NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	196.04
Volume:	186.433
LogP:	2.448
LogD:	0.862
LogS:	-2.706
# Rotatable Bonds:	2
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.611
Synthetic Accessibility Score:	2.59
Fsp3:	0.111
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:	-5.657
MDCK Permeability:	3.2456807730341097e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.422
30% Bioavailability (F30%):	0.936

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	89.76106262207031%
Volume Distribution (VD):	0.501
Pgp-substrate:	7.208649158477783%

ADMET: Metabolism

CYP1A2-inhibitor:	0.08
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.068
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.039

ADMET: Excretion

Clearance (CL):	1.726
Half-life (T1/2):	0.899

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.137
Drug-inuced Liver Injury (DILI):	0.721
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.721
Carcinogencity:	0.03
Eye Corrosion:	0.051
Eye Irritation:	0.933
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC278375

Natural Product ID:	NPC278375
*Common Name:**	Haematommic Acid
IUPAC Name:	3-formyl-2,4-dihydroxy-6-methylbenzoic acid
Synonyms:
Standard InCHIKey:	KCOOTJRKKIDHTM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H8O5/c1-4-2-6(11)5(3-10)8(12)7(4)9(13)14/h2-3,11-12H,1H3,(H,13,14)/p-1
SMILES:	Cc1cc(c(C=O)c(c1C(=O)O)O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1315277
PubChem CID:	6710680
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives

*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
NPO11504	Lethariella cladonioides	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11504	Lethariella cladonioides	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11504	Lethariella cladonioides	Species	Parmeliaceae	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
Others	2
Potency	3

Activity Type	# Activity
Individual Protein	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	19952.6	nM	PMID[473245]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	25118.9	nM	PMID[473245]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	54.98	%	PMID[473246]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	81.5	%	PMID[473246]

☑ 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 NPC278375 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	344
0.1-0.2	1671
0.2-0.3	3902
0.3-0.4	10482
0.4-0.5	8910
0.5-0.6	5069
0.6-0.7	7425
0.7-0.8	4262
0.8-0.85	464
0.85-0.9	143
0.9-0.95	19
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9624	High Similarity	NPC99441
0.9615	High Similarity	NPC474519
0.9609	High Similarity	NPC62219
0.9552	High Similarity	NPC37530
0.9538	High Similarity	NPC48036
0.9389	High Similarity	NPC37299
0.9389	High Similarity	NPC180261
0.9323	High Similarity	NPC158481
0.9318	High Similarity	NPC474394
0.9259	High Similarity	NPC162939
0.9248	High Similarity	NPC290803
0.9219	High Similarity	NPC262671
0.9219	High Similarity	NPC201728
0.9179	High Similarity	NPC118919
0.9154	High Similarity	NPC41263
0.9051	High Similarity	NPC165172
0.9051	High Similarity	NPC183345
0.9015	High Similarity	NPC247477
0.9015	High Similarity	NPC17840
0.8993	High Similarity	NPC159721
0.8971	High Similarity	NPC194579
0.8971	High Similarity	NPC178467
0.8971	High Similarity	NPC474771
0.8971	High Similarity	NPC474849
0.8971	High Similarity	NPC65837
0.8971	High Similarity	NPC149372
0.8955	High Similarity	NPC267205
0.8955	High Similarity	NPC153783
0.8947	High Similarity	NPC189823
0.8947	High Similarity	NPC219892
0.8929	High Similarity	NPC42540
0.8929	High Similarity	NPC151607
0.8921	High Similarity	NPC73061
0.8905	High Similarity	NPC475974
0.8872	High Similarity	NPC296158
0.8857	High Similarity	NPC471731
0.8849	High Similarity	NPC290550
0.8849	High Similarity	NPC470842
0.8841	High Similarity	NPC474655
0.8841	High Similarity	NPC275356
0.8841	High Similarity	NPC88269
0.8832	High Similarity	NPC70380
0.8832	High Similarity	NPC471452
0.8832	High Similarity	NPC71256
0.8806	High Similarity	NPC41847
0.8786	High Similarity	NPC471733
0.8779	High Similarity	NPC477454
0.8777	High Similarity	NPC472601
0.8777	High Similarity	NPC472600
0.8768	High Similarity	NPC177307
0.8768	High Similarity	NPC9121
0.8768	High Similarity	NPC191835
0.8768	High Similarity	NPC212693
0.8768	High Similarity	NPC472403
0.8768	High Similarity	NPC94248
0.8759	High Similarity	NPC50455
0.8759	High Similarity	NPC86524
0.8759	High Similarity	NPC191976
0.8759	High Similarity	NPC235115
0.8759	High Similarity	NPC254847
0.875	High Similarity	NPC294964
0.8741	High Similarity	NPC166583
0.8741	High Similarity	NPC53362
0.8714	High Similarity	NPC313123
0.8714	High Similarity	NPC472603
0.8714	High Similarity	NPC472604
0.8714	High Similarity	NPC204045
0.8714	High Similarity	NPC478217
0.8714	High Similarity	NPC305845
0.8714	High Similarity	NPC187843
0.8714	High Similarity	NPC472605
0.8712	High Similarity	NPC473691
0.8707	High Similarity	NPC89625
0.8707	High Similarity	NPC149618
0.8705	High Similarity	NPC139634
0.8705	High Similarity	NPC105456
0.8705	High Similarity	NPC92655
0.8705	High Similarity	NPC190457
0.8696	High Similarity	NPC53206
0.8696	High Similarity	NPC135837
0.8696	High Similarity	NPC471905
0.8696	High Similarity	NPC245058
0.8696	High Similarity	NPC53414
0.8686	High Similarity	NPC161632
0.8686	High Similarity	NPC182496
0.8686	High Similarity	NPC180905
0.8671	High Similarity	NPC163846
0.8671	High Similarity	NPC225173
0.8652	High Similarity	NPC82913
0.8652	High Similarity	NPC474961
0.8652	High Similarity	NPC135524
0.8643	High Similarity	NPC168471
0.8633	High Similarity	NPC33144
0.8633	High Similarity	NPC221104
0.8633	High Similarity	NPC478200
0.8633	High Similarity	NPC472602
0.8623	High Similarity	NPC291454
0.8623	High Similarity	NPC223836
0.8615	High Similarity	NPC215392
0.8615	High Similarity	NPC226275
0.8613	High Similarity	NPC175943
0.8613	High Similarity	NPC166480
0.8613	High Similarity	NPC282780
0.8611	High Similarity	NPC125801
0.8611	High Similarity	NPC471734
0.8601	High Similarity	NPC473692
0.8593	High Similarity	NPC147757
0.8592	High Similarity	NPC478202
0.8592	High Similarity	NPC472610
0.8592	High Similarity	NPC354984
0.8582	High Similarity	NPC1704
0.8582	High Similarity	NPC472035
0.8582	High Similarity	NPC110810
0.8582	High Similarity	NPC67650
0.8582	High Similarity	NPC478201
0.8582	High Similarity	NPC53649
0.8571	High Similarity	NPC268052
0.8571	High Similarity	NPC242994
0.8571	High Similarity	NPC138099
0.8571	High Similarity	NPC52358
0.8571	High Similarity	NPC32360
0.8571	High Similarity	NPC143438
0.8562	High Similarity	NPC119929
0.855	High Similarity	NPC91105
0.855	High Similarity	NPC218333
0.8542	High Similarity	NPC471735
0.8542	High Similarity	NPC473023
0.8538	High Similarity	NPC146642
0.8531	High Similarity	NPC21599
0.8531	High Similarity	NPC244691
0.8531	High Similarity	NPC193703
0.8531	High Similarity	NPC471906
0.8531	High Similarity	NPC48762
0.8529	High Similarity	NPC275504
0.8521	High Similarity	NPC182255
0.8521	High Similarity	NPC193555
0.8521	High Similarity	NPC94076
0.8519	High Similarity	NPC92624
0.8519	High Similarity	NPC476119
0.8516	High Similarity	NPC230349
0.8511	High Similarity	NPC181560
0.8511	High Similarity	NPC155205
0.8511	High Similarity	NPC169452
0.8511	High Similarity	NPC158472
0.8507	High Similarity	NPC209959
0.8503	High Similarity	NPC133856
0.85	High Similarity	NPC4214
0.8496	Intermediate Similarity	NPC475733
0.8493	Intermediate Similarity	NPC291049
0.8493	Intermediate Similarity	NPC233267
0.8489	Intermediate Similarity	NPC156967
0.8489	Intermediate Similarity	NPC472599
0.8485	Intermediate Similarity	NPC306288
0.8485	Intermediate Similarity	NPC472029
0.8485	Intermediate Similarity	NPC65761
0.8478	Intermediate Similarity	NPC44437
0.8478	Intermediate Similarity	NPC475645
0.8477	Intermediate Similarity	NPC143050
0.8472	Intermediate Similarity	NPC75694
0.8472	Intermediate Similarity	NPC34482
0.8467	Intermediate Similarity	NPC478190
0.8462	Intermediate Similarity	NPC84266
0.8462	Intermediate Similarity	NPC469542
0.8462	Intermediate Similarity	NPC294037
0.8462	Intermediate Similarity	NPC51106
0.8462	Intermediate Similarity	NPC472006
0.8456	Intermediate Similarity	NPC259942
0.8451	Intermediate Similarity	NPC244923
0.8451	Intermediate Similarity	NPC246638
0.8451	Intermediate Similarity	NPC90411
0.8451	Intermediate Similarity	NPC158634
0.8451	Intermediate Similarity	NPC149533
0.8451	Intermediate Similarity	NPC475730
0.845	Intermediate Similarity	NPC209486
0.845	Intermediate Similarity	NPC40649
0.8446	Intermediate Similarity	NPC271681
0.8446	Intermediate Similarity	NPC273483
0.8444	Intermediate Similarity	NPC95537
0.844	Intermediate Similarity	NPC247409
0.844	Intermediate Similarity	NPC471819
0.8433	Intermediate Similarity	NPC160499
0.8429	Intermediate Similarity	NPC53001
0.8425	Intermediate Similarity	NPC37139
0.8425	Intermediate Similarity	NPC471907
0.8425	Intermediate Similarity	NPC105415
0.8417	Intermediate Similarity	NPC475917
0.8414	Intermediate Similarity	NPC470570
0.8409	Intermediate Similarity	NPC283514
0.8409	Intermediate Similarity	NPC309765
0.8403	Intermediate Similarity	NPC210966
0.8403	Intermediate Similarity	NPC126882
0.8403	Intermediate Similarity	NPC478203
0.8397	Intermediate Similarity	NPC149246
0.8394	Intermediate Similarity	NPC85342
0.8392	Intermediate Similarity	NPC250755
0.8392	Intermediate Similarity	NPC322112
0.8392	Intermediate Similarity	NPC474385
0.8389	Intermediate Similarity	NPC208806
0.8389	Intermediate Similarity	NPC472799
0.8389	Intermediate Similarity	NPC470102

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 NPC278375 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	1030
0.2-0.3	1811
0.3-0.4	2838
0.4-0.5	1814
0.5-0.6	949
0.6-0.7	296
0.7-0.8	84
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8759	High Similarity	NPD1509	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD2533	Approved
0.8472	Intermediate Similarity	NPD2532	Approved
0.8472	Intermediate Similarity	NPD2534	Approved
0.844	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD7390	Discontinued
0.8169	Intermediate Similarity	NPD5405	Approved
0.8169	Intermediate Similarity	NPD5404	Approved
0.8169	Intermediate Similarity	NPD5408	Approved
0.8169	Intermediate Similarity	NPD5406	Approved
0.7972	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD943	Approved
0.7926	Intermediate Similarity	NPD1201	Approved
0.7908	Intermediate Similarity	NPD7819	Suspended
0.7898	Intermediate Similarity	NPD6232	Discontinued
0.7832	Intermediate Similarity	NPD1607	Approved
0.7826	Intermediate Similarity	NPD1470	Approved
0.7826	Intermediate Similarity	NPD1164	Approved
0.7793	Intermediate Similarity	NPD1551	Phase 2
0.7762	Intermediate Similarity	NPD230	Phase 1
0.775	Intermediate Similarity	NPD7473	Discontinued
0.7737	Intermediate Similarity	NPD9269	Phase 2
0.7733	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1510	Phase 2
0.7704	Intermediate Similarity	NPD9268	Approved
0.7692	Intermediate Similarity	NPD1240	Approved
0.7673	Intermediate Similarity	NPD5711	Approved
0.7673	Intermediate Similarity	NPD5710	Approved
0.7671	Intermediate Similarity	NPD2935	Discontinued
0.7612	Intermediate Similarity	NPD9493	Approved
0.761	Intermediate Similarity	NPD6959	Discontinued
0.7548	Intermediate Similarity	NPD7411	Suspended
0.7538	Intermediate Similarity	NPD74	Approved
0.7538	Intermediate Similarity	NPD9266	Approved
0.75	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9545	Approved
0.7481	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD9263	Approved
0.7462	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD9264	Approved
0.7462	Intermediate Similarity	NPD9267	Approved
0.7452	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1549	Phase 2
0.7421	Intermediate Similarity	NPD7075	Discontinued
0.7419	Intermediate Similarity	NPD3226	Approved
0.7405	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD920	Approved
0.7372	Intermediate Similarity	NPD6599	Discontinued
0.7368	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7768	Phase 2
0.7351	Intermediate Similarity	NPD3750	Approved
0.7351	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5844	Phase 1
0.7319	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1243	Approved
0.7285	Intermediate Similarity	NPD2800	Approved
0.7278	Intermediate Similarity	NPD1934	Approved
0.7273	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD919	Approved
0.7267	Intermediate Similarity	NPD2346	Discontinued
0.7266	Intermediate Similarity	NPD4626	Approved
0.7261	Intermediate Similarity	NPD4380	Phase 2
0.7254	Intermediate Similarity	NPD1283	Approved
0.7237	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6651	Approved
0.7218	Intermediate Similarity	NPD4750	Phase 3
0.7208	Intermediate Similarity	NPD1511	Approved
0.7208	Intermediate Similarity	NPD6799	Approved
0.7206	Intermediate Similarity	NPD9281	Approved
0.7205	Intermediate Similarity	NPD3749	Approved
0.7202	Intermediate Similarity	NPD6559	Discontinued
0.7192	Intermediate Similarity	NPD411	Approved
0.7171	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6801	Discontinued
0.7161	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD9261	Approved
0.7115	Intermediate Similarity	NPD1512	Approved
0.7113	Intermediate Similarity	NPD9717	Approved
0.7086	Intermediate Similarity	NPD2796	Approved
0.7081	Intermediate Similarity	NPD3817	Phase 2
0.7077	Intermediate Similarity	NPD846	Approved
0.7077	Intermediate Similarity	NPD940	Approved
0.7075	Intermediate Similarity	NPD3764	Approved
0.7075	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5691	Approved
0.7042	Intermediate Similarity	NPD1281	Approved
0.7037	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3882	Suspended
0.702	Intermediate Similarity	NPD2799	Discontinued
0.702	Intermediate Similarity	NPD3748	Approved
0.7019	Intermediate Similarity	NPD2801	Approved
0.7019	Intermediate Similarity	NPD1465	Phase 2
0.7013	Intermediate Similarity	NPD4628	Phase 3
0.7013	Intermediate Similarity	NPD7003	Approved
0.6981	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6100	Approved
0.6974	Remote Similarity	NPD6099	Approved
0.697	Remote Similarity	NPD1247	Approved
0.6966	Remote Similarity	NPD1203	Approved
0.6959	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5953	Discontinued
0.6933	Remote Similarity	NPD447	Suspended
0.6932	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3300	Phase 2
0.6923	Remote Similarity	NPD6020	Phase 2
0.6913	Remote Similarity	NPD520	Approved
0.6913	Remote Similarity	NPD6663	Approved
0.6901	Remote Similarity	NPD3019	Approved
0.6901	Remote Similarity	NPD2932	Approved
0.6897	Remote Similarity	NPD8150	Discontinued
0.689	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7458	Discontinued
0.6871	Remote Similarity	NPD9494	Approved
0.6871	Remote Similarity	NPD5736	Approved
0.6852	Remote Similarity	NPD37	Approved
0.6845	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6166	Phase 2
0.6845	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5951	Approved
0.6824	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7286	Phase 2
0.6807	Remote Similarity	NPD5494	Approved
0.6806	Remote Similarity	NPD422	Phase 1
0.6797	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3400	Discontinued
0.6784	Remote Similarity	NPD7074	Phase 3
0.6769	Remote Similarity	NPD288	Approved
0.6765	Remote Similarity	NPD3818	Discontinued
0.6759	Remote Similarity	NPD1608	Approved
0.6755	Remote Similarity	NPD2979	Phase 3
0.6747	Remote Similarity	NPD6234	Discontinued
0.6742	Remote Similarity	NPD1242	Phase 1
0.6733	Remote Similarity	NPD2313	Discontinued
0.6731	Remote Similarity	NPD2654	Approved
0.673	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4966	Approved
0.6727	Remote Similarity	NPD4965	Approved
0.6727	Remote Similarity	NPD4967	Phase 2
0.6726	Remote Similarity	NPD7229	Phase 3
0.6725	Remote Similarity	NPD7054	Approved
0.6723	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1651	Approved
0.6711	Remote Similarity	NPD6832	Phase 2
0.6711	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.671	Remote Similarity	NPD2344	Approved
0.6692	Remote Similarity	NPD844	Approved
0.6689	Remote Similarity	NPD1019	Discontinued
0.6689	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4308	Phase 3
0.6688	Remote Similarity	NPD8166	Discontinued
0.6686	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD4625	Phase 3
0.6667	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7177	Discontinued
0.6667	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8151	Discontinued
0.6647	Remote Similarity	NPD6797	Phase 2
0.6646	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5403	Approved
0.6645	Remote Similarity	NPD4060	Phase 1
0.6645	Remote Similarity	NPD2438	Suspended
0.6642	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD8312	Approved
0.6629	Remote Similarity	NPD8313	Approved
0.6625	Remote Similarity	NPD5401	Approved
0.6623	Remote Similarity	NPD3268	Approved
0.6609	Remote Similarity	NPD7251	Discontinued
0.6603	Remote Similarity	NPD1471	Phase 3
0.6603	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD6273	Approved
0.6577	Remote Similarity	NPD2798	Approved
0.6576	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6535	Approved
0.6575	Remote Similarity	NPD6534	Approved
0.6571	Remote Similarity	NPD7635	Approved
0.6571	Remote Similarity	NPD7808	Phase 3
0.6569	Remote Similarity	NPD2342	Discontinued
0.6568	Remote Similarity	NPD7199	Phase 2
0.6566	Remote Similarity	NPD4288	Approved
0.6565	Remote Similarity	NPD1809	Phase 2
0.6559	Remote Similarity	NPD7435	Discontinued
0.6556	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD17	Approved
0.6552	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD255	Approved
0.6549	Remote Similarity	NPD256	Approved
0.6541	Remote Similarity	NPD6190	Approved
0.6541	Remote Similarity	NPD2309	Approved
0.6538	Remote Similarity	NPD4476	Approved
0.6538	Remote Similarity	NPD2531	Phase 2
0.6538	Remote Similarity	NPD9570	Approved
0.6538	Remote Similarity	NPD4477	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