NPASS Compound

Structure

NPC229894 OpenBabel07101718322D 30 32 0 0 1 0 0 0 0 0999 V2000 -4.8193 1.8625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0440 0.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6015 0.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4051 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3710 0.1895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6980 -0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 -5.0781 0.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 0.8660 0.5000 0.0000 C 0 0 2 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 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 18 1 0 0 0 0 3 19 2 0 0 0 0 6 8 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 12 1 0 0 0 0 9 19 1 0 0 0 0 10 11 2 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 26 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 19 22 1 0 0 0 0 20 25 1 0 0 0 0 21 23 2 0 0 0 0 22 27 1 1 0 0 0 23 28 1 0 0 0 0 24 26 1 1 0 0 0 24 27 1 0 0 0 0 25 29 2 0 0 0 0 25 30 1 0 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.28
Volume:	460.431
LogP:	6.551
LogD:	4.991
LogS:	-4.263
# Rotatable Bonds:	7
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.469
Synthetic Accessibility Score:	4.164
Fsp3:	0.593
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.17
MDCK Permeability:	1.884855555545073e-05
Pgp-inhibitor:	0.173
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.914
30% Bioavailability (F30%):	0.047

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	95.66755676269531%
Volume Distribution (VD):	0.282
Pgp-substrate:	1.9769165515899658%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.618
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.1
CYP2C9-inhibitor:	0.181
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.3
CYP2D6-substrate:	0.167
CYP3A4-inhibitor:	0.153
CYP3A4-substrate:	0.096

ADMET: Excretion

Clearance (CL):	2.026
Half-life (T1/2):	0.506

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.579
Drug-inuced Liver Injury (DILI):	0.818
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.569
Skin Sensitization:	0.103
Carcinogencity:	0.035
Eye Corrosion:	0.007
Eye Irritation:	0.569
Respiratory Toxicity:	0.669

Download Data

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

Natural Product: NPC229894

Natural Product ID:	NPC229894
*Common Name:**	(+)-Isojaspic Acid
IUPAC Name:	3-[[(1R,4aR,5S,8aS)-5,8a-dimethyl-2-methylidene-5-(4-methylpent-4-enyl)-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-4-hydroxybenzoic acid
Synonyms:	(+)-Isojaspic Acid
Standard InCHIKey:	VTVMRXMYDVQASV-CIOIWQPASA-N
Standard InCHI:	InChI=1S/C27H38O3/c1-18(2)8-6-13-26(4)14-7-15-27(5)22(19(3)9-12-24(26)27)17-21-16-20(25(29)30)10-11-23(21)28/h10-11,16,22,24,28H,1,3,6-9,12-15,17H2,2,4-5H3,(H,29,30)/t22-,24-,26+,27+/m1/s1
SMILES:	C=C(C)CCC[C@@]1(C)CCC[C@@]2(C)[C@H](Cc3cc(ccc3O)C(=O)O)C(=C)CC[C@H]12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL223870
PubChem CID:	16215552
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO32440	Cacospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11720537]
NPO32440	Cacospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17346077]

☑ 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
MIC	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	2.5	ug.mL-1	PMID[496033]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	400.0	ug.mL-1	PMID[496033]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	400.0	ug.mL-1	PMID[496033]

☑ 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 NPC229894 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	307
0.1-0.2	1374
0.2-0.3	2349
0.3-0.4	6419
0.4-0.5	11296
0.5-0.6	7645
0.6-0.7	10030
0.7-0.8	3117
0.8-0.85	127
0.85-0.9	20
0.9-0.95	9
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9758	High Similarity	NPC18798
0.9756	High Similarity	NPC117899
0.9675	High Similarity	NPC193203
0.9528	High Similarity	NPC477594
0.9453	High Similarity	NPC477596
0.9426	High Similarity	NPC174991
0.9308	High Similarity	NPC477592
0.9237	High Similarity	NPC477593
0.9091	High Similarity	NPC273282
0.9091	High Similarity	NPC474890
0.9091	High Similarity	NPC161943
0.903	High Similarity	NPC477595
0.8976	High Similarity	NPC84672
0.8976	High Similarity	NPC78364
0.8976	High Similarity	NPC176130
0.8976	High Similarity	NPC69424
0.8926	High Similarity	NPC83718
0.8837	High Similarity	NPC276238
0.8828	High Similarity	NPC72667
0.8769	High Similarity	NPC108129
0.875	High Similarity	NPC254492
0.8702	High Similarity	NPC471851
0.8692	High Similarity	NPC171460
0.8692	High Similarity	NPC303910
0.8672	High Similarity	NPC137416
0.8651	High Similarity	NPC162935
0.8651	High Similarity	NPC249340
0.8633	High Similarity	NPC75295
0.8623	High Similarity	NPC271451
0.8615	High Similarity	NPC3009
0.8615	High Similarity	NPC96024
0.8605	High Similarity	NPC473751
0.8594	High Similarity	NPC199273
0.8583	High Similarity	NPC475192
0.8583	High Similarity	NPC67300
0.8571	High Similarity	NPC164852
0.8571	High Similarity	NPC241001
0.8571	High Similarity	NPC49742
0.8571	High Similarity	NPC78307
0.8571	High Similarity	NPC477139
0.856	High Similarity	NPC42657
0.8537	High Similarity	NPC322197
0.8525	High Similarity	NPC242136
0.8516	High Similarity	NPC275145
0.8507	High Similarity	NPC202225
0.8507	High Similarity	NPC475088
0.85	High Similarity	NPC258856
0.845	Intermediate Similarity	NPC184219
0.8438	Intermediate Similarity	NPC121168
0.8438	Intermediate Similarity	NPC282577
0.8433	Intermediate Similarity	NPC111845
0.8425	Intermediate Similarity	NPC216216
0.8421	Intermediate Similarity	NPC476847
0.8406	Intermediate Similarity	NPC172311
0.84	Intermediate Similarity	NPC174087
0.8394	Intermediate Similarity	NPC473622
0.8385	Intermediate Similarity	NPC137750
0.8382	Intermediate Similarity	NPC118919
0.838	Intermediate Similarity	NPC5568
0.838	Intermediate Similarity	NPC477483
0.838	Intermediate Similarity	NPC325032
0.837	Intermediate Similarity	NPC293454
0.8359	Intermediate Similarity	NPC154696
0.8359	Intermediate Similarity	NPC295034
0.8358	Intermediate Similarity	NPC175738
0.8357	Intermediate Similarity	NPC100242
0.8346	Intermediate Similarity	NPC247477
0.8346	Intermediate Similarity	NPC17840
0.8333	Intermediate Similarity	NPC473744
0.8333	Intermediate Similarity	NPC473017
0.8322	Intermediate Similarity	NPC17600
0.8322	Intermediate Similarity	NPC279442
0.8321	Intermediate Similarity	NPC204579
0.8321	Intermediate Similarity	NPC475957
0.8321	Intermediate Similarity	NPC53001
0.8321	Intermediate Similarity	NPC62952
0.8309	Intermediate Similarity	NPC290803
0.8309	Intermediate Similarity	NPC153088
0.8296	Intermediate Similarity	NPC475457
0.8296	Intermediate Similarity	NPC138472
0.8296	Intermediate Similarity	NPC180261
0.8296	Intermediate Similarity	NPC475627
0.8296	Intermediate Similarity	NPC475346
0.8296	Intermediate Similarity	NPC18982
0.8296	Intermediate Similarity	NPC37299
0.8295	Intermediate Similarity	NPC176208
0.8286	Intermediate Similarity	NPC477209
0.8286	Intermediate Similarity	NPC184935
0.8281	Intermediate Similarity	NPC259703
0.8281	Intermediate Similarity	NPC32322
0.8276	Intermediate Similarity	NPC124842
0.8273	Intermediate Similarity	NPC315578
0.8273	Intermediate Similarity	NPC181560
0.8273	Intermediate Similarity	NPC169452
0.8273	Intermediate Similarity	NPC471853
0.8273	Intermediate Similarity	NPC470986
0.8271	Intermediate Similarity	NPC99731
0.8271	Intermediate Similarity	NPC474998
0.8268	Intermediate Similarity	NPC473767
0.8264	Intermediate Similarity	NPC52931
0.8264	Intermediate Similarity	NPC327962
0.8264	Intermediate Similarity	NPC470039
0.8264	Intermediate Similarity	NPC142654
0.8261	Intermediate Similarity	NPC4214
0.8261	Intermediate Similarity	NPC87723
0.8261	Intermediate Similarity	NPC230811
0.8258	Intermediate Similarity	NPC100067
0.8258	Intermediate Similarity	NPC116513
0.8258	Intermediate Similarity	NPC103356
0.8258	Intermediate Similarity	NPC209959
0.8258	Intermediate Similarity	NPC190043
0.8258	Intermediate Similarity	NPC23126
0.8258	Intermediate Similarity	NPC72158
0.8258	Intermediate Similarity	NPC169250
0.8258	Intermediate Similarity	NPC30501
0.8258	Intermediate Similarity	NPC98254
0.8258	Intermediate Similarity	NPC105157
0.8258	Intermediate Similarity	NPC162612
0.8258	Intermediate Similarity	NPC266689
0.8248	Intermediate Similarity	NPC191976
0.8248	Intermediate Similarity	NPC472308
0.8244	Intermediate Similarity	NPC87985
0.8244	Intermediate Similarity	NPC123506
0.8239	Intermediate Similarity	NPC208293
0.8235	Intermediate Similarity	NPC166480
0.8235	Intermediate Similarity	NPC282780
0.8235	Intermediate Similarity	NPC194970
0.8235	Intermediate Similarity	NPC213122
0.8222	Intermediate Similarity	NPC302844
0.8217	Intermediate Similarity	NPC253627
0.8217	Intermediate Similarity	NPC167323
0.8217	Intermediate Similarity	NPC120545
0.8217	Intermediate Similarity	NPC269923
0.8209	Intermediate Similarity	NPC259942
0.8207	Intermediate Similarity	NPC140133
0.8207	Intermediate Similarity	NPC37642
0.8203	Intermediate Similarity	NPC478121
0.8201	Intermediate Similarity	NPC26924
0.8201	Intermediate Similarity	NPC112789
0.8201	Intermediate Similarity	NPC242994
0.8201	Intermediate Similarity	NPC138099
0.8201	Intermediate Similarity	NPC19622
0.8197	Intermediate Similarity	NPC95172
0.8195	Intermediate Similarity	NPC221777
0.8195	Intermediate Similarity	NPC21305
0.8188	Intermediate Similarity	NPC277559
0.8188	Intermediate Similarity	NPC49911
0.8188	Intermediate Similarity	NPC62272
0.8182	Intermediate Similarity	NPC29883
0.8182	Intermediate Similarity	NPC71610
0.8182	Intermediate Similarity	NPC110211
0.8182	Intermediate Similarity	NPC25844
0.8182	Intermediate Similarity	NPC267846
0.8175	Intermediate Similarity	NPC173569
0.8175	Intermediate Similarity	NPC249272
0.8175	Intermediate Similarity	NPC477874
0.8175	Intermediate Similarity	NPC283088
0.8175	Intermediate Similarity	NPC475917
0.8175	Intermediate Similarity	NPC279463
0.8169	Intermediate Similarity	NPC260152
0.8168	Intermediate Similarity	NPC173978
0.8168	Intermediate Similarity	NPC265413
0.8168	Intermediate Similarity	NPC10154
0.8163	Intermediate Similarity	NPC62051
0.8162	Intermediate Similarity	NPC115458
0.8156	Intermediate Similarity	NPC193555
0.8156	Intermediate Similarity	NPC308572
0.8156	Intermediate Similarity	NPC248068
0.8154	Intermediate Similarity	NPC68167
0.8154	Intermediate Similarity	NPC244351
0.8154	Intermediate Similarity	NPC309765
0.8154	Intermediate Similarity	NPC11250
0.8154	Intermediate Similarity	NPC91478
0.8151	Intermediate Similarity	NPC11892
0.8151	Intermediate Similarity	NPC475093
0.8151	Intermediate Similarity	NPC48671
0.8148	Intermediate Similarity	NPC41847
0.8148	Intermediate Similarity	NPC72669
0.8148	Intermediate Similarity	NPC473777
0.8148	Intermediate Similarity	NPC474517
0.8143	Intermediate Similarity	NPC275903
0.8143	Intermediate Similarity	NPC476534
0.8143	Intermediate Similarity	NPC470035
0.8143	Intermediate Similarity	NPC168471
0.814	Intermediate Similarity	NPC159760
0.814	Intermediate Similarity	NPC179092
0.814	Intermediate Similarity	NPC178395
0.814	Intermediate Similarity	NPC35856
0.814	Intermediate Similarity	NPC190971
0.814	Intermediate Similarity	NPC244994
0.814	Intermediate Similarity	NPC222876
0.814	Intermediate Similarity	NPC272454
0.814	Intermediate Similarity	NPC301987
0.814	Intermediate Similarity	NPC115188
0.814	Intermediate Similarity	NPC292665
0.814	Intermediate Similarity	NPC26433
0.8138	Intermediate Similarity	NPC267469
0.8138	Intermediate Similarity	NPC87630
0.8138	Intermediate Similarity	NPC247219
0.8138	Intermediate Similarity	NPC35160

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 NPC229894 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	878
0.2-0.3	1219
0.3-0.4	2415
0.4-0.5	2487
0.5-0.6	1260
0.6-0.7	514
0.7-0.8	78
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8413	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7003	Approved
0.8188	Intermediate Similarity	NPD5408	Approved
0.8188	Intermediate Similarity	NPD5405	Approved
0.8188	Intermediate Similarity	NPD5406	Approved
0.8188	Intermediate Similarity	NPD5404	Approved
0.8182	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD5951	Approved
0.8106	Intermediate Similarity	NPD1164	Approved
0.8077	Intermediate Similarity	NPD1201	Approved
0.8074	Intermediate Similarity	NPD3764	Approved
0.8062	Intermediate Similarity	NPD3019	Approved
0.8014	Intermediate Similarity	NPD7458	Discontinued
0.8014	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD1470	Approved
0.7967	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD2932	Approved
0.7907	Intermediate Similarity	NPD9545	Approved
0.7883	Intermediate Similarity	NPD6663	Approved
0.7852	Intermediate Similarity	NPD5736	Approved
0.7786	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2799	Discontinued
0.7708	Intermediate Similarity	NPD4628	Phase 3
0.7708	Intermediate Similarity	NPD8166	Discontinued
0.7676	Intermediate Similarity	NPD2935	Discontinued
0.7671	Intermediate Similarity	NPD7390	Discontinued
0.7586	Intermediate Similarity	NPD3750	Approved
0.7566	Intermediate Similarity	NPD7819	Suspended
0.7561	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1929	Approved
0.7561	Intermediate Similarity	NPD1930	Approved
0.754	Intermediate Similarity	NPD74	Approved
0.754	Intermediate Similarity	NPD9266	Approved
0.7518	Intermediate Similarity	NPD2798	Approved
0.7481	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD9493	Approved
0.7481	Intermediate Similarity	NPD3972	Approved
0.7468	Intermediate Similarity	NPD7768	Phase 2
0.7466	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD3023	Approved
0.7463	Intermediate Similarity	NPD3026	Approved
0.746	Intermediate Similarity	NPD9263	Approved
0.746	Intermediate Similarity	NPD9267	Approved
0.746	Intermediate Similarity	NPD9264	Approved
0.7459	Intermediate Similarity	NPD3020	Approved
0.745	Intermediate Similarity	NPD6273	Approved
0.7448	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1240	Approved
0.7447	Intermediate Similarity	NPD943	Approved
0.7445	Intermediate Similarity	NPD2797	Approved
0.7444	Intermediate Similarity	NPD3024	Approved
0.7444	Intermediate Similarity	NPD3025	Approved
0.7434	Intermediate Similarity	NPD7411	Suspended
0.7421	Intermediate Similarity	NPD7473	Discontinued
0.7419	Intermediate Similarity	NPD7075	Discontinued
0.7417	Intermediate Similarity	NPD3226	Approved
0.7403	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1283	Approved
0.7361	Intermediate Similarity	NPD1510	Phase 2
0.7357	Intermediate Similarity	NPD7008	Discontinued
0.7357	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1809	Phase 2
0.7353	Intermediate Similarity	NPD1608	Approved
0.7343	Intermediate Similarity	NPD1607	Approved
0.7342	Intermediate Similarity	NPD6232	Discontinued
0.7338	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6099	Approved
0.731	Intermediate Similarity	NPD6100	Approved
0.7305	Intermediate Similarity	NPD3268	Approved
0.7305	Intermediate Similarity	NPD2313	Discontinued
0.7273	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2344	Approved
0.726	Intermediate Similarity	NPD2346	Discontinued
0.7259	Intermediate Similarity	NPD4626	Approved
0.7254	Intermediate Similarity	NPD8032	Phase 2
0.725	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3748	Approved
0.7239	Intermediate Similarity	NPD3091	Approved
0.7226	Intermediate Similarity	NPD9269	Phase 2
0.7222	Intermediate Similarity	NPD6651	Approved
0.7213	Intermediate Similarity	NPD2859	Approved
0.7213	Intermediate Similarity	NPD2860	Approved
0.7197	Intermediate Similarity	NPD3749	Approved
0.719	Intermediate Similarity	NPD845	Approved
0.719	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD9268	Approved
0.7183	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD2066	Phase 3
0.7176	Intermediate Similarity	NPD7635	Approved
0.7153	Intermediate Similarity	NPD1281	Approved
0.7153	Intermediate Similarity	NPD3092	Approved
0.7152	Intermediate Similarity	NPD2534	Approved
0.7152	Intermediate Similarity	NPD2532	Approved
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2533	Approved
0.7143	Intermediate Similarity	NPD9261	Approved
0.7143	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD6599	Discontinued
0.7143	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7236	Approved
0.7133	Intermediate Similarity	NPD3300	Phase 2
0.7132	Intermediate Similarity	NPD17	Approved
0.7132	Intermediate Similarity	NPD4059	Approved
0.7131	Intermediate Similarity	NPD2933	Approved
0.7131	Intermediate Similarity	NPD2934	Approved
0.7123	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4308	Phase 3
0.7122	Intermediate Similarity	NPD1876	Approved
0.7117	Intermediate Similarity	NPD5844	Phase 1
0.7095	Intermediate Similarity	NPD1549	Phase 2
0.7086	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4476	Approved
0.7075	Intermediate Similarity	NPD4477	Approved
0.7075	Intermediate Similarity	NPD2796	Approved
0.7071	Intermediate Similarity	NPD1203	Approved
0.7068	Intermediate Similarity	NPD2629	Approved
0.7068	Intermediate Similarity	NPD9281	Approved
0.7067	Intermediate Similarity	NPD2309	Approved
0.7063	Intermediate Similarity	NPD846	Approved
0.7063	Intermediate Similarity	NPD940	Approved
0.7054	Intermediate Similarity	NPD2342	Discontinued
0.7051	Intermediate Similarity	NPD6801	Discontinued
0.705	Intermediate Similarity	NPD1755	Approved
0.7047	Intermediate Similarity	NPD2800	Approved
0.7037	Intermediate Similarity	NPD7610	Discontinued
0.7034	Intermediate Similarity	NPD6355	Discontinued
0.7034	Intermediate Similarity	NPD230	Phase 1
0.7027	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD256	Approved
0.7015	Intermediate Similarity	NPD255	Approved
0.7007	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3400	Discontinued
0.6993	Remote Similarity	NPD7095	Approved
0.6984	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD9717	Approved
0.6978	Remote Similarity	NPD4878	Approved
0.6974	Remote Similarity	NPD6799	Approved
0.6972	Remote Similarity	NPD4208	Discontinued
0.697	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4060	Phase 1
0.6957	Remote Similarity	NPD8127	Discontinued
0.6954	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6190	Approved
0.6953	Remote Similarity	NPD5909	Discontinued
0.6951	Remote Similarity	NPD7177	Discontinued
0.695	Remote Similarity	NPD3094	Phase 2
0.695	Remote Similarity	NPD3266	Approved
0.695	Remote Similarity	NPD3267	Approved
0.6947	Remote Similarity	NPD3022	Approved
0.6947	Remote Similarity	NPD3021	Approved
0.6947	Remote Similarity	NPD4750	Phase 3
0.6944	Remote Similarity	NPD6798	Discontinued
0.6942	Remote Similarity	NPD9256	Approved
0.6942	Remote Similarity	NPD9258	Approved
0.6934	Remote Similarity	NPD5691	Approved
0.6933	Remote Similarity	NPD1243	Approved
0.6923	Remote Similarity	NPD6832	Phase 2
0.6909	Remote Similarity	NPD6020	Phase 2
0.6903	Remote Similarity	NPD7239	Suspended
0.6887	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3095	Discontinued
0.6884	Remote Similarity	NPD4589	Approved
0.6882	Remote Similarity	NPD8150	Discontinued
0.688	Remote Similarity	NPD288	Approved
0.6866	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6959	Discontinued
0.6849	Remote Similarity	NPD4140	Approved
0.6849	Remote Similarity	NPD4307	Phase 2
0.6849	Remote Similarity	NPD2979	Phase 3
0.6846	Remote Similarity	NPD1551	Phase 2
0.6839	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7427	Discontinued
0.6829	Remote Similarity	NPD1088	Approved
0.6828	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1237	Approved
0.6812	Remote Similarity	NPD4093	Discontinued
0.6812	Remote Similarity	NPD1651	Approved
0.681	Remote Similarity	NPD7229	Phase 3
0.6809	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4207	Discontinued
0.6802	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.68	Remote Similarity	NPD844	Approved
0.6797	Remote Similarity	NPD7440	Discontinued
0.6797	Remote Similarity	NPD1932	Approved
0.6792	Remote Similarity	NPD1465	Phase 2
0.6786	Remote Similarity	NPD422	Phase 1
0.6779	Remote Similarity	NPD7033	Discontinued
0.6774	Remote Similarity	NPD5049	Phase 3
0.6774	Remote Similarity	NPD5122	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