NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	168.04
Volume:	162.983
LogP:	0.732
LogD:	0.827
LogS:	-1.587
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.644
Synthetic Accessibility Score:	2.38
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.781
MDCK Permeability:	1.1188721146027092e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.032
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.066
30% Bioavailability (F30%):	0.075

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.112
Plasma Protein Binding (PPB):	77.40142822265625%
Volume Distribution (VD):	0.596
Pgp-substrate:	17.2940616607666%

ADMET: Metabolism

CYP1A2-inhibitor:	0.834
CYP1A2-substrate:	0.759
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.659
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.247
CYP3A4-inhibitor:	0.16
CYP3A4-substrate:	0.121

ADMET: Excretion

Clearance (CL):	11.379
Half-life (T1/2):	0.893

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.019
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.102
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.154
Skin Sensitization:	0.791
Carcinogencity:	0.029
Eye Corrosion:	0.971
Eye Irritation:	0.985
Respiratory Toxicity:	0.924

Download Data

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

Natural Product: NPC237330

Natural Product ID:	NPC237330
*Common Name:**	3,5-Dihydroxy-4-Methoxybenzaldehyde
IUPAC Name:	3,5-dihydroxy-4-methoxybenzaldehyde
Synonyms:
Standard InCHIKey:	UAFQVVYJCLAIGY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H8O4/c1-12-8-6(10)2-5(4-9)3-7(8)11/h2-4,10-11H,1H3
SMILES:	COc1c(O)cc(cc1O)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL89737
PubChem CID:	12928004
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO5755.1	Bauhinia glauca	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26096681]

☑ 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	3

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3150	Individual Protein	Catechol O-methyltransferase	Rattus norvegicus	Kis	=	9.98	uM	PMID[551646]
NPT3150	Individual Protein	Catechol O-methyltransferase	Rattus norvegicus	Kii	=	16.1	uM	PMID[551646]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	20.79	%	PMID[551647]

☑ 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 NPC237330 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	373
0.1-0.2	1949
0.2-0.3	6021
0.3-0.4	12145
0.4-0.5	4495
0.5-0.6	4381
0.6-0.7	6857
0.7-0.8	5778
0.8-0.85	613
0.85-0.9	70
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9922	High Similarity	NPC274613
0.9466	High Similarity	NPC208760
0.9407	High Similarity	NPC299154
0.9375	High Similarity	NPC304747
0.9328	High Similarity	NPC4796
0.9323	High Similarity	NPC25305
0.9323	High Similarity	NPC95679
0.9323	High Similarity	NPC110899
0.9323	High Similarity	NPC112068
0.9323	High Similarity	NPC125417
0.9297	High Similarity	NPC203719
0.9297	High Similarity	NPC117237
0.9098	High Similarity	NPC155098
0.9084	High Similarity	NPC298268
0.8992	High Similarity	NPC271985
0.8986	High Similarity	NPC312256
0.8978	High Similarity	NPC50823
0.8947	High Similarity	NPC111888
0.8913	High Similarity	NPC110419
0.8889	High Similarity	NPC38101
0.8889	High Similarity	NPC139519
0.8881	High Similarity	NPC1321
0.8881	High Similarity	NPC304929
0.8881	High Similarity	NPC283823
0.8881	High Similarity	NPC159418
0.8881	High Similarity	NPC156124
0.8872	High Similarity	NPC264145
0.8857	High Similarity	NPC142165
0.8857	High Similarity	NPC207732
0.8855	High Similarity	NPC16651
0.8855	High Similarity	NPC32163
0.8806	High Similarity	NPC50763
0.8797	High Similarity	NPC299010
0.8786	High Similarity	NPC254659
0.8759	High Similarity	NPC157944
0.8759	High Similarity	NPC474274
0.875	High Similarity	NPC295317
0.875	High Similarity	NPC18646
0.8741	High Similarity	NPC288743
0.8741	High Similarity	NPC474903
0.8732	High Similarity	NPC143903
0.8732	High Similarity	NPC165389
0.8732	High Similarity	NPC226987
0.8696	High Similarity	NPC325625
0.8696	High Similarity	NPC207516
0.8692	High Similarity	NPC238810
0.8686	High Similarity	NPC156892
0.8681	High Similarity	NPC195763
0.8681	High Similarity	NPC142876
0.8681	High Similarity	NPC264289
0.8681	High Similarity	NPC333691
0.8681	High Similarity	NPC200060
0.8681	High Similarity	NPC264550
0.8681	High Similarity	NPC40290
0.8681	High Similarity	NPC69430
0.8681	High Similarity	NPC139293
0.8676	High Similarity	NPC144662
0.8671	High Similarity	NPC188074
0.8671	High Similarity	NPC125449
0.8662	High Similarity	NPC157133
0.8662	High Similarity	NPC287495
0.8662	High Similarity	NPC9370
0.8657	High Similarity	NPC285776
0.8657	High Similarity	NPC66905
0.8652	High Similarity	NPC134975
0.8652	High Similarity	NPC287722
0.8611	High Similarity	NPC203747
0.8611	High Similarity	NPC287395
0.8611	High Similarity	NPC183655
0.8611	High Similarity	NPC194653
0.8611	High Similarity	NPC254702
0.8611	High Similarity	NPC80710
0.8611	High Similarity	NPC139364
0.8592	High Similarity	NPC105213
0.8592	High Similarity	NPC275278
0.8582	High Similarity	NPC284556
0.8582	High Similarity	NPC261759
0.8582	High Similarity	NPC301178
0.8562	High Similarity	NPC75695
0.8562	High Similarity	NPC19980
0.8562	High Similarity	NPC45291
0.8562	High Similarity	NPC31363
0.8561	High Similarity	NPC58279
0.8561	High Similarity	NPC239943
0.8561	High Similarity	NPC300326
0.8552	High Similarity	NPC102003
0.8552	High Similarity	NPC92722
0.8542	High Similarity	NPC61871
0.8542	High Similarity	NPC30647
0.8542	High Similarity	NPC55557
0.8521	High Similarity	NPC471417
0.8521	High Similarity	NPC119663
0.8507	High Similarity	NPC109275
0.8503	High Similarity	NPC477231
0.8503	High Similarity	NPC105827
0.8503	High Similarity	NPC269451
0.8503	High Similarity	NPC121522
0.8503	High Similarity	NPC181209
0.8503	High Similarity	NPC291802
0.8503	High Similarity	NPC216769
0.8503	High Similarity	NPC209487
0.8503	High Similarity	NPC100971
0.8503	High Similarity	NPC131266
0.8503	High Similarity	NPC35763
0.8503	High Similarity	NPC100263
0.8503	High Similarity	NPC245382
0.8503	High Similarity	NPC257648
0.8503	High Similarity	NPC310661
0.85	High Similarity	NPC225036
0.85	High Similarity	NPC105525
0.85	High Similarity	NPC75763
0.85	High Similarity	NPC12218
0.85	High Similarity	NPC203351
0.8493	Intermediate Similarity	NPC96501
0.8493	Intermediate Similarity	NPC29231
0.8493	Intermediate Similarity	NPC472279
0.8483	Intermediate Similarity	NPC131451
0.8483	Intermediate Similarity	NPC15329
0.8472	Intermediate Similarity	NPC12377
0.8462	Intermediate Similarity	NPC242893
0.8462	Intermediate Similarity	NPC38065
0.8446	Intermediate Similarity	NPC124714
0.8446	Intermediate Similarity	NPC25127
0.8446	Intermediate Similarity	NPC287504
0.8446	Intermediate Similarity	NPC250557
0.8444	Intermediate Similarity	NPC226855
0.8444	Intermediate Similarity	NPC48315
0.8444	Intermediate Similarity	NPC8005
0.8444	Intermediate Similarity	NPC78662
0.844	Intermediate Similarity	NPC326065
0.8438	Intermediate Similarity	NPC39793
0.8435	Intermediate Similarity	NPC78505
0.8435	Intermediate Similarity	NPC256406
0.8435	Intermediate Similarity	NPC272566
0.8433	Intermediate Similarity	NPC281020
0.8433	Intermediate Similarity	NPC158654
0.8425	Intermediate Similarity	NPC134293
0.8425	Intermediate Similarity	NPC473091
0.8421	Intermediate Similarity	NPC473626
0.8414	Intermediate Similarity	NPC168803
0.8414	Intermediate Similarity	NPC77598
0.8414	Intermediate Similarity	NPC119660
0.8414	Intermediate Similarity	NPC93034
0.8403	Intermediate Similarity	NPC472917
0.8392	Intermediate Similarity	NPC469615
0.8392	Intermediate Similarity	NPC46161
0.8392	Intermediate Similarity	NPC239608
0.8389	Intermediate Similarity	NPC134287
0.8389	Intermediate Similarity	NPC130589
0.8389	Intermediate Similarity	NPC2928
0.8389	Intermediate Similarity	NPC145425
0.8389	Intermediate Similarity	NPC39184
0.8385	Intermediate Similarity	NPC229401
0.8378	Intermediate Similarity	NPC60972
0.8378	Intermediate Similarity	NPC312338
0.8378	Intermediate Similarity	NPC149889
0.8378	Intermediate Similarity	NPC39732
0.8378	Intermediate Similarity	NPC101996
0.8367	Intermediate Similarity	NPC239363
0.8367	Intermediate Similarity	NPC10467
0.8367	Intermediate Similarity	NPC156953
0.8359	Intermediate Similarity	NPC193067
0.8358	Intermediate Similarity	NPC154275
0.8356	Intermediate Similarity	NPC203077
0.8356	Intermediate Similarity	NPC272721
0.8356	Intermediate Similarity	NPC120464
0.8356	Intermediate Similarity	NPC196277
0.8356	Intermediate Similarity	NPC238279
0.8356	Intermediate Similarity	NPC107636
0.8356	Intermediate Similarity	NPC218490
0.8356	Intermediate Similarity	NPC43669
0.8356	Intermediate Similarity	NPC166036
0.8346	Intermediate Similarity	NPC145134
0.8345	Intermediate Similarity	NPC143649
0.8333	Intermediate Similarity	NPC472916
0.8333	Intermediate Similarity	NPC36490
0.8333	Intermediate Similarity	NPC469683
0.8333	Intermediate Similarity	NPC114298
0.8333	Intermediate Similarity	NPC225710
0.8322	Intermediate Similarity	NPC197188
0.8322	Intermediate Similarity	NPC88645
0.8322	Intermediate Similarity	NPC43872
0.8322	Intermediate Similarity	NPC291510
0.8322	Intermediate Similarity	NPC271779
0.8322	Intermediate Similarity	NPC281477
0.8322	Intermediate Similarity	NPC206238
0.8322	Intermediate Similarity	NPC116850
0.8322	Intermediate Similarity	NPC167091
0.8322	Intermediate Similarity	NPC292214
0.8322	Intermediate Similarity	NPC144801
0.8322	Intermediate Similarity	NPC238672
0.8322	Intermediate Similarity	NPC469550
0.8321	Intermediate Similarity	NPC158949
0.8321	Intermediate Similarity	NPC225245
0.8311	Intermediate Similarity	NPC99772
0.8311	Intermediate Similarity	NPC171010
0.8311	Intermediate Similarity	NPC262623
0.8311	Intermediate Similarity	NPC151425
0.831	Intermediate Similarity	NPC250597
0.8299	Intermediate Similarity	NPC177298

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 NPC237330 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	357
0.1-0.2	1061
0.2-0.3	2025
0.3-0.4	2774
0.4-0.5	1527
0.5-0.6	996
0.6-0.7	321
0.7-0.8	80
0.8-0.85	7
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9297	High Similarity	NPD9494	Approved
0.8881	High Similarity	NPD230	Phase 1
0.8333	Intermediate Similarity	NPD9269	Phase 2
0.8333	Intermediate Similarity	NPD3882	Suspended
0.8255	Intermediate Similarity	NPD1934	Approved
0.82	Intermediate Similarity	NPD2801	Approved
0.8092	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD1511	Approved
0.803	Intermediate Similarity	NPD9268	Approved
0.8	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD943	Approved
0.7973	Intermediate Similarity	NPD1512	Approved
0.7961	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD1510	Phase 2
0.7872	Intermediate Similarity	NPD1240	Approved
0.7862	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1465	Phase 2
0.7817	Intermediate Similarity	NPD447	Suspended
0.7786	Intermediate Similarity	NPD3027	Phase 3
0.7778	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD1607	Approved
0.775	Intermediate Similarity	NPD3818	Discontinued
0.7736	Intermediate Similarity	NPD6166	Phase 2
0.7736	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD228	Approved
0.7687	Intermediate Similarity	NPD9545	Approved
0.7682	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD3817	Phase 2
0.7619	Intermediate Similarity	NPD1549	Phase 2
0.761	Intermediate Similarity	NPD6232	Discontinued
0.7603	Intermediate Similarity	NPD1551	Phase 2
0.7593	Intermediate Similarity	NPD7054	Approved
0.7582	Intermediate Similarity	NPD824	Approved
0.7564	Intermediate Similarity	NPD5353	Approved
0.7551	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1247	Approved
0.7546	Intermediate Similarity	NPD7074	Phase 3
0.7546	Intermediate Similarity	NPD7472	Approved
0.7532	Intermediate Similarity	NPD919	Approved
0.7532	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6799	Approved
0.7483	Intermediate Similarity	NPD4357	Discontinued
0.7481	Intermediate Similarity	NPD5536	Phase 2
0.7469	Intermediate Similarity	NPD7473	Discontinued
0.7467	Intermediate Similarity	NPD6190	Approved
0.7434	Intermediate Similarity	NPD2534	Approved
0.7434	Intermediate Similarity	NPD2533	Approved
0.7434	Intermediate Similarity	NPD2532	Approved
0.741	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4628	Phase 3
0.74	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6797	Phase 2
0.7394	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1613	Approved
0.7378	Intermediate Similarity	NPD5844	Phase 1
0.7375	Intermediate Similarity	NPD5494	Approved
0.7368	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7075	Discontinued
0.7349	Intermediate Similarity	NPD7251	Discontinued
0.7343	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6234	Discontinued
0.7305	Intermediate Similarity	NPD7808	Phase 3
0.729	Intermediate Similarity	NPD1653	Approved
0.7278	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2796	Approved
0.7248	Intermediate Similarity	NPD2935	Discontinued
0.7246	Intermediate Similarity	NPD7685	Pre-registration
0.7241	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5242	Approved
0.7234	Intermediate Similarity	NPD2983	Phase 2
0.7234	Intermediate Similarity	NPD2982	Phase 2
0.7215	Intermediate Similarity	NPD37	Approved
0.7197	Intermediate Similarity	NPD6599	Discontinued
0.7181	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3750	Approved
0.717	Intermediate Similarity	NPD7819	Suspended
0.7163	Intermediate Similarity	NPD9717	Approved
0.7163	Intermediate Similarity	NPD2981	Phase 2
0.7153	Intermediate Similarity	NPD9493	Approved
0.7152	Intermediate Similarity	NPD6385	Approved
0.7152	Intermediate Similarity	NPD6386	Approved
0.7134	Intermediate Similarity	NPD3926	Phase 2
0.7121	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD920	Approved
0.7107	Intermediate Similarity	NPD6801	Discontinued
0.7105	Intermediate Similarity	NPD2800	Approved
0.7097	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4967	Phase 2
0.7081	Intermediate Similarity	NPD4965	Approved
0.7081	Intermediate Similarity	NPD4966	Approved
0.7059	Intermediate Similarity	NPD1241	Discontinued
0.7047	Intermediate Similarity	NPD6651	Approved
0.7044	Intermediate Similarity	NPD7411	Suspended
0.7041	Intermediate Similarity	NPD6559	Discontinued
0.7034	Intermediate Similarity	NPD3018	Phase 2
0.7019	Intermediate Similarity	NPD5402	Approved
0.7019	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1203	Approved
0.7012	Intermediate Similarity	NPD7199	Phase 2
0.7007	Intermediate Similarity	NPD411	Approved
0.7006	Intermediate Similarity	NPD7228	Approved
0.7	Intermediate Similarity	NPD1357	Approved
0.6993	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1358	Approved
0.6987	Remote Similarity	NPD642	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1933	Approved
0.6977	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD422	Phase 1
0.6968	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3972	Approved
0.6923	Remote Similarity	NPD1608	Approved
0.6918	Remote Similarity	NPD3455	Phase 2
0.6909	Remote Similarity	NPD6959	Discontinued
0.6908	Remote Similarity	NPD6099	Approved
0.6908	Remote Similarity	NPD6100	Approved
0.6903	Remote Similarity	NPD2219	Phase 1
0.6899	Remote Similarity	NPD5403	Approved
0.6893	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD2654	Approved
0.6883	Remote Similarity	NPD1243	Approved
0.6879	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5401	Approved
0.6871	Remote Similarity	NPD7768	Phase 2
0.6864	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD2344	Approved
0.6842	Remote Similarity	NPD3748	Approved
0.6829	Remote Similarity	NPD3749	Approved
0.6812	Remote Similarity	NPD5283	Phase 1
0.6809	Remote Similarity	NPD1548	Phase 1
0.6797	Remote Similarity	NPD9296	Approved
0.6796	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1242	Phase 1
0.6786	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD3764	Approved
0.6772	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD3146	Approved
0.677	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD5711	Approved
0.6766	Remote Similarity	NPD5710	Approved
0.6761	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7266	Discontinued
0.6736	Remote Similarity	NPD3705	Approved
0.6736	Remote Similarity	NPD1610	Phase 2
0.6735	Remote Similarity	NPD1019	Discontinued
0.6731	Remote Similarity	NPD8166	Discontinued
0.6731	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4110	Phase 3
0.6724	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1778	Approved
0.6713	Remote Similarity	NPD17	Approved
0.6712	Remote Similarity	NPD1283	Approved
0.6712	Remote Similarity	NPD1876	Approved
0.6709	Remote Similarity	NPD5297	Approved
0.6708	Remote Similarity	NPD7458	Discontinued
0.6706	Remote Similarity	NPD3751	Discontinued
0.6689	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1558	Phase 1
0.6689	Remote Similarity	NPD3620	Phase 2
0.6688	Remote Similarity	NPD2309	Approved
0.6688	Remote Similarity	NPD2354	Approved
0.6686	Remote Similarity	NPD5953	Discontinued
0.6667	Remote Similarity	NPD3134	Approved
0.6667	Remote Similarity	NPD3144	Approved
0.6667	Remote Similarity	NPD3145	Approved
0.6644	Remote Similarity	NPD4908	Phase 1
0.6644	Remote Similarity	NPD6832	Phase 2
0.6626	Remote Similarity	NPD5090	Approved
0.6626	Remote Similarity	NPD5089	Approved
0.6623	Remote Similarity	NPD2674	Phase 3
0.6623	Remote Similarity	NPD4308	Phase 3
0.6623	Remote Similarity	NPD6233	Phase 2
0.6623	Remote Similarity	NPD2799	Discontinued
0.662	Remote Similarity	NPD9092	Discovery
0.6618	Remote Similarity	NPD290	Approved
0.6617	Remote Similarity	NPD291	Approved
0.6608	Remote Similarity	NPD2163	Approved
0.6607	Remote Similarity	NPD2821	Approved
0.6606	Remote Similarity	NPD5977	Approved
0.6606	Remote Similarity	NPD5978	Approved
0.6604	Remote Similarity	NPD7390	Discontinued
0.6579	Remote Similarity	NPD3140	Approved
0.6579	Remote Similarity	NPD3142	Approved
0.6579	Remote Similarity	NPD826	Approved
0.6579	Remote Similarity	NPD825	Approved
0.6575	Remote Similarity	NPD1481	Phase 2
0.657	Remote Similarity	NPD7286	Phase 2
0.6569	Remote Similarity	NPD74	Approved
0.6569	Remote Similarity	NPD9266	Approved
0.6569	Remote Similarity	NPD2684	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