NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	188.05
Volume:	192.251
LogP:	3.381
LogD:	2.092
LogS:	-3.215
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.721
Synthetic Accessibility Score:	1.627
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.04
MDCK Permeability:	1.2667201190197375e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.217
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.379
Plasma Protein Binding (PPB):	95.29132843017578%
Volume Distribution (VD):	0.262
Pgp-substrate:	3.4830198287963867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.166
CYP1A2-substrate:	0.106
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.206
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.063

ADMET: Excretion

Clearance (CL):	2.306
Half-life (T1/2):	0.855

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.644
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.584
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.416
Carcinogencity:	0.348
Eye Corrosion:	0.005
Eye Irritation:	0.903
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC236189

Natural Product ID:	NPC236189
*Common Name:**	Carboxynaphthol
IUPAC Name:	1-hydroxynaphthalene-2-carboxylic acid
Synonyms:
Standard InCHIKey:	SJJCQDRGABAVBB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H8O3/c12-10-8-4-2-1-3-7(8)5-6-9(10)11(13)14/h1-6,12H,(H,13,14)
SMILES:	c1ccc2c(c1)ccc(c2O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL229299
PubChem CID:	6844
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0001871] Naphthalenecarboxylic acids and derivatives [CHEMONTID:0002421] Naphthalenecarboxylic acids

*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
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[12575075]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	stem	n.a.	PMID[12575075]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[15577255]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30188125]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29463	Pogostemon cablin	Species	Lamiaceae	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
EC50	2
IC50	4
Kd	1
Others	3

Activity Type	# Activity
Individual Protein	5
Organism	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	850000.0	nM	PMID[523539]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	>	1000000.0	nM	PMID[523540]
NPT644	Individual Protein	L-lactate dehydrogenase A chain	Homo sapiens	Kd	=	640000.0	nM	PMID[523541]
NPT644	Individual Protein	L-lactate dehydrogenase A chain	Homo sapiens	IC50	>	500000.0	nM	PMID[523541]
NPT3485	Individual Protein	Neuraminidase	Influenza A virus (strain A/Wilson-Smith/1933 H1N1) (Influenza A virus(strain A/WS/1933 H1N1))	IC50	>	100000.0	nM	PMID[523542]
NPT897	Others	Monoclonal antibody (mAb)		Log KA	=	6.708	n.a.	PMID[523538]
NPT35	Others	n.a.		LogD	=	0.16	n.a.	PMID[523540]
NPT35	Others	n.a.		LogD	=	0.25	n.a.	PMID[523540]
NPT742	Organism	Influenza A virus	Influenza A virus	EC50	>	1000000.0	nM	PMID[523540]
NPT742	Organism	Influenza A virus	Influenza A virus	EC50	>	100000.0	nM	PMID[523542]

☑ 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 NPC236189 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	395
0.1-0.2	1771
0.2-0.3	4266
0.3-0.4	11638
0.4-0.5	7430
0.5-0.6	6783
0.6-0.7	8305
0.7-0.8	1860
0.8-0.85	187
0.85-0.9	55
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9512	High Similarity	NPC31539
0.9187	High Similarity	NPC160499
0.9174	High Similarity	NPC283514
0.9174	High Similarity	NPC244351
0.9091	High Similarity	NPC198336
0.9024	High Similarity	NPC142956
0.9	High Similarity	NPC233165
0.9	High Similarity	NPC62272
0.9	High Similarity	NPC184579
0.8992	High Similarity	NPC161632
0.8992	High Similarity	NPC125252
0.8898	High Similarity	NPC31799
0.8889	High Similarity	NPC48248
0.8889	High Similarity	NPC95537
0.8871	High Similarity	NPC173978
0.8862	High Similarity	NPC307174
0.8862	High Similarity	NPC300274
0.8852	High Similarity	NPC159760
0.8852	High Similarity	NPC292665
0.8852	High Similarity	NPC222876
0.8852	High Similarity	NPC115188
0.8852	High Similarity	NPC301987
0.8852	High Similarity	NPC244994
0.8852	High Similarity	NPC35856
0.8852	High Similarity	NPC178395
0.8852	High Similarity	NPC26433
0.8852	High Similarity	NPC272454
0.8852	High Similarity	NPC179092
0.8814	High Similarity	NPC211421
0.879	High Similarity	NPC275145
0.879	High Similarity	NPC375356
0.8788	High Similarity	NPC4214
0.8779	High Similarity	NPC118919
0.8769	High Similarity	NPC288089
0.875	High Similarity	NPC55949
0.874	High Similarity	NPC282923
0.8672	High Similarity	NPC34414
0.8672	High Similarity	NPC146647
0.8657	High Similarity	NPC183345
0.8651	High Similarity	NPC103540
0.8618	High Similarity	NPC285829
0.8618	High Similarity	NPC206778
0.8607	High Similarity	NPC328694
0.8605	High Similarity	NPC136588
0.8605	High Similarity	NPC199253
0.8583	High Similarity	NPC96915
0.8571	High Similarity	NPC68756
0.8571	High Similarity	NPC152525
0.8571	High Similarity	NPC265910
0.8571	High Similarity	NPC91475
0.855	High Similarity	NPC114183
0.855	High Similarity	NPC225051
0.8548	High Similarity	NPC165197
0.8547	High Similarity	NPC318327
0.8538	High Similarity	NPC244699
0.8538	High Similarity	NPC72669
0.8538	High Similarity	NPC474517
0.8538	High Similarity	NPC205992
0.8527	High Similarity	NPC99731
0.8519	High Similarity	NPC168471
0.8512	High Similarity	NPC161304
0.8504	High Similarity	NPC240744
0.8504	High Similarity	NPC167055
0.8485	Intermediate Similarity	NPC270899
0.8485	Intermediate Similarity	NPC50924
0.8485	Intermediate Similarity	NPC12070
0.848	Intermediate Similarity	NPC25168
0.8473	Intermediate Similarity	NPC58685
0.8473	Intermediate Similarity	NPC70622
0.8467	Intermediate Similarity	NPC66593
0.8456	Intermediate Similarity	NPC290550
0.845	Intermediate Similarity	NPC96024
0.8444	Intermediate Similarity	NPC26924
0.8443	Intermediate Similarity	NPC108288
0.8443	Intermediate Similarity	NPC477453
0.8438	Intermediate Similarity	NPC3224
0.8433	Intermediate Similarity	NPC53414
0.8433	Intermediate Similarity	NPC53206
0.8425	Intermediate Similarity	NPC234890
0.8425	Intermediate Similarity	NPC74507
0.8421	Intermediate Similarity	NPC72918
0.8421	Intermediate Similarity	NPC283088
0.8421	Intermediate Similarity	NPC249272
0.8421	Intermediate Similarity	NPC290803
0.8413	Intermediate Similarity	NPC297193
0.8409	Intermediate Similarity	NPC37299
0.8409	Intermediate Similarity	NPC53896
0.8409	Intermediate Similarity	NPC115458
0.8409	Intermediate Similarity	NPC48036
0.8409	Intermediate Similarity	NPC52407
0.8409	Intermediate Similarity	NPC267205
0.8409	Intermediate Similarity	NPC180261
0.8397	Intermediate Similarity	NPC85342
0.8397	Intermediate Similarity	NPC93015
0.8397	Intermediate Similarity	NPC41847
0.839	Intermediate Similarity	NPC100551
0.8382	Intermediate Similarity	NPC315578
0.8382	Intermediate Similarity	NPC225243
0.8374	Intermediate Similarity	NPC160199
0.8372	Intermediate Similarity	NPC181715
0.8358	Intermediate Similarity	NPC254847
0.8358	Intermediate Similarity	NPC155211
0.8358	Intermediate Similarity	NPC474813
0.8346	Intermediate Similarity	NPC44437
0.8346	Intermediate Similarity	NPC282780
0.8346	Intermediate Similarity	NPC274876
0.8346	Intermediate Similarity	NPC166480
0.8346	Intermediate Similarity	NPC474394
0.8333	Intermediate Similarity	NPC66208
0.832	Intermediate Similarity	NPC7151
0.832	Intermediate Similarity	NPC233282
0.832	Intermediate Similarity	NPC473662
0.832	Intermediate Similarity	NPC216297
0.8309	Intermediate Similarity	NPC242994
0.8309	Intermediate Similarity	NPC138099
0.8306	Intermediate Similarity	NPC41567
0.8306	Intermediate Similarity	NPC184527
0.8296	Intermediate Similarity	NPC471452
0.8296	Intermediate Similarity	NPC245923
0.8296	Intermediate Similarity	NPC471905
0.8296	Intermediate Similarity	NPC53001
0.8295	Intermediate Similarity	NPC136342
0.8295	Intermediate Similarity	NPC306765
0.8295	Intermediate Similarity	NPC231774
0.8295	Intermediate Similarity	NPC295202
0.8295	Intermediate Similarity	NPC227741
0.8295	Intermediate Similarity	NPC49647
0.8293	Intermediate Similarity	NPC312800
0.8286	Intermediate Similarity	NPC314437
0.8286	Intermediate Similarity	NPC211565
0.8286	Intermediate Similarity	NPC60389
0.8284	Intermediate Similarity	NPC278375
0.8284	Intermediate Similarity	NPC80035
0.8284	Intermediate Similarity	NPC258502
0.8281	Intermediate Similarity	NPC310540
0.8281	Intermediate Similarity	NPC117794
0.8279	Intermediate Similarity	NPC186933
0.8271	Intermediate Similarity	NPC314048
0.8268	Intermediate Similarity	NPC282577
0.8254	Intermediate Similarity	NPC241001
0.8248	Intermediate Similarity	NPC169452
0.8248	Intermediate Similarity	NPC181560
0.8244	Intermediate Similarity	NPC276238
0.8244	Intermediate Similarity	NPC92624
0.8244	Intermediate Similarity	NPC109123
0.8235	Intermediate Similarity	NPC87723
0.8222	Intermediate Similarity	NPC291454
0.8222	Intermediate Similarity	NPC223836
0.8222	Intermediate Similarity	NPC272268
0.8222	Intermediate Similarity	NPC158481
0.8222	Intermediate Similarity	NPC472308
0.8222	Intermediate Similarity	NPC191976
0.8217	Intermediate Similarity	NPC472592
0.8217	Intermediate Similarity	NPC287473
0.8217	Intermediate Similarity	NPC201728
0.8217	Intermediate Similarity	NPC131799
0.8217	Intermediate Similarity	NPC262671
0.8209	Intermediate Similarity	NPC287604
0.8209	Intermediate Similarity	NPC161964
0.8209	Intermediate Similarity	NPC472262
0.8189	Intermediate Similarity	NPC120545
0.8188	Intermediate Similarity	NPC246638
0.8182	Intermediate Similarity	NPC247477
0.8182	Intermediate Similarity	NPC17840
0.8182	Intermediate Similarity	NPC205766
0.8182	Intermediate Similarity	NPC62219
0.8182	Intermediate Similarity	NPC259942
0.8182	Intermediate Similarity	NPC198305
0.8175	Intermediate Similarity	NPC190457
0.8175	Intermediate Similarity	NPC478121
0.8175	Intermediate Similarity	NPC143438
0.8162	Intermediate Similarity	NPC301915
0.8162	Intermediate Similarity	NPC261292
0.8156	Intermediate Similarity	NPC163846
0.8156	Intermediate Similarity	NPC225173
0.8154	Intermediate Similarity	NPC254492
0.8154	Intermediate Similarity	NPC8745
0.8151	Intermediate Similarity	NPC141523
0.8145	Intermediate Similarity	NPC128825
0.814	Intermediate Similarity	NPC199273
0.814	Intermediate Similarity	NPC13238
0.814	Intermediate Similarity	NPC164014
0.8136	Intermediate Similarity	NPC105899
0.8134	Intermediate Similarity	NPC472591
0.8134	Intermediate Similarity	NPC294226
0.8129	Intermediate Similarity	NPC73061
0.8129	Intermediate Similarity	NPC257644
0.8129	Intermediate Similarity	NPC193555
0.8125	Intermediate Similarity	NPC46634
0.8125	Intermediate Similarity	NPC121168
0.8125	Intermediate Similarity	NPC217756
0.8125	Intermediate Similarity	NPC176208
0.8125	Intermediate Similarity	NPC91478
0.812	Intermediate Similarity	NPC255676
0.812	Intermediate Similarity	NPC214702
0.812	Intermediate Similarity	NPC470831
0.812	Intermediate Similarity	NPC7012
0.8116	Intermediate Similarity	NPC96421
0.8112	Intermediate Similarity	NPC70764
0.811	Intermediate Similarity	NPC472046

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 NPC236189 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	961
0.2-0.3	1429
0.3-0.4	2787
0.4-0.5	2082
0.5-0.6	1058
0.6-0.7	351
0.7-0.8	74
0.8-0.85	10
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD5408	Approved
0.9	High Similarity	NPD5405	Approved
0.9	High Similarity	NPD5404	Approved
0.9	High Similarity	NPD5406	Approved
0.8952	High Similarity	NPD1164	Approved
0.878	High Similarity	NPD1201	Approved
0.8651	High Similarity	NPD1470	Approved
0.8443	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.839	Intermediate Similarity	NPD9266	Approved
0.839	Intermediate Similarity	NPD74	Approved
0.8358	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8305	Intermediate Similarity	NPD9263	Approved
0.8305	Intermediate Similarity	NPD9267	Approved
0.8305	Intermediate Similarity	NPD9264	Approved
0.8235	Intermediate Similarity	NPD2346	Discontinued
0.8162	Intermediate Similarity	NPD2935	Discontinued
0.8145	Intermediate Similarity	NPD9493	Approved
0.7984	Intermediate Similarity	NPD5951	Approved
0.7966	Intermediate Similarity	NPD9261	Approved
0.7939	Intermediate Similarity	NPD1203	Approved
0.7887	Intermediate Similarity	NPD7390	Discontinued
0.7863	Intermediate Similarity	NPD1283	Approved
0.7851	Intermediate Similarity	NPD2342	Discontinued
0.784	Intermediate Similarity	NPD9281	Approved
0.7794	Intermediate Similarity	NPD943	Approved
0.7778	Intermediate Similarity	NPD2313	Discontinued
0.774	Intermediate Similarity	NPD3226	Approved
0.774	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7635	Approved
0.7676	Intermediate Similarity	NPD7003	Approved
0.7647	Intermediate Similarity	NPD411	Approved
0.7643	Intermediate Similarity	NPD1551	Phase 2
0.7634	Intermediate Similarity	NPD1281	Approved
0.7615	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD9717	Approved
0.7571	Intermediate Similarity	NPD2799	Discontinued
0.7554	Intermediate Similarity	NPD1607	Approved
0.7535	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6232	Discontinued
0.7521	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD1930	Approved
0.7521	Intermediate Similarity	NPD1929	Approved
0.7518	Intermediate Similarity	NPD3764	Approved
0.7481	Intermediate Similarity	NPD2798	Approved
0.7466	Intermediate Similarity	NPD2532	Approved
0.7466	Intermediate Similarity	NPD2534	Approved
0.7466	Intermediate Similarity	NPD2533	Approved
0.7447	Intermediate Similarity	NPD4308	Phase 3
0.7447	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1932	Approved
0.7431	Intermediate Similarity	NPD3750	Approved
0.7419	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7819	Suspended
0.741	Intermediate Similarity	NPD1240	Approved
0.7405	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7473	Discontinued
0.736	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD447	Suspended
0.7348	Intermediate Similarity	NPD3019	Approved
0.7348	Intermediate Similarity	NPD4626	Approved
0.7348	Intermediate Similarity	NPD2932	Approved
0.7338	Intermediate Similarity	NPD520	Approved
0.7329	Intermediate Similarity	NPD3300	Phase 2
0.7324	Intermediate Similarity	NPD1510	Phase 2
0.7319	Intermediate Similarity	NPD7008	Discontinued
0.7279	Intermediate Similarity	NPD2797	Approved
0.7273	Intermediate Similarity	NPD1651	Approved
0.7265	Intermediate Similarity	NPD1239	Approved
0.725	Intermediate Similarity	NPD288	Approved
0.7246	Intermediate Similarity	NPD6832	Phase 2
0.7234	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2344	Approved
0.7208	Intermediate Similarity	NPD7768	Phase 2
0.7203	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD9258	Approved
0.7179	Intermediate Similarity	NPD9256	Approved
0.7177	Intermediate Similarity	NPD1237	Approved
0.7167	Intermediate Similarity	NPD844	Approved
0.7163	Intermediate Similarity	NPD4307	Phase 2
0.7161	Intermediate Similarity	NPD3749	Approved
0.7143	Intermediate Similarity	NPD1202	Approved
0.7143	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD2066	Phase 3
0.7111	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1611	Approved
0.7092	Intermediate Similarity	NPD6663	Approved
0.7087	Intermediate Similarity	NPD2329	Discontinued
0.7083	Intermediate Similarity	NPD3748	Approved
0.7075	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1196	Approved
0.7075	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD9545	Approved
0.7059	Intermediate Similarity	NPD1608	Approved
0.7059	Intermediate Similarity	NPD9269	Phase 2
0.7055	Intermediate Similarity	NPD1549	Phase 2
0.705	Intermediate Similarity	NPD5736	Approved
0.7047	Intermediate Similarity	NPD1543	Discontinued
0.7042	Intermediate Similarity	NPD2979	Phase 3
0.7031	Intermediate Similarity	NPD4750	Phase 3
0.7027	Intermediate Similarity	NPD2309	Approved
0.7025	Intermediate Similarity	NPD6959	Discontinued
0.7023	Intermediate Similarity	NPD497	Approved
0.7021	Intermediate Similarity	NPD3268	Approved
0.7015	Intermediate Similarity	NPD9268	Approved
0.7015	Intermediate Similarity	NPD5691	Approved
0.7007	Intermediate Similarity	NPD1243	Approved
0.7007	Intermediate Similarity	NPD1195	Approved
0.7007	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD845	Approved
0.7	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5844	Phase 1
0.697	Remote Similarity	NPD8313	Approved
0.697	Remote Similarity	NPD8312	Approved
0.6967	Remote Similarity	NPD1564	Approved
0.6967	Remote Similarity	NPD1565	Approved
0.6967	Remote Similarity	NPD1566	Phase 3
0.6963	Remote Similarity	NPD2286	Discontinued
0.6959	Remote Similarity	NPD3400	Discontinued
0.6954	Remote Similarity	NPD6273	Approved
0.695	Remote Similarity	NPD4625	Phase 3
0.6948	Remote Similarity	NPD7411	Suspended
0.6947	Remote Similarity	NPD495	Approved
0.6947	Remote Similarity	NPD496	Approved
0.6947	Remote Similarity	NPD498	Approved
0.6946	Remote Similarity	NPD8150	Discontinued
0.6943	Remote Similarity	NPD7075	Discontinued
0.694	Remote Similarity	NPD1759	Phase 1
0.6935	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1511	Approved
0.6928	Remote Similarity	NPD7458	Discontinued
0.6918	Remote Similarity	NPD2438	Suspended
0.6894	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4380	Phase 2
0.6883	Remote Similarity	NPD6599	Discontinued
0.6875	Remote Similarity	NPD5710	Approved
0.6875	Remote Similarity	NPD1933	Approved
0.6875	Remote Similarity	NPD5711	Approved
0.6871	Remote Similarity	NPD1471	Phase 3
0.6867	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1758	Phase 1
0.6859	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1465	Phase 2
0.6857	Remote Similarity	NPD1019	Discontinued
0.6857	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1238	Approved
0.6855	Remote Similarity	NPD3020	Approved
0.6848	Remote Similarity	NPD6559	Discontinued
0.6846	Remote Similarity	NPD4628	Phase 3
0.6846	Remote Similarity	NPD8166	Discontinued
0.6842	Remote Similarity	NPD1512	Approved
0.6838	Remote Similarity	NPD9259	Approved
0.6838	Remote Similarity	NPD17	Approved
0.6838	Remote Similarity	NPD9257	Approved
0.6835	Remote Similarity	NPD1876	Approved
0.6812	Remote Similarity	NPD3972	Approved
0.6812	Remote Similarity	NPD4878	Approved
0.681	Remote Similarity	NPD7177	Discontinued
0.6806	Remote Similarity	NPD4060	Phase 1
0.6803	Remote Similarity	NPD2531	Phase 2
0.6803	Remote Similarity	NPD4477	Approved
0.6803	Remote Similarity	NPD4476	Approved
0.68	Remote Similarity	NPD1242	Phase 1
0.6794	Remote Similarity	NPD9508	Approved
0.6791	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3023	Approved
0.6788	Remote Similarity	NPD3026	Approved
0.6786	Remote Similarity	NPD3267	Approved
0.6786	Remote Similarity	NPD3266	Approved
0.6784	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD9279	Approved
0.6776	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD164	Approved
0.6768	Remote Similarity	NPD6020	Phase 2
0.6765	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3024	Approved
0.6765	Remote Similarity	NPD3025	Approved
0.6759	Remote Similarity	NPD230	Phase 1
0.675	Remote Similarity	NPD1089	Approved
0.675	Remote Similarity	NPD1090	Approved
0.675	Remote Similarity	NPD1086	Approved
0.6748	Remote Similarity	NPD2859	Approved
0.6748	Remote Similarity	NPD2860	Approved
0.6748	Remote Similarity	NPD1809	Phase 2
0.6721	Remote Similarity	NPD1563	Approved
0.6718	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD256	Approved
0.6716	Remote Similarity	NPD255	Approved
0.6714	Remote Similarity	NPD3225	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