NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	428.29
Volume:	465.937
LogP:	5.089
LogD:	4.315
LogS:	-3.69
# Rotatable Bonds:	4
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.558
Synthetic Accessibility Score:	4.432
Fsp3:	0.741
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.19
MDCK Permeability:	1.83E-05
Pgp-inhibitor:	0.203
Pgp-substrate:	0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.74

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.139
Plasma Protein Binding (PPB):	98.86%
Volume Distribution (VD):	0.427
Pgp-substrate:	2.83%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.506
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.431
CYP2C9-inhibitor:	0.142
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.13
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.1
CYP3A4-substrate:	0.143

ADMET: Excretion

Clearance (CL):	3.395
Half-life (T1/2):	0.672

ADMET: Toxicity

hERG Blockers:	0.165
Human Hepatotoxicity (H-HT):	0.397
Drug-inuced Liver Injury (DILI):	0.344
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.658
Carcinogencity:	0.023
Eye Corrosion:	0.009
Eye Irritation:	0.496
Respiratory Toxicity:	0.927

Download Data

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

Natural Product: NPC477592

Natural Product ID:	NPC477592
*Common Name:**	Comnastin A
IUPAC Name:	3-[[(3R,3aR,5aS,6R,7R,9aS,9bR)-3-(hydroxymethyl)-3,3a,6,7,9a-pentamethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-cyclopenta[a]naphthalen-6-yl]methyl]-4-hydroxybenzoic acid
Synonyms:
Standard InCHIKey:	GADPAHOVYVZUKK-VQMVVOJVSA-N
Standard InCHI:	InChI=1S/C27H40O4/c1-17-8-12-25(3)21(10-13-27(5)22(25)9-11-24(27,2)16-28)26(17,4)15-19-14-18(23(30)31)6-7-20(19)29/h6-7,14,17,21-22,28-29H,8-13,15-16H2,1-5H3,(H,30,31)/t17-,21-,22-,24+,25+,26-,27-/m1/s1
SMILES:	C[C@@H]1CC[C@@]2([C@H]3CC[C@@]([C@@]3(CC[C@H]2[C@]1(C)CC4=C(C=CC(=C4)C(=O)O)O)C)(C)CO)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44583751
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO15743	0stoc commune	Species	0stocaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10096870]
NPO15743	0stoc commune	Species	0stocaceae	Bacteria	n.a.	Mellingen, Switzerland	1965	PMID[10757714]
NPO15743	0stoc commune	Species	0stocaceae	Bacteria	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
MIC	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	32	ppm	PMID[10757714]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	16	ppm	PMID[10757714]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	128	ppm	PMID[10757714]

☑ 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 NPC477592 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	285
0.1-0.2	1198
0.2-0.3	2246
0.3-0.4	4738
0.4-0.5	10383
0.5-0.6	10368
0.6-0.7	10642
0.7-0.8	2725
0.8-0.85	94
0.85-0.9	10
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC477593
0.9769	High Similarity	NPC477594
0.9695	High Similarity	NPC477596
0.9556	High Similarity	NPC477595
0.9308	High Similarity	NPC229894
0.9242	High Similarity	NPC18798
0.9237	High Similarity	NPC117899
0.916	High Similarity	NPC193203
0.8951	High Similarity	NPC279442
0.8794	High Similarity	NPC477209
0.8779	High Similarity	NPC174991
0.8676	High Similarity	NPC471851
0.863	High Similarity	NPC142654
0.8623	High Similarity	NPC202225
0.8601	High Similarity	NPC477207
0.8561	High Similarity	NPC475192
0.8551	High Similarity	NPC78307
0.8519	High Similarity	NPC69424
0.8519	High Similarity	NPC84672
0.8519	High Similarity	NPC176130
0.8519	High Similarity	NPC78364
0.8511	High Similarity	NPC234548
0.8511	High Similarity	NPC248287
0.8507	High Similarity	NPC137416
0.8493	Intermediate Similarity	NPC325032
0.8493	Intermediate Similarity	NPC5568
0.8493	Intermediate Similarity	NPC477483
0.8483	Intermediate Similarity	NPC75295
0.8462	Intermediate Similarity	NPC273282
0.8462	Intermediate Similarity	NPC474890
0.8462	Intermediate Similarity	NPC161943
0.8456	Intermediate Similarity	NPC3009
0.8444	Intermediate Similarity	NPC471935
0.8444	Intermediate Similarity	NPC471930
0.8444	Intermediate Similarity	NPC471929
0.844	Intermediate Similarity	NPC475957
0.8425	Intermediate Similarity	NPC477208
0.8417	Intermediate Similarity	NPC475627
0.8417	Intermediate Similarity	NPC18982
0.8417	Intermediate Similarity	NPC475346
0.8417	Intermediate Similarity	NPC477139
0.8417	Intermediate Similarity	NPC475457
0.8417	Intermediate Similarity	NPC49742
0.8406	Intermediate Similarity	NPC476847
0.8394	Intermediate Similarity	NPC276238
0.8392	Intermediate Similarity	NPC172311
0.8392	Intermediate Similarity	NPC471853
0.8382	Intermediate Similarity	NPC72667
0.8378	Intermediate Similarity	NPC116292
0.8378	Intermediate Similarity	NPC267469
0.8378	Intermediate Similarity	NPC179128
0.8378	Intermediate Similarity	NPC87630
0.8356	Intermediate Similarity	NPC258856
0.8356	Intermediate Similarity	NPC208293
0.8345	Intermediate Similarity	NPC100242
0.8333	Intermediate Similarity	NPC108129
0.8333	Intermediate Similarity	NPC2681
0.8333	Intermediate Similarity	NPC272907
0.8322	Intermediate Similarity	NPC140133
0.8321	Intermediate Similarity	NPC473744
0.8311	Intermediate Similarity	NPC477206
0.8309	Intermediate Similarity	NPC254492
0.8308	Intermediate Similarity	NPC83718
0.8278	Intermediate Similarity	NPC62051
0.8276	Intermediate Similarity	NPC248068
0.8267	Intermediate Similarity	NPC48671
0.8261	Intermediate Similarity	NPC303910
0.8261	Intermediate Similarity	NPC171460
0.8255	Intermediate Similarity	NPC247219
0.8255	Intermediate Similarity	NPC35160
0.8255	Intermediate Similarity	NPC327962
0.8255	Intermediate Similarity	NPC162569
0.8243	Intermediate Similarity	NPC66991
0.8239	Intermediate Similarity	NPC249817
0.8235	Intermediate Similarity	NPC137750
0.8235	Intermediate Similarity	NPC87985
0.8227	Intermediate Similarity	NPC11266
0.8227	Intermediate Similarity	NPC194970
0.8219	Intermediate Similarity	NPC271451
0.8209	Intermediate Similarity	NPC249340
0.8209	Intermediate Similarity	NPC162935
0.8207	Intermediate Similarity	NPC477275
0.8207	Intermediate Similarity	NPC91019
0.8207	Intermediate Similarity	NPC106519
0.8205	Intermediate Similarity	NPC161151
0.8201	Intermediate Similarity	NPC72915
0.8188	Intermediate Similarity	NPC17600
0.8188	Intermediate Similarity	NPC96024
0.8182	Intermediate Similarity	NPC22676
0.8182	Intermediate Similarity	NPC216940
0.8182	Intermediate Similarity	NPC475482
0.8182	Intermediate Similarity	NPC198621
0.8182	Intermediate Similarity	NPC170718
0.8176	Intermediate Similarity	NPC286038
0.8175	Intermediate Similarity	NPC110211
0.8175	Intermediate Similarity	NPC269598
0.8175	Intermediate Similarity	NPC71610
0.8175	Intermediate Similarity	NPC473751
0.8175	Intermediate Similarity	NPC204579
0.8169	Intermediate Similarity	NPC475917
0.8169	Intermediate Similarity	NPC173569
0.8169	Intermediate Similarity	NPC279463
0.8169	Intermediate Similarity	NPC477874
0.8162	Intermediate Similarity	NPC12818
0.8162	Intermediate Similarity	NPC184219
0.8162	Intermediate Similarity	NPC199273
0.8162	Intermediate Similarity	NPC265413
0.8162	Intermediate Similarity	NPC10154
0.8156	Intermediate Similarity	NPC126516
0.8156	Intermediate Similarity	NPC48929
0.8151	Intermediate Similarity	NPC184935
0.8148	Intermediate Similarity	NPC121168
0.8148	Intermediate Similarity	NPC67300
0.8146	Intermediate Similarity	NPC124842
0.8146	Intermediate Similarity	NPC11892
0.8143	Intermediate Similarity	NPC93015
0.8143	Intermediate Similarity	NPC473777
0.8138	Intermediate Similarity	NPC476534
0.8138	Intermediate Similarity	NPC315578
0.8138	Intermediate Similarity	NPC469911
0.8138	Intermediate Similarity	NPC3218
0.8134	Intermediate Similarity	NPC216216
0.8134	Intermediate Similarity	NPC164852
0.8134	Intermediate Similarity	NPC241001
0.8133	Intermediate Similarity	NPC52931
0.8129	Intermediate Similarity	NPC194979
0.8125	Intermediate Similarity	NPC20210
0.812	Intermediate Similarity	NPC473767
0.812	Intermediate Similarity	NPC42657
0.8116	Intermediate Similarity	NPC262936
0.8116	Intermediate Similarity	NPC30491
0.8112	Intermediate Similarity	NPC118919
0.8108	Intermediate Similarity	NPC478160
0.8108	Intermediate Similarity	NPC8102
0.8108	Intermediate Similarity	NPC66894
0.8106	Intermediate Similarity	NPC174087
0.8105	Intermediate Similarity	NPC472807
0.8101	Intermediate Similarity	NPC200726
0.8099	Intermediate Similarity	NPC293454
0.8099	Intermediate Similarity	NPC204582
0.8099	Intermediate Similarity	NPC475088
0.8092	Intermediate Similarity	NPC257847
0.8088	Intermediate Similarity	NPC275145
0.8088	Intermediate Similarity	NPC471187
0.8088	Intermediate Similarity	NPC198014
0.8085	Intermediate Similarity	NPC302844
0.8085	Intermediate Similarity	NPC175738
0.8079	Intermediate Similarity	NPC37642
0.8074	Intermediate Similarity	NPC369
0.8074	Intermediate Similarity	NPC293831
0.8074	Intermediate Similarity	NPC253627
0.8074	Intermediate Similarity	NPC295034
0.8069	Intermediate Similarity	NPC19622
0.8069	Intermediate Similarity	NPC26924
0.8069	Intermediate Similarity	NPC112789
0.8067	Intermediate Similarity	NPC473719
0.806	Intermediate Similarity	NPC133389
0.806	Intermediate Similarity	NPC234337
0.806	Intermediate Similarity	NPC183339
0.806	Intermediate Similarity	NPC190501
0.806	Intermediate Similarity	NPC318552
0.8056	Intermediate Similarity	NPC53001
0.8056	Intermediate Similarity	NPC36868
0.805	Intermediate Similarity	NPC177362
0.8042	Intermediate Similarity	NPC290803
0.8041	Intermediate Similarity	NPC260152
0.8041	Intermediate Similarity	NPC126707
0.8039	Intermediate Similarity	NPC470102
0.8029	Intermediate Similarity	NPC474532
0.8029	Intermediate Similarity	NPC181334
0.8028	Intermediate Similarity	NPC329913
0.8028	Intermediate Similarity	NPC37299
0.8028	Intermediate Similarity	NPC111845
0.8028	Intermediate Similarity	NPC180261
0.8028	Intermediate Similarity	NPC203486
0.8028	Intermediate Similarity	NPC139074
0.8028	Intermediate Similarity	NPC213485
0.8028	Intermediate Similarity	NPC52407
0.8028	Intermediate Similarity	NPC40524
0.8027	Intermediate Similarity	NPC135524
0.8027	Intermediate Similarity	NPC474961
0.8027	Intermediate Similarity	NPC308572
0.8026	Intermediate Similarity	NPC477276
0.8026	Intermediate Similarity	NPC475093
0.8015	Intermediate Similarity	NPC282577
0.8015	Intermediate Similarity	NPC11250
0.8014	Intermediate Similarity	NPC168471
0.8014	Intermediate Similarity	NPC125153
0.8014	Intermediate Similarity	NPC41847
0.8014	Intermediate Similarity	NPC275903
0.8014	Intermediate Similarity	NPC27518
0.8014	Intermediate Similarity	NPC475042
0.8014	Intermediate Similarity	NPC470035
0.8014	Intermediate Similarity	NPC169452
0.8014	Intermediate Similarity	NPC304110
0.8014	Intermediate Similarity	NPC472801
0.8014	Intermediate Similarity	NPC181560
0.8	Intermediate Similarity	NPC4214
0.8	Intermediate Similarity	NPC162751
0.8	Intermediate Similarity	NPC52161

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 NPC477592 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	767
0.2-0.3	1304
0.3-0.4	2467
0.4-0.5	2419
0.5-0.6	1407
0.6-0.7	475
0.7-0.8	63
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8143	Intermediate Similarity	NPD6663	Approved
0.8116	Intermediate Similarity	NPD5736	Approved
0.806	Intermediate Similarity	NPD3019	Approved
0.8013	Intermediate Similarity	NPD7458	Discontinued
0.7959	Intermediate Similarity	NPD7003	Approved
0.7931	Intermediate Similarity	NPD5404	Approved
0.7931	Intermediate Similarity	NPD5406	Approved
0.7931	Intermediate Similarity	NPD5405	Approved
0.7931	Intermediate Similarity	NPD5408	Approved
0.7926	Intermediate Similarity	NPD2932	Approved
0.7891	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD4628	Phase 3
0.7817	Intermediate Similarity	NPD3764	Approved
0.7815	Intermediate Similarity	NPD6273	Approved
0.7744	Intermediate Similarity	NPD5951	Approved
0.774	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7236	Approved
0.7718	Intermediate Similarity	NPD8166	Discontinued
0.7714	Intermediate Similarity	NPD1470	Approved
0.7681	Intermediate Similarity	NPD1201	Approved
0.7647	Intermediate Similarity	NPD9545	Approved
0.7647	Intermediate Similarity	NPD3091	Approved
0.7643	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD3023	Approved
0.7609	Intermediate Similarity	NPD3026	Approved
0.7591	Intermediate Similarity	NPD3024	Approved
0.7591	Intermediate Similarity	NPD3025	Approved
0.7589	Intermediate Similarity	NPD1164	Approved
0.7557	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD3092	Approved
0.7535	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD8127	Discontinued
0.75	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7239	Suspended
0.7468	Intermediate Similarity	NPD7819	Suspended
0.7465	Intermediate Similarity	NPD3094	Phase 2
0.7451	Intermediate Similarity	NPD7390	Discontinued
0.745	Intermediate Similarity	NPD2935	Discontinued
0.741	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3095	Discontinued
0.7403	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2799	Discontinued
0.7375	Intermediate Similarity	NPD7768	Phase 2
0.7342	Intermediate Similarity	NPD7411	Suspended
0.7333	Intermediate Similarity	NPD7473	Discontinued
0.7329	Intermediate Similarity	NPD7075	Discontinued
0.7325	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2534	Approved
0.729	Intermediate Similarity	NPD2532	Approved
0.729	Intermediate Similarity	NPD2533	Approved
0.7286	Intermediate Similarity	NPD4059	Approved
0.7279	Intermediate Similarity	NPD8032	Phase 2
0.7273	Intermediate Similarity	NPD1876	Approved
0.7267	Intermediate Similarity	NPD1510	Phase 2
0.726	Intermediate Similarity	NPD7008	Discontinued
0.7256	Intermediate Similarity	NPD6232	Discontinued
0.7255	Intermediate Similarity	NPD3750	Approved
0.7255	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3972	Approved
0.725	Intermediate Similarity	NPD5761	Phase 2
0.725	Intermediate Similarity	NPD5760	Phase 2
0.725	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5844	Phase 1
0.7237	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4140	Approved
0.7215	Intermediate Similarity	NPD3226	Approved
0.7194	Intermediate Similarity	NPD7610	Discontinued
0.7181	Intermediate Similarity	NPD6355	Discontinued
0.7179	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4380	Phase 2
0.717	Intermediate Similarity	NPD6599	Discontinued
0.7169	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7961	Discontinued
0.7153	Intermediate Similarity	NPD1283	Approved
0.7133	Intermediate Similarity	NPD1607	Approved
0.7122	Intermediate Similarity	NPD9493	Approved
0.7114	Intermediate Similarity	NPD943	Approved
0.7114	Intermediate Similarity	NPD1240	Approved
0.7095	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6801	Discontinued
0.707	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2346	Discontinued
0.7059	Intermediate Similarity	NPD5762	Approved
0.7059	Intermediate Similarity	NPD6002	Phase 3
0.7059	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6005	Phase 3
0.7059	Intermediate Similarity	NPD5763	Approved
0.7059	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6004	Phase 3
0.7055	Intermediate Similarity	NPD7057	Phase 3
0.7055	Intermediate Similarity	NPD7058	Phase 2
0.7055	Intermediate Similarity	NPD2798	Approved
0.7045	Intermediate Similarity	NPD1930	Approved
0.7045	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1929	Approved
0.7042	Intermediate Similarity	NPD4626	Approved
0.7042	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7033	Discontinued
0.7037	Intermediate Similarity	NPD74	Approved
0.7037	Intermediate Similarity	NPD9266	Approved
0.7032	Intermediate Similarity	NPD3400	Discontinued
0.7021	Intermediate Similarity	NPD7741	Discontinued
0.702	Intermediate Similarity	NPD6651	Approved
0.7013	Intermediate Similarity	NPD1549	Phase 2
0.7012	Intermediate Similarity	NPD3749	Approved
0.7011	Intermediate Similarity	NPD8150	Discontinued
0.7006	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6100	Approved
0.6993	Remote Similarity	NPD6099	Approved
0.6988	Remote Similarity	NPD7199	Phase 2
0.6987	Remote Similarity	NPD6190	Approved
0.6986	Remote Similarity	NPD2797	Approved
0.6982	Remote Similarity	NPD7177	Discontinued
0.6982	Remote Similarity	NPD7799	Discontinued
0.698	Remote Similarity	NPD3268	Approved
0.698	Remote Similarity	NPD2313	Discontinued
0.6978	Remote Similarity	NPD2629	Approved
0.6963	Remote Similarity	NPD9264	Approved
0.6963	Remote Similarity	NPD9267	Approved
0.6963	Remote Similarity	NPD9263	Approved
0.6957	Remote Similarity	NPD6858	Approved
0.6957	Remote Similarity	NPD7094	Approved
0.6954	Remote Similarity	NPD230	Phase 1
0.6954	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2344	Approved
0.6948	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD3020	Approved
0.6944	Remote Similarity	NPD1281	Approved
0.6943	Remote Similarity	NPD3300	Phase 2
0.6933	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4308	Phase 3
0.6928	Remote Similarity	NPD7305	Phase 1
0.6928	Remote Similarity	NPD3748	Approved
0.6923	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7685	Pre-registration
0.6919	Remote Similarity	NPD6765	Approved
0.6919	Remote Similarity	NPD6764	Approved
0.6914	Remote Similarity	NPD8434	Phase 2
0.6899	Remote Similarity	NPD6799	Approved
0.6897	Remote Similarity	NPD9269	Phase 2
0.6897	Remote Similarity	NPD1608	Approved
0.6887	Remote Similarity	NPD2979	Phase 3
0.6887	Remote Similarity	NPD4060	Phase 1
0.6886	Remote Similarity	NPD6959	Discontinued
0.6884	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1551	Phase 2
0.6883	Remote Similarity	NPD4476	Approved
0.6883	Remote Similarity	NPD2796	Approved
0.6883	Remote Similarity	NPD4477	Approved
0.6875	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD37	Approved
0.6867	Remote Similarity	NPD6798	Discontinued
0.6859	Remote Similarity	NPD2800	Approved
0.6854	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD9268	Approved
0.6853	Remote Similarity	NPD5691	Approved
0.6852	Remote Similarity	NPD7028	Phase 2
0.6846	Remote Similarity	NPD6832	Phase 2
0.6846	Remote Similarity	NPD1809	Phase 2
0.6845	Remote Similarity	NPD7229	Phase 3
0.6842	Remote Similarity	NPD5735	Approved
0.6839	Remote Similarity	NPD8313	Approved
0.6839	Remote Similarity	NPD8312	Approved
0.6836	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7635	Approved
0.6824	Remote Similarity	NPD4624	Approved
0.6818	Remote Similarity	NPD7743	Approved
0.6818	Remote Similarity	NPD2066	Phase 3
0.6818	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7742	Approved
0.6815	Remote Similarity	NPD4110	Phase 3
0.6815	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7009	Phase 2
0.6779	Remote Similarity	NPD4208	Discontinued
0.6776	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD3620	Phase 2
0.6772	Remote Similarity	NPD2309	Approved
0.677	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6784	Approved
0.6761	Remote Similarity	NPD6785	Approved
0.6757	Remote Similarity	NPD7497	Discontinued
0.6757	Remote Similarity	NPD1203	Approved
0.6755	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4967	Phase 2
0.6747	Remote Similarity	NPD4966	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