NPASS Compound

Structure

NPC469412 OpenBabel07101719402D 24 25 0 0 1 0 0 0 0 0999 V2000 -7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 2 3 2 0 0 0 0 3 8 1 0 0 0 0 4 6 1 0 0 0 0 4 11 2 0 0 0 0 5 7 2 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 7 12 1 0 0 0 0 8 22 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 12 22 1 0 0 0 0 13 9 1 6 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 1 0 0 0 15 16 1 0 0 0 0 15 20 1 6 0 0 0 16 17 1 0 0 0 0 16 21 1 1 0 0 0 17 23 1 6 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.14
Volume:	333.825
LogP:	0.761
LogD:	0.889
LogS:	-1.665
# Rotatable Bonds:	7
TPSA:	108.61
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.507
Synthetic Accessibility Score:	3.828
Fsp3:	0.471
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.124
MDCK Permeability:	2.424518061161507e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.389
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.193
Plasma Protein Binding (PPB):	48.45111083984375%
Volume Distribution (VD):	0.639
Pgp-substrate:	43.34246063232422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.496
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.101
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.233
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.097

ADMET: Excretion

Clearance (CL):	2.032
Half-life (T1/2):	0.689

ADMET: Toxicity

hERG Blockers:	0.145
Human Hepatotoxicity (H-HT):	0.122
Drug-inuced Liver Injury (DILI):	0.142
AMES Toxicity:	0.595
Rat Oral Acute Toxicity:	0.148
Maximum Recommended Daily Dose:	0.049
Skin Sensitization:	0.932
Carcinogencity:	0.837
Eye Corrosion:	0.003
Eye Irritation:	0.119
Respiratory Toxicity:	0.286

Download Data

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

Natural Product: NPC469412

Natural Product ID:	NPC469412
*Common Name:**	Terricollene A
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[(4-buta-2,3-dienoxyphenyl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	PLHYONMLZLAVMD-NQNKBUKLSA-N
Standard InCHI:	InChI=1S/C17H22O7/c1-2-3-8-22-12-6-4-11(5-7-12)10-23-17-16(21)15(20)14(19)13(9-18)24-17/h3-7,13-21H,1,8-10H2/t13-,14-,15+,16-,17-/m1/s1
SMILES:	C=C=CCOc1ccc(cc1)CO[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078078
PubChem CID:	46882749
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO1743	Neurospora terricola	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19795843]
NPO1743	Neurospora terricola	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	53300.0	nM	PMID[489847]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	59200.0	nM	PMID[489847]

☑ 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 NPC469412 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	328
0.1-0.2	1439
0.2-0.3	4273
0.3-0.4	10997
0.4-0.5	7561
0.5-0.6	6535
0.6-0.7	8703
0.7-0.8	2480
0.8-0.85	279
0.85-0.9	74
0.9-0.95	22
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC198734
0.9825	High Similarity	NPC269242
0.9737	High Similarity	NPC60589
0.9737	High Similarity	NPC469708
0.9492	High Similarity	NPC287429
0.9487	High Similarity	NPC476142
0.9402	High Similarity	NPC226712
0.9262	High Similarity	NPC270849
0.9262	High Similarity	NPC26653
0.925	High Similarity	NPC470510
0.9217	High Similarity	NPC175771
0.9187	High Similarity	NPC472024
0.9187	High Similarity	NPC80600
0.918	High Similarity	NPC302378
0.9113	High Similarity	NPC9912
0.9106	High Similarity	NPC248355
0.9106	High Similarity	NPC166040
0.9106	High Similarity	NPC295970
0.9098	High Similarity	NPC198798
0.9043	High Similarity	NPC313193
0.9032	High Similarity	NPC474491
0.8968	High Similarity	NPC25821
0.896	High Similarity	NPC121376
0.8952	High Similarity	NPC97326
0.8898	High Similarity	NPC476411
0.8898	High Similarity	NPC187194
0.8898	High Similarity	NPC471029
0.8889	High Similarity	NPC26080
0.8889	High Similarity	NPC162093
0.8889	High Similarity	NPC85799
0.8889	High Similarity	NPC165686
0.8889	High Similarity	NPC303422
0.8889	High Similarity	NPC148055
0.8879	High Similarity	NPC157338
0.8871	High Similarity	NPC146540
0.8871	High Similarity	NPC40377
0.8828	High Similarity	NPC79957
0.8819	High Similarity	NPC49074
0.8819	High Similarity	NPC115022
0.8819	High Similarity	NPC294166
0.8819	High Similarity	NPC69513
0.8819	High Similarity	NPC215833
0.881	High Similarity	NPC65942
0.881	High Similarity	NPC248307
0.88	High Similarity	NPC307110
0.88	High Similarity	NPC218003
0.878	High Similarity	NPC12308
0.876	High Similarity	NPC166180
0.875	High Similarity	NPC251981
0.875	High Similarity	NPC130496
0.875	High Similarity	NPC188555
0.875	High Similarity	NPC13745
0.875	High Similarity	NPC48863
0.874	High Similarity	NPC299144
0.873	High Similarity	NPC262606
0.8718	High Similarity	NPC142319
0.8692	High Similarity	NPC138738
0.8692	High Similarity	NPC262328
0.8692	High Similarity	NPC87777
0.8692	High Similarity	NPC470413
0.8682	High Similarity	NPC470236
0.8682	High Similarity	NPC55040
0.8682	High Similarity	NPC238243
0.8672	High Similarity	NPC6836
0.8661	High Similarity	NPC166168
0.8618	High Similarity	NPC212176
0.8615	High Similarity	NPC37468
0.8615	High Similarity	NPC103409
0.8615	High Similarity	NPC242028
0.8615	High Similarity	NPC40664
0.8615	High Similarity	NPC3293
0.8615	High Similarity	NPC164857
0.8615	High Similarity	NPC165482
0.8615	High Similarity	NPC138350
0.8615	High Similarity	NPC197723
0.8615	High Similarity	NPC203230
0.8605	High Similarity	NPC87696
0.8605	High Similarity	NPC35731
0.8605	High Similarity	NPC34456
0.8605	High Similarity	NPC470881
0.8595	High Similarity	NPC469702
0.8595	High Similarity	NPC282409
0.8594	High Similarity	NPC269421
0.8594	High Similarity	NPC252833
0.8584	High Similarity	NPC37714
0.8584	High Similarity	NPC152384
0.8583	High Similarity	NPC228907
0.8561	High Similarity	NPC106944
0.855	High Similarity	NPC59324
0.855	High Similarity	NPC124149
0.855	High Similarity	NPC65530
0.8538	High Similarity	NPC212729
0.8537	High Similarity	NPC52097
0.8534	High Similarity	NPC46844
0.8527	High Similarity	NPC132895
0.8525	High Similarity	NPC476448
0.8525	High Similarity	NPC201402
0.8525	High Similarity	NPC469703
0.8525	High Similarity	NPC476445
0.8525	High Similarity	NPC160854
0.8525	High Similarity	NPC469704
0.8525	High Similarity	NPC469548
0.8516	High Similarity	NPC475067
0.85	High Similarity	NPC9248
0.8496	Intermediate Similarity	NPC215512
0.8496	Intermediate Similarity	NPC186406
0.8496	Intermediate Similarity	NPC80098
0.8496	Intermediate Similarity	NPC210192
0.8496	Intermediate Similarity	NPC76871
0.8496	Intermediate Similarity	NPC108674
0.8496	Intermediate Similarity	NPC469661
0.8496	Intermediate Similarity	NPC476442
0.8485	Intermediate Similarity	NPC212770
0.8485	Intermediate Similarity	NPC100389
0.8485	Intermediate Similarity	NPC98777
0.8475	Intermediate Similarity	NPC301735
0.8473	Intermediate Similarity	NPC475628
0.8473	Intermediate Similarity	NPC172818
0.8473	Intermediate Similarity	NPC294470
0.8473	Intermediate Similarity	NPC52277
0.8473	Intermediate Similarity	NPC186418
0.8473	Intermediate Similarity	NPC25695
0.8473	Intermediate Similarity	NPC104167
0.8473	Intermediate Similarity	NPC177035
0.8473	Intermediate Similarity	NPC469383
0.8473	Intermediate Similarity	NPC199459
0.8462	Intermediate Similarity	NPC107478
0.8455	Intermediate Similarity	NPC11724
0.8455	Intermediate Similarity	NPC55608
0.8455	Intermediate Similarity	NPC469686
0.845	Intermediate Similarity	NPC470270
0.8448	Intermediate Similarity	NPC474148
0.8448	Intermediate Similarity	NPC276061
0.8433	Intermediate Similarity	NPC469559
0.8433	Intermediate Similarity	NPC189115
0.8433	Intermediate Similarity	NPC128337
0.8433	Intermediate Similarity	NPC84207
0.8433	Intermediate Similarity	NPC5253
0.8433	Intermediate Similarity	NPC49542
0.8433	Intermediate Similarity	NPC139976
0.8433	Intermediate Similarity	NPC475084
0.8433	Intermediate Similarity	NPC230718
0.8433	Intermediate Similarity	NPC145319
0.8433	Intermediate Similarity	NPC472353
0.8433	Intermediate Similarity	NPC246947
0.8433	Intermediate Similarity	NPC60249
0.8425	Intermediate Similarity	NPC72529
0.8421	Intermediate Similarity	NPC195814
0.8421	Intermediate Similarity	NPC210478
0.8421	Intermediate Similarity	NPC202700
0.8421	Intermediate Similarity	NPC8302
0.8417	Intermediate Similarity	NPC301651
0.8417	Intermediate Similarity	NPC473556
0.8409	Intermediate Similarity	NPC36434
0.8409	Intermediate Similarity	NPC304152
0.8409	Intermediate Similarity	NPC134260
0.84	Intermediate Similarity	NPC94276
0.84	Intermediate Similarity	NPC109822
0.8397	Intermediate Similarity	NPC185778
0.839	Intermediate Similarity	NPC115379
0.8387	Intermediate Similarity	NPC471067
0.8387	Intermediate Similarity	NPC71090
0.8385	Intermediate Similarity	NPC215037
0.8376	Intermediate Similarity	NPC30563
0.8376	Intermediate Similarity	NPC264784
0.8374	Intermediate Similarity	NPC476872
0.837	Intermediate Similarity	NPC185307
0.837	Intermediate Similarity	NPC469367
0.837	Intermediate Similarity	NPC478239
0.837	Intermediate Similarity	NPC473044
0.837	Intermediate Similarity	NPC116922
0.837	Intermediate Similarity	NPC46092
0.837	Intermediate Similarity	NPC470950
0.837	Intermediate Similarity	NPC252169
0.8359	Intermediate Similarity	NPC86030
0.8359	Intermediate Similarity	NPC5851
0.8358	Intermediate Similarity	NPC273932
0.8358	Intermediate Similarity	NPC79908
0.8358	Intermediate Similarity	NPC89686
0.8358	Intermediate Similarity	NPC257095
0.8346	Intermediate Similarity	NPC147821
0.8346	Intermediate Similarity	NPC298821
0.8346	Intermediate Similarity	NPC319625
0.8346	Intermediate Similarity	NPC183181
0.8346	Intermediate Similarity	NPC288416
0.8346	Intermediate Similarity	NPC111247
0.8346	Intermediate Similarity	NPC163332
0.8346	Intermediate Similarity	NPC156376
0.8346	Intermediate Similarity	NPC292056
0.8346	Intermediate Similarity	NPC118787
0.8346	Intermediate Similarity	NPC41706
0.8333	Intermediate Similarity	NPC157554
0.8333	Intermediate Similarity	NPC83218
0.8333	Intermediate Similarity	NPC167571
0.8333	Intermediate Similarity	NPC207179
0.8333	Intermediate Similarity	NPC278552
0.8333	Intermediate Similarity	NPC126991
0.832	Intermediate Similarity	NPC232454
0.832	Intermediate Similarity	NPC470907
0.832	Intermediate Similarity	NPC178449

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 NPC469412 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	275
0.1-0.2	819
0.2-0.3	1798
0.3-0.4	2785
0.4-0.5	1735
0.5-0.6	1062
0.6-0.7	609
0.7-0.8	63
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9402	High Similarity	NPD1091	Approved
0.8362	Intermediate Similarity	NPD2684	Approved
0.8276	Intermediate Similarity	NPD290	Approved
0.8235	Intermediate Similarity	NPD7843	Approved
0.8043	Intermediate Similarity	NPD5058	Phase 3
0.8033	Intermediate Similarity	NPD7157	Approved
0.7895	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1613	Approved
0.7887	Intermediate Similarity	NPD1653	Approved
0.7874	Intermediate Similarity	NPD3705	Approved
0.7852	Intermediate Similarity	NPD4536	Approved
0.7852	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD4538	Approved
0.7826	Intermediate Similarity	NPD6674	Discontinued
0.7803	Intermediate Similarity	NPD3027	Phase 3
0.7794	Intermediate Similarity	NPD5960	Phase 3
0.7794	Intermediate Similarity	NPD5588	Approved
0.7778	Intermediate Similarity	NPD1357	Approved
0.7752	Intermediate Similarity	NPD3685	Discontinued
0.774	Intermediate Similarity	NPD8455	Phase 2
0.7731	Intermediate Similarity	NPD968	Approved
0.7717	Intermediate Similarity	NPD5846	Approved
0.7717	Intermediate Similarity	NPD6516	Phase 2
0.7698	Intermediate Similarity	NPD1652	Phase 2
0.7698	Intermediate Similarity	NPD1548	Phase 1
0.7692	Intermediate Similarity	NPD8651	Approved
0.7687	Intermediate Similarity	NPD6233	Phase 2
0.7681	Intermediate Similarity	NPD7266	Discontinued
0.7669	Intermediate Similarity	NPD3179	Approved
0.7669	Intermediate Similarity	NPD3180	Approved
0.7652	Intermediate Similarity	NPD2861	Phase 2
0.7597	Intermediate Similarity	NPD1610	Phase 2
0.7594	Intermediate Similarity	NPD4908	Phase 1
0.7594	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD7097	Phase 1
0.7584	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD291	Approved
0.7522	Intermediate Similarity	NPD9365	Approved
0.7521	Intermediate Similarity	NPD1358	Approved
0.7519	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD821	Approved
0.7481	Intermediate Similarity	NPD6798	Discontinued
0.7481	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD4340	Discontinued
0.7442	Intermediate Similarity	NPD5125	Phase 3
0.7442	Intermediate Similarity	NPD5126	Approved
0.7426	Intermediate Similarity	NPD4062	Phase 3
0.7398	Intermediate Similarity	NPD556	Approved
0.7394	Intermediate Similarity	NPD4628	Phase 3
0.7376	Intermediate Similarity	NPD2424	Discontinued
0.736	Intermediate Similarity	NPD5535	Approved
0.7328	Intermediate Similarity	NPD422	Phase 1
0.7323	Intermediate Similarity	NPD6671	Approved
0.7319	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD5124	Phase 1
0.7319	Intermediate Similarity	NPD6355	Discontinued
0.7295	Intermediate Similarity	NPD3134	Approved
0.7287	Intermediate Similarity	NPD1894	Discontinued
0.728	Intermediate Similarity	NPD228	Approved
0.728	Intermediate Similarity	NPD969	Suspended
0.7273	Intermediate Similarity	NPD4535	Phase 3
0.7273	Intermediate Similarity	NPD2231	Phase 2
0.7273	Intermediate Similarity	NPD2235	Phase 2
0.7266	Intermediate Similarity	NPD6653	Approved
0.7246	Intermediate Similarity	NPD4060	Phase 1
0.7239	Intermediate Similarity	NPD1820	Approved
0.7239	Intermediate Similarity	NPD1817	Approved
0.7239	Intermediate Similarity	NPD1819	Approved
0.7239	Intermediate Similarity	NPD1818	Approved
0.7222	Intermediate Similarity	NPD2677	Approved
0.7194	Intermediate Similarity	NPD5735	Approved
0.7183	Intermediate Similarity	NPD5763	Approved
0.7183	Intermediate Similarity	NPD5762	Approved
0.7183	Intermediate Similarity	NPD1375	Discontinued
0.7176	Intermediate Similarity	NPD1778	Approved
0.7165	Intermediate Similarity	NPD5283	Phase 1
0.7163	Intermediate Similarity	NPD7033	Discontinued
0.7163	Intermediate Similarity	NPD4108	Discontinued
0.7153	Intermediate Similarity	NPD3165	Approved
0.7153	Intermediate Similarity	NPD3166	Approved
0.7153	Intermediate Similarity	NPD3164	Approved
0.7153	Intermediate Similarity	NPD3167	Approved
0.7153	Intermediate Similarity	NPD7095	Approved
0.7152	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7054	Approved
0.7122	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD3496	Discontinued
0.7111	Intermediate Similarity	NPD6362	Approved
0.7107	Intermediate Similarity	NPD7074	Phase 3
0.7107	Intermediate Similarity	NPD7472	Approved
0.7101	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD9552	Approved
0.7092	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6582	Phase 2
0.709	Intermediate Similarity	NPD2982	Phase 2
0.709	Intermediate Similarity	NPD6583	Phase 3
0.709	Intermediate Similarity	NPD4749	Approved
0.709	Intermediate Similarity	NPD2983	Phase 2
0.7089	Intermediate Similarity	NPD3818	Discontinued
0.7075	Intermediate Similarity	NPD3536	Discontinued
0.7068	Intermediate Similarity	NPD1535	Discovery
0.7063	Intermediate Similarity	NPD6797	Phase 2
0.7059	Intermediate Similarity	NPD3691	Phase 2
0.7059	Intermediate Similarity	NPD558	Phase 2
0.7059	Intermediate Similarity	NPD3690	Phase 2
0.7059	Intermediate Similarity	NPD5647	Approved
0.7055	Intermediate Similarity	NPD5756	Phase 2
0.7054	Intermediate Similarity	NPD191	Approved
0.7051	Intermediate Similarity	NPD3787	Discontinued
0.705	Intermediate Similarity	NPD1423	Approved
0.7037	Intermediate Similarity	NPD3225	Approved
0.7031	Intermediate Similarity	NPD1241	Discontinued
0.7023	Intermediate Similarity	NPD1182	Approved
0.7021	Intermediate Similarity	NPD3052	Approved
0.7021	Intermediate Similarity	NPD3054	Approved
0.7019	Intermediate Similarity	NPD6559	Discontinued
0.7019	Intermediate Similarity	NPD7251	Discontinued
0.7015	Intermediate Similarity	NPD2981	Phase 2
0.7015	Intermediate Similarity	NPD1481	Phase 2
0.7007	Intermediate Similarity	NPD6799	Approved
0.7007	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3018	Phase 2
0.7	Intermediate Similarity	NPD3596	Phase 2
0.7	Intermediate Similarity	NPD4140	Approved
0.6993	Remote Similarity	NPD2240	Approved
0.6993	Remote Similarity	NPD2239	Approved
0.6992	Remote Similarity	NPD3847	Discontinued
0.6987	Remote Similarity	NPD7199	Phase 2
0.6985	Remote Similarity	NPD1794	Approved
0.6984	Remote Similarity	NPD5451	Approved
0.6978	Remote Similarity	NPD1048	Approved
0.6975	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7808	Phase 3
0.6974	Remote Similarity	NPD37	Approved
0.697	Remote Similarity	NPD5585	Approved
0.697	Remote Similarity	NPD6382	Discontinued
0.6966	Remote Similarity	NPD4237	Approved
0.6966	Remote Similarity	NPD4236	Phase 3
0.6963	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4380	Phase 2
0.6953	Remote Similarity	NPD1138	Approved
0.6948	Remote Similarity	NPD4965	Approved
0.6948	Remote Similarity	NPD4966	Approved
0.6948	Remote Similarity	NPD4967	Phase 2
0.6944	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6005	Phase 3
0.6944	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6004	Phase 3
0.6944	Remote Similarity	NPD521	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6002	Phase 3
0.6944	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.694	Remote Similarity	NPD776	Approved
0.6935	Remote Similarity	NPD9697	Approved
0.6934	Remote Similarity	NPD6584	Phase 3
0.6933	Remote Similarity	NPD3686	Approved
0.6933	Remote Similarity	NPD3687	Approved
0.6929	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2978	Approved
0.6928	Remote Similarity	NPD2977	Approved
0.6928	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5163	Phase 2
0.6906	Remote Similarity	NPD4625	Phase 3
0.6897	Remote Similarity	NPD1549	Phase 2
0.6897	Remote Similarity	NPD5958	Discontinued
0.6897	Remote Similarity	NPD4534	Discontinued
0.6894	Remote Similarity	NPD6581	Approved
0.6894	Remote Similarity	NPD6580	Approved
0.6892	Remote Similarity	NPD7212	Phase 2
0.6892	Remote Similarity	NPD1774	Approved
0.6892	Remote Similarity	NPD7213	Phase 3
0.6891	Remote Similarity	NPD2934	Approved
0.6891	Remote Similarity	NPD2933	Approved
0.6889	Remote Similarity	NPD1608	Approved
0.6879	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1558	Phase 1
0.6879	Remote Similarity	NPD2238	Phase 2
0.6875	Remote Similarity	NPD6032	Approved
0.6875	Remote Similarity	NPD7228	Approved
0.6875	Remote Similarity	NPD1139	Approved
0.6875	Remote Similarity	NPD1137	Approved
0.6867	Remote Similarity	NPD5403	Approved
0.6863	Remote Similarity	NPD1934	Approved
0.6861	Remote Similarity	NPD987	Approved
0.6859	Remote Similarity	NPD6234	Discontinued
0.6857	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD9501	Approved
0.6852	Remote Similarity	NPD7007	Discovery
0.6849	Remote Similarity	NPD5062	Approved
0.6849	Remote Similarity	NPD4162	Approved
0.6849	Remote Similarity	NPD5061	Approved
0.6849	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4123	Phase 3
0.6846	Remote Similarity	NPD6419	Discontinued
0.6846	Remote Similarity	NPD5401	Approved
0.6846	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4868	Clinical (unspecified phase)

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