NPASS Compound

Structure

CID293151 OpenBabel06191716102D 21 23 0 0 0 0 0 0 0 0999 V2000 1.6759 -4.8389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3518 -4.8392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5145 -1.4515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5143 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6767 -1.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6763 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5141 -3.3877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6763 -2.9038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5147 -0.4843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3523 -1.9365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 -4.3553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5145 -1.4525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6765 -1.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8382 -1.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8380 -0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6768 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 -1.4522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8383 -0.4840 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 4.3199 -1.9367 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6772 0.9997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 2 0 0 0 0 6 15 2 0 0 0 0 7 8 1 0 0 0 0 7 11 2 0 0 0 0 8 13 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 10 20 2 0 0 0 0 12 13 1 0 0 0 0 13 17 2 0 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 15 19 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	279.13
Volume:	301.7
LogP:	5.223
LogD:	3.882
LogS:	-4.054
# Rotatable Bonds:	3
TPSA:	53.09
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.553
Synthetic Accessibility Score:	2.73
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.992
MDCK Permeability:	1.1017977158189751e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.865
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.3
Plasma Protein Binding (PPB):	96.30184936523438%
Volume Distribution (VD):	1.407
Pgp-substrate:	2.4649658203125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.988
CYP1A2-substrate:	0.215
CYP2C19-inhibitor:	0.92
CYP2C19-substrate:	0.08
CYP2C9-inhibitor:	0.853
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.81
CYP2D6-substrate:	0.637
CYP3A4-inhibitor:	0.459
CYP3A4-substrate:	0.125

ADMET: Excretion

Clearance (CL):	5.069
Half-life (T1/2):	0.312

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.671
Drug-inuced Liver Injury (DILI):	0.578
AMES Toxicity:	0.174
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.76
Skin Sensitization:	0.937
Carcinogencity:	0.328
Eye Corrosion:	0.065
Eye Irritation:	0.967
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC293151

Natural Product ID:	NPC293151
*Common Name:**	Clausine-D
IUPAC Name:	1-hydroxy-4-(3-methylbut-2-enyl)-9H-carbazole-3-carbaldehyde
Synonyms:	Clausine-D
Standard InCHIKey:	PNBKXALRNLUCJB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H17NO2/c1-11(2)7-8-13-12(10-20)9-16(21)18-17(13)14-5-3-4-6-15(14)19-18/h3-7,9-10,19,21H,8H2,1-2H3
SMILES:	O=Cc1cc(O)c2c(c1CC=C(C)C)c1ccccc1[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2036044
PubChem CID:	3035740
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
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000023]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19327990]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	Stems	n.a.	n.a.	PMID[22372931]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24798144]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26523463]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23546	Clausena lansium	Species	Rutaceae	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	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[470783]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2000.0	nM	PMID[470783]

☑ 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 NPC293151 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	409
0.1-0.2	2825
0.2-0.3	12974
0.3-0.4	4982
0.4-0.5	16150
0.5-0.6	3227
0.6-0.7	1811
0.7-0.8	276
0.8-0.85	22
0.85-0.9	12
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9531	High Similarity	NPC283117
0.9403	High Similarity	NPC51388
0.9337	High Similarity	NPC294375
0.9254	High Similarity	NPC225279
0.9141	High Similarity	NPC9894
0.913	High Similarity	NPC474701
0.9073	High Similarity	NPC179287
0.9005	High Similarity	NPC118228
0.8942	High Similarity	NPC274640
0.8883	High Similarity	NPC144452
0.8856	High Similarity	NPC187501
0.8762	High Similarity	NPC23294
0.8738	High Similarity	NPC208084
0.8713	High Similarity	NPC303951
0.8689	High Similarity	NPC184408
0.8679	High Similarity	NPC474688
0.8618	High Similarity	NPC475844
0.8614	High Similarity	NPC210828
0.8614	High Similarity	NPC86834
0.8495	Intermediate Similarity	NPC39500
0.8431	Intermediate Similarity	NPC39679
0.8429	Intermediate Similarity	NPC150239
0.8333	Intermediate Similarity	NPC247803
0.8333	Intermediate Similarity	NPC45190
0.8311	Intermediate Similarity	NPC6786
0.8293	Intermediate Similarity	NPC249583
0.8221	Intermediate Similarity	NPC87413
0.8219	Intermediate Similarity	NPC39370
0.8211	Intermediate Similarity	NPC473186
0.8152	Intermediate Similarity	NPC3207
0.8131	Intermediate Similarity	NPC246700
0.8119	Intermediate Similarity	NPC153042
0.8095	Intermediate Similarity	NPC308137
0.8095	Intermediate Similarity	NPC310211
0.8075	Intermediate Similarity	NPC46561
0.8068	Intermediate Similarity	NPC300156
0.8047	Intermediate Similarity	NPC280799
0.8039	Intermediate Similarity	NPC128823
0.8029	Intermediate Similarity	NPC4687
0.8	Intermediate Similarity	NPC477112
0.7963	Intermediate Similarity	NPC198503
0.795	Intermediate Similarity	NPC128751
0.7917	Intermediate Similarity	NPC174760
0.7915	Intermediate Similarity	NPC199667
0.791	Intermediate Similarity	NPC469497
0.791	Intermediate Similarity	NPC106833
0.7908	Intermediate Similarity	NPC88363
0.7889	Intermediate Similarity	NPC94943
0.7883	Intermediate Similarity	NPC132329
0.7867	Intermediate Similarity	NPC473181
0.7861	Intermediate Similarity	NPC242928
0.7857	Intermediate Similarity	NPC193777
0.7857	Intermediate Similarity	NPC321428
0.785	Intermediate Similarity	NPC160381
0.7839	Intermediate Similarity	NPC190007
0.7799	Intermediate Similarity	NPC134848
0.7789	Intermediate Similarity	NPC212535
0.7778	Intermediate Similarity	NPC314552
0.7778	Intermediate Similarity	NPC169402
0.7778	Intermediate Similarity	NPC478032
0.7773	Intermediate Similarity	NPC208522
0.7767	Intermediate Similarity	NPC116238
0.7754	Intermediate Similarity	NPC89549
0.7738	Intermediate Similarity	NPC470018
0.7729	Intermediate Similarity	NPC306376
0.7707	Intermediate Similarity	NPC230403
0.7706	Intermediate Similarity	NPC473179
0.77	Intermediate Similarity	NPC209769
0.77	Intermediate Similarity	NPC325297
0.7699	Intermediate Similarity	NPC473187
0.7696	Intermediate Similarity	NPC160898
0.7689	Intermediate Similarity	NPC183777
0.7689	Intermediate Similarity	NPC270918
0.7682	Intermediate Similarity	NPC473188
0.7681	Intermediate Similarity	NPC243834
0.7681	Intermediate Similarity	NPC70956
0.7674	Intermediate Similarity	NPC473180
0.767	Intermediate Similarity	NPC276517
0.7653	Intermediate Similarity	NPC171787
0.7647	Intermediate Similarity	NPC144381
0.7644	Intermediate Similarity	NPC49547
0.763	Intermediate Similarity	NPC476098
0.763	Intermediate Similarity	NPC165599
0.7611	Intermediate Similarity	NPC473182
0.7598	Intermediate Similarity	NPC221873
0.7596	Intermediate Similarity	NPC141454
0.7593	Intermediate Similarity	NPC48353
0.7578	Intermediate Similarity	NPC202503
0.7569	Intermediate Similarity	NPC469928
0.7569	Intermediate Similarity	NPC330009
0.7569	Intermediate Similarity	NPC322064
0.7562	Intermediate Similarity	NPC474798
0.7558	Intermediate Similarity	NPC31700
0.7552	Intermediate Similarity	NPC76982
0.7545	Intermediate Similarity	NPC74575
0.7537	Intermediate Similarity	NPC241025
0.7523	Intermediate Similarity	NPC53344
0.7512	Intermediate Similarity	NPC12344
0.7512	Intermediate Similarity	NPC219087
0.7511	Intermediate Similarity	NPC276657
0.7511	Intermediate Similarity	NPC15801
0.7511	Intermediate Similarity	NPC132642
0.7489	Intermediate Similarity	NPC74969
0.7489	Intermediate Similarity	NPC205372
0.7488	Intermediate Similarity	NPC213308
0.7476	Intermediate Similarity	NPC472284
0.7467	Intermediate Similarity	NPC473185
0.7452	Intermediate Similarity	NPC475190
0.7442	Intermediate Similarity	NPC244741
0.7441	Intermediate Similarity	NPC476167
0.743	Intermediate Similarity	NPC470930
0.7421	Intermediate Similarity	NPC264285
0.7418	Intermediate Similarity	NPC475112
0.7418	Intermediate Similarity	NPC475085
0.7418	Intermediate Similarity	NPC291535
0.7404	Intermediate Similarity	NPC99666
0.7393	Intermediate Similarity	NPC192315
0.7391	Intermediate Similarity	NPC83111
0.7384	Intermediate Similarity	NPC67401
0.7379	Intermediate Similarity	NPC206186
0.7376	Intermediate Similarity	NPC312645
0.7376	Intermediate Similarity	NPC72980
0.7375	Intermediate Similarity	NPC475746
0.7357	Intermediate Similarity	NPC194740
0.7352	Intermediate Similarity	NPC94157
0.7352	Intermediate Similarity	NPC110182
0.735	Intermediate Similarity	NPC474409
0.7333	Intermediate Similarity	NPC131017
0.7333	Intermediate Similarity	NPC181502
0.7333	Intermediate Similarity	NPC85066
0.733	Intermediate Similarity	NPC194040
0.7327	Intermediate Similarity	NPC477111
0.7324	Intermediate Similarity	NPC45459
0.7324	Intermediate Similarity	NPC315491
0.7318	Intermediate Similarity	NPC89508
0.7316	Intermediate Similarity	NPC470017
0.7315	Intermediate Similarity	NPC472286
0.7315	Intermediate Similarity	NPC476106
0.7315	Intermediate Similarity	NPC472287
0.7313	Intermediate Similarity	NPC303225
0.7309	Intermediate Similarity	NPC288987
0.7304	Intermediate Similarity	NPC284888
0.7302	Intermediate Similarity	NPC223427
0.7297	Intermediate Similarity	NPC27041
0.7297	Intermediate Similarity	NPC472285
0.7296	Intermediate Similarity	NPC41501
0.7295	Intermediate Similarity	NPC132385
0.7294	Intermediate Similarity	NPC201697
0.7281	Intermediate Similarity	NPC88008
0.7277	Intermediate Similarity	NPC280714
0.7273	Intermediate Similarity	NPC294620
0.7269	Intermediate Similarity	NPC214142
0.7269	Intermediate Similarity	NPC24370
0.7269	Intermediate Similarity	NPC319232
0.7265	Intermediate Similarity	NPC303658
0.726	Intermediate Similarity	NPC470020
0.726	Intermediate Similarity	NPC309845
0.7241	Intermediate Similarity	NPC477549
0.7238	Intermediate Similarity	NPC181081
0.7238	Intermediate Similarity	NPC473800
0.7237	Intermediate Similarity	NPC124920
0.7237	Intermediate Similarity	NPC118559
0.7237	Intermediate Similarity	NPC34580
0.7237	Intermediate Similarity	NPC261251
0.7237	Intermediate Similarity	NPC304307
0.7235	Intermediate Similarity	NPC175602
0.7232	Intermediate Similarity	NPC74360
0.7232	Intermediate Similarity	NPC269270
0.723	Intermediate Similarity	NPC473747
0.723	Intermediate Similarity	NPC72211
0.7222	Intermediate Similarity	NPC162484
0.7215	Intermediate Similarity	NPC61038
0.7212	Intermediate Similarity	NPC220851
0.7212	Intermediate Similarity	NPC16352
0.721	Intermediate Similarity	NPC473183
0.7205	Intermediate Similarity	NPC252251
0.7205	Intermediate Similarity	NPC100547
0.72	Intermediate Similarity	NPC14686
0.7198	Intermediate Similarity	NPC473184
0.7198	Intermediate Similarity	NPC476319
0.7195	Intermediate Similarity	NPC474428
0.719	Intermediate Similarity	NPC472589
0.7189	Intermediate Similarity	NPC132539
0.7188	Intermediate Similarity	NPC131885
0.7183	Intermediate Similarity	NPC156704
0.7182	Intermediate Similarity	NPC471304
0.7182	Intermediate Similarity	NPC5145
0.7178	Intermediate Similarity	NPC472588
0.7178	Intermediate Similarity	NPC34508
0.7176	Intermediate Similarity	NPC199277
0.7176	Intermediate Similarity	NPC135887
0.7175	Intermediate Similarity	NPC477110
0.7174	Intermediate Similarity	NPC322135
0.7174	Intermediate Similarity	NPC223409
0.7174	Intermediate Similarity	NPC95240
0.7168	Intermediate Similarity	NPC473317
0.7163	Intermediate Similarity	NPC314573
0.7163	Intermediate Similarity	NPC249040
0.7162	Intermediate Similarity	NPC257851
0.7162	Intermediate Similarity	NPC478078

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 NPC293151 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	689
0.2-0.3	913
0.3-0.4	1407
0.4-0.5	3119
0.5-0.6	2023
0.6-0.7	647
0.7-0.8	61
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8263	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.8211	Intermediate Similarity	NPD3746	Discontinued
0.7877	Intermediate Similarity	NPD5939	Approved
0.7877	Intermediate Similarity	NPD5936	Approved
0.7864	Intermediate Similarity	NPD2175	Phase 3
0.7864	Intermediate Similarity	NPD2177	Approved
0.7864	Intermediate Similarity	NPD2176	Approved
0.7778	Intermediate Similarity	NPD5164	Discontinued
0.7703	Intermediate Similarity	NPD4511	Phase 1
0.7606	Intermediate Similarity	NPD6290	Phase 2
0.7594	Intermediate Similarity	NPD5901	Discontinued
0.7583	Intermediate Similarity	NPD6456	Discontinued
0.757	Intermediate Similarity	NPD6376	Discontinued
0.7564	Intermediate Similarity	NPD3986	Discontinued
0.7546	Intermediate Similarity	NPD4502	Phase 2
0.7533	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7603	Discontinued
0.743	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7395	Discontinued
0.7361	Intermediate Similarity	NPD5429	Discontinued
0.7346	Intermediate Similarity	NPD5003	Discontinued
0.7342	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD5479	Discontinued
0.7324	Intermediate Similarity	NPD484	Approved
0.7273	Intermediate Similarity	NPD2951	Discontinued
0.7265	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD4429	Discontinued
0.725	Intermediate Similarity	NPD1326	Approved
0.725	Intermediate Similarity	NPD1325	Approved
0.7248	Intermediate Similarity	NPD2916	Discontinued
0.7235	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6716	Phase 1
0.7225	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD2565	Phase 2
0.7225	Intermediate Similarity	NPD2564	Approved
0.7217	Intermediate Similarity	NPD5512	Phase 3
0.7217	Intermediate Similarity	NPD1867	Approved
0.7212	Intermediate Similarity	NPD6995	Phase 1
0.7207	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6242	Discontinued
0.7198	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3809	Discontinued
0.7189	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5632	Approved
0.7186	Intermediate Similarity	NPD5151	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD7948	Phase 1
0.7175	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5022	Discontinued
0.7156	Intermediate Similarity	NPD3258	Approved
0.7155	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD5416	Discontinued
0.7143	Intermediate Similarity	NPD2920	Discontinued
0.7137	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4948	Discontinued
0.7123	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2844	Phase 3
0.7101	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD4561	Discontinued
0.7073	Intermediate Similarity	NPD6159	Phase 2
0.7069	Intermediate Similarity	NPD1505	Phase 2
0.7038	Intermediate Similarity	NPD8349	Phase 1
0.7026	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD6162	Approved
0.7023	Intermediate Similarity	NPD6161	Approved
0.7022	Intermediate Similarity	NPD5612	Discontinued
0.7021	Intermediate Similarity	NPD7853	Phase 2
0.702	Intermediate Similarity	NPD7181	Phase 3
0.7013	Intermediate Similarity	NPD4845	Discontinued
0.7009	Intermediate Similarity	NPD3945	Discontinued
0.7009	Intermediate Similarity	NPD3243	Approved
0.6996	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3257	Approved
0.6967	Remote Similarity	NPD2383	Phase 1
0.6959	Remote Similarity	NPD8396	Approved
0.6959	Remote Similarity	NPD8395	Approved
0.6957	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3006	Discontinued
0.694	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.694	Remote Similarity	NPD4328	Approved
0.6938	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1534	Approved
0.6933	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5488	Discontinued
0.6927	Remote Similarity	NPD4601	Approved
0.6927	Remote Similarity	NPD4600	Approved
0.6923	Remote Similarity	NPD7688	Phase 1
0.6923	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1467	Approved
0.6923	Remote Similarity	NPD1466	Phase 3
0.6905	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3263	Phase 3
0.6895	Remote Similarity	NPD6530	Approved
0.6895	Remote Similarity	NPD7708	Approved
0.6895	Remote Similarity	NPD6531	Approved
0.6892	Remote Similarity	NPD7452	Approved
0.6892	Remote Similarity	NPD7222	Phase 2
0.6892	Remote Similarity	NPD7453	Approved
0.689	Remote Similarity	NPD3178	Discontinued
0.6887	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3259	Approved
0.6857	Remote Similarity	NPD3319	Phase 1
0.6857	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3320	Approved
0.6857	Remote Similarity	NPD3318	Approved
0.6856	Remote Similarity	NPD6770	Approved
0.6853	Remote Similarity	NPD3925	Approved
0.6852	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD3003	Approved
0.6844	Remote Similarity	NPD5482	Discontinued
0.6842	Remote Similarity	NPD5445	Approved
0.6838	Remote Similarity	NPD8364	Approved
0.6838	Remote Similarity	NPD8363	Approved
0.6833	Remote Similarity	NPD7417	Discontinued
0.6822	Remote Similarity	NPD4885	Approved
0.6814	Remote Similarity	NPD7454	Approved
0.6814	Remote Similarity	NPD7455	Approved
0.6814	Remote Similarity	NPD8093	Discontinued
0.6814	Remote Similarity	NPD2794	Discontinued
0.6812	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD1038	Approved
0.6805	Remote Similarity	NPD6517	Phase 3
0.6804	Remote Similarity	NPD3814	Phase 1
0.68	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7726	Phase 1
0.6795	Remote Similarity	NPD7994	Phase 2
0.6794	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5913	Phase 3
0.6787	Remote Similarity	NPD6975	Discontinued
0.6787	Remote Similarity	NPD2779	Approved
0.6786	Remote Similarity	NPD5658	Approved
0.6786	Remote Similarity	NPD7803	Approved
0.6784	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6962	Phase 2
0.6778	Remote Similarity	NPD5805	Approved
0.6774	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7470	Discontinued
0.6759	Remote Similarity	NPD5937	Approved
0.6758	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6176	Phase 1
0.6757	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD4506	Discontinued
0.6754	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD1685	Approved
0.6749	Remote Similarity	NPD1684	Approved
0.6748	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD8091	Phase 3
0.6743	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.674	Remote Similarity	NPD7069	Discontinued
0.674	Remote Similarity	NPD3330	Phase 1
0.6736	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7924	Phase 2
0.6732	Remote Similarity	NPD7925	Phase 2
0.6731	Remote Similarity	NPD9690	Approved
0.6726	Remote Similarity	NPD6987	Phase 1
0.6726	Remote Similarity	NPD5426	Phase 3
0.6723	Remote Similarity	NPD4373	Phase 2
0.672	Remote Similarity	NPD7955	Approved
0.672	Remote Similarity	NPD7956	Approved
0.6715	Remote Similarity	NPD3776	Discontinued
0.6713	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.671	Remote Similarity	NPD6974	Phase 3
0.6699	Remote Similarity	NPD5021	Discontinued
0.6697	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4418	Discontinued
0.6696	Remote Similarity	NPD7001	Phase 3
0.6694	Remote Similarity	NPD6790	Phase 1
0.6681	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.668	Remote Similarity	NPD3962	Phase 2
0.668	Remote Similarity	NPD3959	Phase 2
0.668	Remote Similarity	NPD8467	Approved
0.668	Remote Similarity	NPD8428	Approved
0.668	Remote Similarity	NPD8429	Approved
0.668	Remote Similarity	NPD8427	Approved
0.668	Remote Similarity	NPD8466	Approved
0.668	Remote Similarity	NPD8465	Approved
0.6667	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3684	Discontinued
0.6667	Remote Similarity	NPD4454	Phase 2
0.6667	Remote Similarity	NPD7878	Phase 2
0.6667	Remote Similarity	NPD4952	Phase 3
0.6652	Remote Similarity	NPD5507	Approved
0.6652	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD2778	Approved
0.6652	Remote Similarity	NPD5506	Approved
0.6652	Remote Similarity	NPD3947	Discontinued
0.6651	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD8460	Approved
0.6641	Remote Similarity	NPD8459	Approved
0.664	Remote Similarity	NPD8244	Phase 2
0.6638	Remote Similarity	NPD4312	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data