NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	241.07
Volume:	243.943
LogP:	3.247
LogD:	2.951
LogS:	-4.735
# Rotatable Bonds:	2
TPSA:	62.32
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.678
Synthetic Accessibility Score:	2.313
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.06
MDCK Permeability:	6.830996881035389e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.887

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.14
Plasma Protein Binding (PPB):	94.61492156982422%
Volume Distribution (VD):	0.669
Pgp-substrate:	4.103522300720215%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.901
CYP2C19-inhibitor:	0.365
CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.423
CYP2C9-substrate:	0.889
CYP2D6-inhibitor:	0.741
CYP2D6-substrate:	0.855
CYP3A4-inhibitor:	0.541
CYP3A4-substrate:	0.148

ADMET: Excretion

Clearance (CL):	5.126
Half-life (T1/2):	0.483

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.168
Drug-inuced Liver Injury (DILI):	0.776
AMES Toxicity:	0.412
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.823
Carcinogencity:	0.057
Eye Corrosion:	0.159
Eye Irritation:	0.985
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC179287

Natural Product ID:	NPC179287
*Common Name:**	3-Formyl-1-Hydroxy-7-Methoxycarbazole
IUPAC Name:	1-hydroxy-7-methoxy-9H-carbazole-3-carbaldehyde
Synonyms:
Standard InCHIKey:	KVGOXKTZYBQADZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H11NO3/c1-18-9-2-3-10-11-4-8(7-16)5-13(17)14(11)15-12(10)6-9/h2-7,15,17H,1H3
SMILES:	COc1ccc2c3cc(cc(c3[nH]c2c1)O)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689800
PubChem CID:	53324960
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
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	n.a.	root	n.a.	PMID[21302964]
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3236015]
NPO21978	Clausena harmandiana	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	10360.0	nM	PMID[514865]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	10690.0	nM	PMID[514865]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	179530.0	nM	PMID[514865]

☑ 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 NPC179287 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	499
0.1-0.2	3306
0.2-0.3	13397
0.3-0.4	3405
0.4-0.5	16095
0.5-0.6	3920
0.6-0.7	1533
0.7-0.8	475
0.8-0.85	25
0.85-0.9	28
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.965	High Similarity	NPC208084
0.93	High Similarity	NPC187501
0.9216	High Similarity	NPC184408
0.9216	High Similarity	NPC247803
0.9196	High Similarity	NPC249583
0.9196	High Similarity	NPC283117
0.9163	High Similarity	NPC118228
0.9126	High Similarity	NPC150239
0.9126	High Similarity	NPC225279
0.9109	High Similarity	NPC294375
0.9109	High Similarity	NPC87413
0.9073	High Similarity	NPC293151
0.902	High Similarity	NPC39500
0.8995	High Similarity	NPC51388
0.8971	High Similarity	NPC310211
0.8971	High Similarity	NPC308137
0.896	High Similarity	NPC39679
0.8937	High Similarity	NPC46561
0.8915	High Similarity	NPC274640
0.8911	High Similarity	NPC4687
0.8861	High Similarity	NPC45190
0.8857	High Similarity	NPC144452
0.8832	High Similarity	NPC474701
0.8775	High Similarity	NPC210828
0.8775	High Similarity	NPC86834
0.8762	High Similarity	NPC174760
0.8738	High Similarity	NPC23294
0.8716	High Similarity	NPC6786
0.8689	High Similarity	NPC303951
0.866	High Similarity	NPC3207
0.8657	High Similarity	NPC474688
0.8632	High Similarity	NPC198503
0.8612	High Similarity	NPC116238
0.8597	High Similarity	NPC475844
0.8585	High Similarity	NPC300156
0.8564	High Similarity	NPC128823
0.8539	High Similarity	NPC39370
0.8531	High Similarity	NPC169402
0.8447	Intermediate Similarity	NPC473186
0.8381	Intermediate Similarity	NPC9894
0.8374	Intermediate Similarity	NPC243834
0.8374	Intermediate Similarity	NPC70956
0.8373	Intermediate Similarity	NPC209769
0.8365	Intermediate Similarity	NPC321428
0.8364	Intermediate Similarity	NPC473179
0.8333	Intermediate Similarity	NPC473187
0.83	Intermediate Similarity	NPC242928
0.8297	Intermediate Similarity	NPC473188
0.819	Intermediate Similarity	NPC193777
0.8186	Intermediate Similarity	NPC131017
0.81	Intermediate Similarity	NPC473185
0.8095	Intermediate Similarity	NPC470930
0.8086	Intermediate Similarity	NPC291535
0.8086	Intermediate Similarity	NPC475085
0.8086	Intermediate Similarity	NPC475112
0.8051	Intermediate Similarity	NPC89549
0.8045	Intermediate Similarity	NPC205372
0.8037	Intermediate Similarity	NPC280799
0.802	Intermediate Similarity	NPC160381
0.8	Intermediate Similarity	NPC135887
0.8	Intermediate Similarity	NPC474798
0.8	Intermediate Similarity	NPC199277
0.7982	Intermediate Similarity	NPC194740
0.7972	Intermediate Similarity	NPC476106
0.7962	Intermediate Similarity	NPC134848
0.796	Intermediate Similarity	NPC212535
0.792	Intermediate Similarity	NPC473182
0.7917	Intermediate Similarity	NPC48353
0.79	Intermediate Similarity	NPC303658
0.7895	Intermediate Similarity	NPC306376
0.7895	Intermediate Similarity	NPC72211
0.7892	Intermediate Similarity	NPC202503
0.7882	Intermediate Similarity	NPC94943
0.7877	Intermediate Similarity	NPC162484
0.787	Intermediate Similarity	NPC146418
0.786	Intermediate Similarity	NPC325297
0.785	Intermediate Similarity	NPC183777
0.7848	Intermediate Similarity	NPC97746
0.7833	Intermediate Similarity	NPC190007
0.7828	Intermediate Similarity	NPC132642
0.7824	Intermediate Similarity	NPC199667
0.7817	Intermediate Similarity	NPC473183
0.7812	Intermediate Similarity	NPC470018
0.7807	Intermediate Similarity	NPC473184
0.7799	Intermediate Similarity	NPC70259
0.7788	Intermediate Similarity	NPC475190
0.7788	Intermediate Similarity	NPC230403
0.7778	Intermediate Similarity	NPC473181
0.7768	Intermediate Similarity	NPC208522
0.7762	Intermediate Similarity	NPC153042
0.7751	Intermediate Similarity	NPC205934
0.7751	Intermediate Similarity	NPC43787
0.7745	Intermediate Similarity	NPC84478
0.7738	Intermediate Similarity	NPC131885
0.7738	Intermediate Similarity	NPC473041
0.7725	Intermediate Similarity	NPC160100
0.7723	Intermediate Similarity	NPC88363
0.7713	Intermediate Similarity	NPC60621
0.7703	Intermediate Similarity	NPC288987
0.7675	Intermediate Similarity	NPC260434
0.7675	Intermediate Similarity	NPC477112
0.7672	Intermediate Similarity	NPC41501
0.7671	Intermediate Similarity	NPC94157
0.7671	Intermediate Similarity	NPC12344
0.7665	Intermediate Similarity	NPC471762
0.7647	Intermediate Similarity	NPC330009
0.7644	Intermediate Similarity	NPC122436
0.7642	Intermediate Similarity	NPC49547
0.7642	Intermediate Similarity	NPC132329
0.7628	Intermediate Similarity	NPC223427
0.7623	Intermediate Similarity	NPC298436
0.7621	Intermediate Similarity	NPC74575
0.7617	Intermediate Similarity	NPC267423
0.7615	Intermediate Similarity	NPC201697
0.7598	Intermediate Similarity	NPC478032
0.7598	Intermediate Similarity	NPC475253
0.7591	Intermediate Similarity	NPC473180
0.7583	Intermediate Similarity	NPC276517
0.7582	Intermediate Similarity	NPC132385
0.7576	Intermediate Similarity	NPC34770
0.7569	Intermediate Similarity	NPC475910
0.7568	Intermediate Similarity	NPC152768
0.7568	Intermediate Similarity	NPC148183
0.7563	Intermediate Similarity	NPC165964
0.756	Intermediate Similarity	NPC144381
0.7557	Intermediate Similarity	NPC89508
0.7556	Intermediate Similarity	NPC477532
0.7549	Intermediate Similarity	NPC72980
0.7546	Intermediate Similarity	NPC165599
0.7536	Intermediate Similarity	NPC42591
0.7535	Intermediate Similarity	NPC476044
0.7534	Intermediate Similarity	NPC305984
0.7534	Intermediate Similarity	NPC314552
0.7533	Intermediate Similarity	NPC21638
0.7532	Intermediate Similarity	NPC473105
0.7531	Intermediate Similarity	NPC67401
0.7525	Intermediate Similarity	NPC474409
0.7523	Intermediate Similarity	NPC16066
0.7523	Intermediate Similarity	NPC270918
0.7511	Intermediate Similarity	NPC58209
0.7511	Intermediate Similarity	NPC264176
0.7511	Intermediate Similarity	NPC252251
0.7511	Intermediate Similarity	NPC66777
0.7511	Intermediate Similarity	NPC15801
0.75	Intermediate Similarity	NPC269367
0.75	Intermediate Similarity	NPC471304
0.75	Intermediate Similarity	NPC96321
0.75	Intermediate Similarity	NPC264285
0.7489	Intermediate Similarity	NPC171787
0.7489	Intermediate Similarity	NPC470799
0.7489	Intermediate Similarity	NPC8022
0.7488	Intermediate Similarity	NPC329747
0.7479	Intermediate Similarity	NPC470784
0.7477	Intermediate Similarity	NPC471080
0.7477	Intermediate Similarity	NPC469592
0.7468	Intermediate Similarity	NPC78609
0.7468	Intermediate Similarity	NPC160898
0.7467	Intermediate Similarity	NPC140296
0.7467	Intermediate Similarity	NPC257851
0.7467	Intermediate Similarity	NPC478078
0.7467	Intermediate Similarity	NPC74360
0.7465	Intermediate Similarity	NPC476098
0.7455	Intermediate Similarity	NPC312645
0.7448	Intermediate Similarity	NPC63971
0.7448	Intermediate Similarity	NPC91868
0.7446	Intermediate Similarity	NPC477531
0.744	Intermediate Similarity	NPC176127
0.7436	Intermediate Similarity	NPC184680
0.7436	Intermediate Similarity	NPC235685
0.743	Intermediate Similarity	NPC141454
0.7429	Intermediate Similarity	NPC246700
0.7422	Intermediate Similarity	NPC174576
0.7421	Intermediate Similarity	NPC470020
0.7421	Intermediate Similarity	NPC11464
0.7416	Intermediate Similarity	NPC194040
0.7414	Intermediate Similarity	NPC474192
0.7414	Intermediate Similarity	NPC475720
0.7411	Intermediate Similarity	NPC469928
0.7409	Intermediate Similarity	NPC470931
0.7404	Intermediate Similarity	NPC101350
0.7404	Intermediate Similarity	NPC470785
0.7403	Intermediate Similarity	NPC209174
0.7397	Intermediate Similarity	NPC472287
0.7397	Intermediate Similarity	NPC472286
0.7393	Intermediate Similarity	NPC470017
0.7391	Intermediate Similarity	NPC157931
0.7387	Intermediate Similarity	NPC220337
0.7384	Intermediate Similarity	NPC166712
0.7383	Intermediate Similarity	NPC251090
0.7382	Intermediate Similarity	NPC329631
0.7377	Intermediate Similarity	NPC258048
0.7375	Intermediate Similarity	NPC270515
0.7371	Intermediate Similarity	NPC217176
0.7368	Intermediate Similarity	NPC241025
0.7364	Intermediate Similarity	NPC244741
0.7361	Intermediate Similarity	NPC18487
0.7361	Intermediate Similarity	NPC280714
0.7357	Intermediate Similarity	NPC323969
0.7354	Intermediate Similarity	NPC316981
0.7354	Intermediate Similarity	NPC219087

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 NPC179287 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	682
0.2-0.3	1014
0.3-0.4	1474
0.4-0.5	2907
0.5-0.6	1957
0.6-0.7	676
0.7-0.8	108
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8592	High Similarity	NPD6160	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD5632	Approved
0.7675	Intermediate Similarity	NPD1505	Phase 2
0.7642	Intermediate Similarity	NPD3746	Discontinued
0.7563	Intermediate Similarity	NPD3986	Discontinued
0.7534	Intermediate Similarity	NPD5164	Discontinued
0.7521	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD6242	Discontinued
0.75	Intermediate Similarity	NPD4429	Discontinued
0.75	Intermediate Similarity	NPD7395	Discontinued
0.7489	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD5479	Discontinued
0.7477	Intermediate Similarity	NPD3003	Approved
0.7468	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3259	Approved
0.7467	Intermediate Similarity	NPD3258	Approved
0.7466	Intermediate Similarity	NPD5416	Discontinued
0.7466	Intermediate Similarity	NPD4502	Phase 2
0.7465	Intermediate Similarity	NPD5512	Phase 3
0.7446	Intermediate Similarity	NPD1867	Approved
0.7443	Intermediate Similarity	NPD5429	Discontinued
0.7417	Intermediate Similarity	NPD5482	Discontinued
0.7409	Intermediate Similarity	NPD5658	Approved
0.7403	Intermediate Similarity	NPD5022	Discontinued
0.739	Intermediate Similarity	NPD8364	Approved
0.739	Intermediate Similarity	NPD8363	Approved
0.7382	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD1466	Phase 3
0.7371	Intermediate Similarity	NPD6962	Phase 2
0.7371	Intermediate Similarity	NPD1467	Approved
0.7366	Intermediate Similarity	NPD3257	Approved
0.735	Intermediate Similarity	NPD2951	Discontinued
0.7349	Intermediate Similarity	NPD5003	Discontinued
0.7342	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5612	Discontinued
0.7331	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD7853	Phase 2
0.7311	Intermediate Similarity	NPD6716	Phase 1
0.7308	Intermediate Similarity	NPD4373	Phase 2
0.7281	Intermediate Similarity	NPD1768	Approved
0.7273	Intermediate Similarity	NPD5901	Discontinued
0.7273	Intermediate Similarity	NPD7603	Discontinued
0.7269	Intermediate Similarity	NPD6790	Phase 1
0.7269	Intermediate Similarity	NPD7803	Approved
0.7261	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4952	Phase 3
0.7246	Intermediate Similarity	NPD3006	Discontinued
0.7244	Intermediate Similarity	NPD3945	Discontinued
0.7241	Intermediate Similarity	NPD4328	Approved
0.7232	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD2564	Approved
0.723	Intermediate Similarity	NPD2565	Phase 2
0.722	Intermediate Similarity	NPD5488	Discontinued
0.7217	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8465	Approved
0.7216	Intermediate Similarity	NPD8429	Approved
0.7216	Intermediate Similarity	NPD8467	Approved
0.7216	Intermediate Similarity	NPD8466	Approved
0.7216	Intermediate Similarity	NPD8427	Approved
0.7216	Intermediate Similarity	NPD8428	Approved
0.7212	Intermediate Similarity	NPD5903	Approved
0.7212	Intermediate Similarity	NPD5902	Approved
0.7209	Intermediate Similarity	NPD1038	Approved
0.7207	Intermediate Similarity	NPD7453	Approved
0.7207	Intermediate Similarity	NPD7222	Phase 2
0.7207	Intermediate Similarity	NPD7452	Approved
0.7206	Intermediate Similarity	NPD7955	Approved
0.7206	Intermediate Similarity	NPD7956	Approved
0.7202	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD8460	Approved
0.7171	Intermediate Similarity	NPD8459	Approved
0.7169	Intermediate Similarity	NPD484	Approved
0.7167	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD8091	Phase 3
0.716	Intermediate Similarity	NPD6456	Discontinued
0.7156	Intermediate Similarity	NPD5939	Approved
0.7156	Intermediate Similarity	NPD5936	Approved
0.7156	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4368	Phase 2
0.7143	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7417	Discontinued
0.7123	Intermediate Similarity	NPD2177	Approved
0.7123	Intermediate Similarity	NPD2175	Phase 3
0.7123	Intermediate Similarity	NPD2176	Approved
0.7119	Intermediate Similarity	NPD4885	Approved
0.7108	Intermediate Similarity	NPD7708	Approved
0.7104	Intermediate Similarity	NPD8425	Approved
0.7104	Intermediate Similarity	NPD2779	Approved
0.7104	Intermediate Similarity	NPD8426	Approved
0.7098	Intermediate Similarity	NPD2916	Discontinued
0.7097	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5805	Approved
0.7063	Intermediate Similarity	NPD5450	Discontinued
0.7054	Intermediate Similarity	NPD1392	Approved
0.7051	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3263	Phase 3
0.704	Intermediate Similarity	NPD6531	Approved
0.704	Intermediate Similarity	NPD6530	Approved
0.7025	Intermediate Similarity	NPD6517	Phase 3
0.7022	Intermediate Similarity	NPD6376	Discontinued
0.7021	Intermediate Similarity	NPD7994	Phase 2
0.7018	Intermediate Similarity	NPD4418	Discontinued
0.7017	Intermediate Similarity	NPD7558	Phase 2
0.6996	Remote Similarity	NPD6995	Phase 1
0.6992	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7180	Phase 3
0.6982	Remote Similarity	NPD4511	Phase 1
0.6978	Remote Similarity	NPD6290	Phase 2
0.6976	Remote Similarity	NPD8463	Approved
0.6976	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7069	Discontinued
0.697	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6985	Discontinued
0.6968	Remote Similarity	NPD2778	Approved
0.6946	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7194	Discontinued
0.694	Remote Similarity	NPD6974	Phase 3
0.694	Remote Similarity	NPD3875	Discontinued
0.6936	Remote Similarity	NPD3925	Approved
0.6933	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1325	Approved
0.6923	Remote Similarity	NPD1326	Approved
0.69	Remote Similarity	NPD5866	Approved
0.6898	Remote Similarity	NPD4948	Discontinued
0.6897	Remote Similarity	NPD3354	Phase 2
0.6889	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD4454	Phase 2
0.6886	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7948	Phase 1
0.6875	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2792	Approved
0.6864	Remote Similarity	NPD6590	Discontinued
0.6864	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD5067	Phase 2
0.6856	Remote Similarity	NPD5066	Phase 2
0.6853	Remote Similarity	NPD8244	Phase 2
0.6844	Remote Similarity	NPD2920	Discontinued
0.6842	Remote Similarity	NPD4506	Discontinued
0.6842	Remote Similarity	NPD8358	Approved
0.6838	Remote Similarity	NPD5850	Phase 3
0.6835	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7181	Phase 3
0.6827	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.682	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD3825	Phase 3
0.6815	Remote Similarity	NPD8489	Phase 1
0.6815	Remote Similarity	NPD8102	Discontinued
0.6815	Remote Similarity	NPD4558	Phase 2
0.6812	Remote Similarity	NPD3392	Approved
0.6808	Remote Similarity	NPD3920	Phase 2
0.6807	Remote Similarity	NPD4845	Discontinued
0.6805	Remote Similarity	NPD6494	Phase 2
0.6804	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5913	Phase 3
0.6797	Remote Similarity	NPD3243	Approved
0.6795	Remote Similarity	NPD6770	Approved
0.6794	Remote Similarity	NPD2844	Phase 3
0.6791	Remote Similarity	NPD8349	Phase 1
0.679	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8403	Phase 1
0.6784	Remote Similarity	NPD5399	Discovery
0.6783	Remote Similarity	NPD7470	Discontinued
0.6781	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5559	Phase 2
0.6774	Remote Similarity	NPD5256	Discontinued
0.6773	Remote Similarity	NPD5937	Approved
0.6773	Remote Similarity	NPD5532	Phase 2
0.6773	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.677	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD5293	Phase 2
0.6757	Remote Similarity	NPD6550	Discontinued
0.675	Remote Similarity	NPD5924	Discontinued
0.6749	Remote Similarity	NPD3250	Phase 1
0.6744	Remote Similarity	NPD7924	Phase 2
0.6744	Remote Similarity	NPD7925	Phase 2
0.6742	Remote Similarity	NPD4539	Phase 1
0.674	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.674	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6988	Phase 1
0.6722	Remote Similarity	NPD7688	Phase 1
0.6711	Remote Similarity	NPD3289	Phase 3
0.6711	Remote Similarity	NPD3290	Approved
0.6711	Remote Similarity	NPD5530	Phase 1
0.671	Remote Similarity	NPD6220	Phase 3
0.6707	Remote Similarity	NPD3328	Phase 2

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