued
0.7521	Intermediate Similarity	NPD3746	Discontinued
0.7521	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD7956	Approved
0.752	Intermediate Similarity	NPD5482	Discontinued
0.752	Intermediate Similarity	NPD7955	Approved
0.7519	Intermediate Similarity	NPD8428	Approved
0.7519	Intermediate Similarity	NPD8429	Approved
0.7519	Intermediate Similarity	NPD8427	Approved
0.7512	Intermediate Similarity	NPD2564	Approved
0.7512	Intermediate Similarity	NPD2565	Phase 2
0.7511	Intermediate Similarity	NPD5479	Discontinued
0.75	Intermediate Similarity	NPD3258	Approved
0.75	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.749	Intermediate Similarity	NPD4373	Phase 2
0.7479	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD8426	Approved
0.7471	Intermediate Similarity	NPD8425	Approved
0.7471	Intermediate Similarity	NPD8460	Approved
0.7471	Intermediate Similarity	NPD8459	Approved
0.7457	Intermediate Similarity	NPD4429	Discontinued
0.7437	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD2920	Discontinued
0.7418	Intermediate Similarity	NPD6517	Phase 3
0.7371	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD4952	Phase 3
0.7359	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD6531	Approved
0.7352	Intermediate Similarity	NPD6530	Approved
0.735	Intermediate Similarity	NPD6770	Approved
0.7349	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3925	Approved
0.7333	Intermediate Similarity	NPD1467	Approved
0.7333	Intermediate Similarity	NPD1466	Phase 3
0.7333	Intermediate Similarity	NPD1505	Phase 2
0.7328	Intermediate Similarity	NPD5488	Discontinued
0.7328	Intermediate Similarity	NPD3257	Approved
0.7325	Intermediate Similarity	NPD5805	Approved
0.7319	Intermediate Similarity	NPD6242	Discontinued
0.7316	Intermediate Similarity	NPD7069	Discontinued
0.7306	Intermediate Similarity	NPD7417	Discontinued
0.7303	Intermediate Similarity	NPD4885	Approved
0.7296	Intermediate Similarity	NPD5612	Discontinued
0.7284	Intermediate Similarity	NPD3945	Discontinued
0.7284	Intermediate Similarity	NPD4454	Phase 2
0.7281	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD3003	Approved
0.728	Intermediate Similarity	NPD7994	Phase 2
0.728	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7688	Phase 1
0.7261	Intermediate Similarity	NPD4506	Discontinued
0.7257	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5902	Approved
0.7253	Intermediate Similarity	NPD5903	Approved
0.725	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7180	Phase 3
0.7243	Intermediate Similarity	NPD2951	Discontinued
0.7237	Intermediate Similarity	NPD5450	Discontinued
0.7237	Intermediate Similarity	NPD5901	Discontinued
0.7225	Intermediate Similarity	NPD2779	Approved
0.7222	Intermediate Similarity	NPD8463	Approved
0.7216	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3259	Approved
0.7205	Intermediate Similarity	NPD8091	Phase 3
0.7203	Intermediate Similarity	NPD6974	Phase 3
0.7198	Intermediate Similarity	NPD5936	Approved
0.7198	Intermediate Similarity	NPD5939	Approved
0.7197	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6550	Discontinued
0.7185	Intermediate Similarity	NPD6995	Phase 1
0.7179	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4667	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6290	Phase 2
0.7169	Intermediate Similarity	NPD8489	Phase 1
0.7167	Intermediate Similarity	NPD5866	Approved
0.7167	Intermediate Similarity	NPD3263	Phase 3
0.7154	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5658	Approved
0.7143	Intermediate Similarity	NPD4418	Discontinued
0.7117	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3986	Discontinued
0.71	Intermediate Similarity	NPD7222	Phase 2
0.7093	Intermediate Similarity	NPD2778	Approved
0.7093	Intermediate Similarity	NPD2175	Phase 3
0.7093	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD2176	Approved
0.7093	Intermediate Similarity	NPD2177	Approved
0.7092	Intermediate Similarity	NPD8358	Approved
0.7087	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD4394	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7181	Phase 3
0.7068	Intermediate Similarity	NPD7022	Phase 2
0.7067	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4368	Phase 2
0.7026	Intermediate Similarity	NPD7452	Approved
0.7026	Intermediate Similarity	NPD7453	Approved
0.7018	Intermediate Similarity	NPD3920	Phase 2
0.7018	Intermediate Similarity	NPD1768	Approved
0.7008	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD4898	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD6988	Phase 1
0.7	Intermediate Similarity	NPD5848	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD8102	Discontinued
0.6992	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD7558	Phase 2
0.6991	Remote Similarity	NPD6590	Discontinued
0.6987	Remote Similarity	NPD3289	Phase 3
0.6987	Remote Similarity	NPD3290	Approved
0.6985	Remote Similarity	NPD7925	Phase 2
0.6985	Remote Similarity	NPD7924	Phase 2
0.698	Remote Similarity	NPD5857	Phase 3
0.696	Remote Similarity	NPD6790	Phase 1
0.6958	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6958	Remote Similarity	NPD5850	Phase 3
0.6957	Remote Similarity	NPD4511	Phase 1
0.6957	Remote Similarity	NPD3328	Phase 2
0.6955	Remote Similarity	NPD7603	Discontinued
0.6949	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6985	Discontinued
0.6946	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD3354	Phase 2
0.6942	Remote Similarity	NPD7548	Discontinued
0.694	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5891	Approved
0.6933	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5913	Phase 3
0.693	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5507	Approved
0.6929	Remote Similarity	NPD5506	Approved
0.6923	Remote Similarity	NPD6494	Phase 2
0.6923	Remote Similarity	NPD6376	Discontinued
0.692	Remote Similarity	NPD3794	Approved
0.692	Remote Similarity	NPD3795	Approved
0.6917	Remote Similarity	NPD7194	Discontinued
0.6916	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4601	Approved
0.6913	Remote Similarity	NPD4501	Approved
0.6913	Remote Similarity	NPD4600	Approved
0.6913	Remote Similarity	NPD4500	Approved
0.6908	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5067	Phase 2
0.6907	Remote Similarity	NPD5066	Phase 2
0.6905	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7278	Phase 2
0.6872	Remote Similarity	NPD1038	Approved
0.6872	Remote Similarity	NPD7279	Phase 2
0.687	Remote Similarity	NPD6199	Discontinued
0.6864	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.684	Remote Similarity	NPD484	Approved
0.6838	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7470	Discontinued
0.6832	Remote Similarity	NPD5399	Discovery
0.6829	Remote Similarity	NPD5559	Phase 2
0.6822	Remote Similarity	NPD5532	Phase 2
0.682	Remote Similarity	NPD1638	Discovery
0.682	Remote Similarity	NPD4897	Phase 2
0.682	Remote Similarity	NPD6228	Discontinued
0.6818	Remote Similarity	NPD4442	Phase 2
0.6818	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1392	Approved
0.6802	Remote Similarity	NPD5924	Discontinued
0.68	Remote Similarity	NPD3250	Phase 1
0.6795	Remote Similarity	NPD3947	Discontinued
0.6789	Remote Similarity	NPD6553	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