NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	398.17
Volume:	412.344
LogP:	5.756
LogD:	4.151
LogS:	-3.985
# Rotatable Bonds:	6
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.547
Synthetic Accessibility Score:	3.617
Fsp3:	0.348
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.785
MDCK Permeability:	1.572222936374601e-05
Pgp-inhibitor:	0.775
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.042
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	88.40335845947266%
Volume Distribution (VD):	0.719
Pgp-substrate:	13.537023544311523%

ADMET: Metabolism

CYP1A2-inhibitor:	0.845
CYP1A2-substrate:	0.697
CYP2C19-inhibitor:	0.802
CYP2C19-substrate:	0.533
CYP2C9-inhibitor:	0.741
CYP2C9-substrate:	0.881
CYP2D6-inhibitor:	0.856
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.654
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	12.384
Half-life (T1/2):	0.316

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.808
Drug-inuced Liver Injury (DILI):	0.465
AMES Toxicity:	0.405
Rat Oral Acute Toxicity:	0.219
Maximum Recommended Daily Dose:	0.613
Skin Sensitization:	0.63
Carcinogencity:	0.538
Eye Corrosion:	0.003
Eye Irritation:	0.11
Respiratory Toxicity:	0.601

Download Data

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

Natural Product: NPC477689

Natural Product ID:	NPC477689
*Common Name:**	3-Methyl-3-(4-methyl-3-pentenyl)-5,10-dihydroxy-7-methoxy-3H-naphtho[2,1-b]pyran-9-carboxylic acid methyl ester
IUPAC Name:	methyl 5,10-dihydroxy-7-methoxy-3-methyl-3-(4-methylpent-3-enyl)benzo[f]chromene-9-carboxylate
Synonyms:
Standard InCHIKey:	KOZKSXRTQNRWGJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H26O6/c1-13(2)7-6-9-23(3)10-8-14-19-15(11-17(24)21(14)29-23)18(27-4)12-16(20(19)25)22(26)28-5/h7-8,10-12,24-25H,6,9H2,1-5H3
SMILES:	CC(=CCCC1(C=CC2=C3C(=CC(=C2O1)O)C(=CC(=C3O)C(=O)OC)OC)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11112105
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO33631	Pentas bussei	Species	Rubiaceae	Eukaryota	Roots	Mombasa, coastal region of Kenya	2010-JUL	PMID[22709138]

☑ 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
LD50	1

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	LD50	=	86.39	nM	PMID[22709138]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	30560	nM	PMID[22709138]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	85040	nM	PMID[22709138]

☑ 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 NPC477689 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	396
0.1-0.2	1643
0.2-0.3	3804
0.3-0.4	9129
0.4-0.5	9043
0.5-0.6	3350
0.6-0.7	5369
0.7-0.8	7336
0.8-0.85	2049
0.85-0.9	554
0.9-0.95	23
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9481	High Similarity	NPC477691
0.9416	High Similarity	NPC477690
0.9321	High Similarity	NPC124470
0.9321	High Similarity	NPC109827
0.925	High Similarity	NPC270837
0.9187	High Similarity	NPC144843
0.9187	High Similarity	NPC294965
0.9146	High Similarity	NPC158226
0.9141	High Similarity	NPC165979
0.9141	High Similarity	NPC163130
0.9136	High Similarity	NPC37870
0.9125	High Similarity	NPC66288
0.9119	High Similarity	NPC45846
0.9119	High Similarity	NPC477692
0.908	High Similarity	NPC234331
0.9074	High Similarity	NPC472450
0.9074	High Similarity	NPC239752
0.9074	High Similarity	NPC275780
0.9062	High Similarity	NPC47623
0.9062	High Similarity	NPC476980
0.9057	High Similarity	NPC143328
0.9032	High Similarity	NPC55327
0.9026	High Similarity	NPC60389
0.9024	High Similarity	NPC99613
0.9024	High Similarity	NPC49487
0.9018	High Similarity	NPC39091
0.9018	High Similarity	NPC29160
0.9012	High Similarity	NPC189473
0.9012	High Similarity	NPC23298
0.9012	High Similarity	NPC236132
0.9012	High Similarity	NPC207690
0.9012	High Similarity	NPC234004
0.9006	High Similarity	NPC61010
0.9	High Similarity	NPC474290
0.8957	High Similarity	NPC26386
0.8957	High Similarity	NPC303174
0.8951	High Similarity	NPC83922
0.8951	High Similarity	NPC472448
0.8951	High Similarity	NPC229632
0.8951	High Similarity	NPC8300
0.8951	High Similarity	NPC329760
0.8944	High Similarity	NPC130955
0.8944	High Similarity	NPC56085
0.8944	High Similarity	NPC14353
0.8944	High Similarity	NPC228785
0.8938	High Similarity	NPC476981
0.8924	High Similarity	NPC199773
0.8922	High Similarity	NPC227906
0.8909	High Similarity	NPC476637
0.8903	High Similarity	NPC211565
0.8902	High Similarity	NPC472449
0.8902	High Similarity	NPC43319
0.8896	High Similarity	NPC474350
0.8896	High Similarity	NPC220313
0.8896	High Similarity	NPC236521
0.8896	High Similarity	NPC156082
0.8896	High Similarity	NPC152659
0.8896	High Similarity	NPC197168
0.8896	High Similarity	NPC248638
0.8889	High Similarity	NPC278052
0.8889	High Similarity	NPC259456
0.8889	High Similarity	NPC167678
0.8889	High Similarity	NPC311740
0.8889	High Similarity	NPC29876
0.8889	High Similarity	NPC258331
0.8889	High Similarity	NPC40491
0.8882	High Similarity	NPC100123
0.8882	High Similarity	NPC476242
0.8876	High Similarity	NPC113446
0.8875	High Similarity	NPC472455
0.8875	High Similarity	NPC472453
0.8862	High Similarity	NPC181523
0.8848	High Similarity	NPC218226
0.8841	High Similarity	NPC112981
0.8841	High Similarity	NPC25361
0.8841	High Similarity	NPC85057
0.8841	High Similarity	NPC130920
0.8834	High Similarity	NPC470694
0.8834	High Similarity	NPC25152
0.8834	High Similarity	NPC261470
0.8827	High Similarity	NPC139036
0.8827	High Similarity	NPC119224
0.8827	High Similarity	NPC471973
0.8827	High Similarity	NPC204290
0.8827	High Similarity	NPC84571
0.8827	High Similarity	NPC320359
0.882	High Similarity	NPC296044
0.882	High Similarity	NPC262286
0.882	High Similarity	NPC36852
0.882	High Similarity	NPC241904
0.882	High Similarity	NPC165977
0.882	High Similarity	NPC300727
0.882	High Similarity	NPC78225
0.882	High Similarity	NPC167098
0.882	High Similarity	NPC217677
0.882	High Similarity	NPC136674
0.8812	High Similarity	NPC234255
0.8812	High Similarity	NPC256612
0.8812	High Similarity	NPC286052
0.8812	High Similarity	NPC20830
0.8812	High Similarity	NPC472280
0.881	High Similarity	NPC289147
0.881	High Similarity	NPC139350
0.8805	High Similarity	NPC137125
0.8805	High Similarity	NPC295646
0.8805	High Similarity	NPC3744
0.8805	High Similarity	NPC75069
0.8805	High Similarity	NPC175978
0.8802	High Similarity	NPC260263
0.8802	High Similarity	NPC247964
0.8797	High Similarity	NPC31132
0.8795	High Similarity	NPC476279
0.8788	High Similarity	NPC20216
0.8788	High Similarity	NPC170245
0.8788	High Similarity	NPC472452
0.878	High Similarity	NPC303460
0.878	High Similarity	NPC306321
0.878	High Similarity	NPC186686
0.878	High Similarity	NPC7483
0.8773	High Similarity	NPC32694
0.8773	High Similarity	NPC474187
0.8765	High Similarity	NPC83763
0.8765	High Similarity	NPC315157
0.8765	High Similarity	NPC204879
0.8765	High Similarity	NPC238381
0.8765	High Similarity	NPC168616
0.8758	High Similarity	NPC274730
0.8758	High Similarity	NPC68093
0.8758	High Similarity	NPC142339
0.8758	High Similarity	NPC138243
0.8758	High Similarity	NPC279605
0.8758	High Similarity	NPC191146
0.8758	High Similarity	NPC54928
0.875	High Similarity	NPC310794
0.875	High Similarity	NPC274327
0.875	High Similarity	NPC145379
0.875	High Similarity	NPC69394
0.875	High Similarity	NPC176775
0.875	High Similarity	NPC47781
0.875	High Similarity	NPC183878
0.875	High Similarity	NPC231018
0.875	High Similarity	NPC22519
0.875	High Similarity	NPC298802
0.875	High Similarity	NPC255350
0.875	High Similarity	NPC160951
0.8743	High Similarity	NPC239440
0.8743	High Similarity	NPC10576
0.8743	High Similarity	NPC101107
0.8743	High Similarity	NPC20543
0.8743	High Similarity	NPC246716
0.8743	High Similarity	NPC17219
0.8742	High Similarity	NPC70320
0.8742	High Similarity	NPC302783
0.8742	High Similarity	NPC473201
0.8735	High Similarity	NPC6588
0.8735	High Similarity	NPC477154
0.8735	High Similarity	NPC126204
0.8735	High Similarity	NPC117854
0.8735	High Similarity	NPC292788
0.8735	High Similarity	NPC272485
0.8734	High Similarity	NPC285527
0.8734	High Similarity	NPC106334
0.8727	High Similarity	NPC50960
0.8727	High Similarity	NPC156432
0.8727	High Similarity	NPC326520
0.872	High Similarity	NPC108767
0.872	High Similarity	NPC474150
0.872	High Similarity	NPC474162
0.872	High Similarity	NPC81679
0.8712	High Similarity	NPC474960
0.8712	High Similarity	NPC80375
0.8712	High Similarity	NPC45146
0.8712	High Similarity	NPC475886
0.8712	High Similarity	NPC246478
0.8712	High Similarity	NPC235018
0.8712	High Similarity	NPC200746
0.8712	High Similarity	NPC36217
0.8712	High Similarity	NPC474287
0.8706	High Similarity	NPC207467
0.8704	High Similarity	NPC178976
0.8704	High Similarity	NPC236796
0.8704	High Similarity	NPC44199
0.8704	High Similarity	NPC302258
0.8704	High Similarity	NPC37543
0.8704	High Similarity	NPC218313
0.8704	High Similarity	NPC472963
0.8704	High Similarity	NPC474681
0.8704	High Similarity	NPC199463
0.8696	High Similarity	NPC208197
0.8696	High Similarity	NPC167815
0.8696	High Similarity	NPC256925
0.8696	High Similarity	NPC4455
0.8696	High Similarity	NPC152951
0.8696	High Similarity	NPC146165
0.8696	High Similarity	NPC92659
0.8696	High Similarity	NPC57674
0.8696	High Similarity	NPC227325
0.8696	High Similarity	NPC230149
0.8696	High Similarity	NPC196439
0.8696	High Similarity	NPC213622

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 NPC477689 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	971
0.2-0.3	1674
0.3-0.4	2589
0.4-0.5	1821
0.5-0.6	1012
0.6-0.7	509
0.7-0.8	186
0.8-0.85	27
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8834	High Similarity	NPD6232	Discontinued
0.875	High Similarity	NPD2801	Approved
0.8683	High Similarity	NPD5844	Phase 1
0.8675	High Similarity	NPD7473	Discontinued
0.8506	High Similarity	NPD8397	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD2935	Discontinued
0.8405	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1934	Approved
0.8293	Intermediate Similarity	NPD1465	Phase 2
0.8272	Intermediate Similarity	NPD3226	Approved
0.8269	Intermediate Similarity	NPD2346	Discontinued
0.8242	Intermediate Similarity	NPD3817	Phase 2
0.8193	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD3882	Suspended
0.8187	Intermediate Similarity	NPD1511	Approved
0.8187	Intermediate Similarity	NPD3818	Discontinued
0.8182	Intermediate Similarity	NPD7819	Suspended
0.8161	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD5494	Approved
0.8086	Intermediate Similarity	NPD1512	Approved
0.8065	Intermediate Similarity	NPD447	Suspended
0.8036	Intermediate Similarity	NPD7075	Discontinued
0.8025	Intermediate Similarity	NPD2532	Approved
0.8025	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD2534	Approved
0.8025	Intermediate Similarity	NPD2533	Approved
0.8024	Intermediate Similarity	NPD5402	Approved
0.8	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7768	Phase 2
0.7965	Intermediate Similarity	NPD6166	Phase 2
0.7965	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7054	Approved
0.7911	Intermediate Similarity	NPD2799	Discontinued
0.791	Intermediate Similarity	NPD8312	Approved
0.791	Intermediate Similarity	NPD8313	Approved
0.7904	Intermediate Similarity	NPD6801	Discontinued
0.7895	Intermediate Similarity	NPD6959	Discontinued
0.7892	Intermediate Similarity	NPD4380	Phase 2
0.7892	Intermediate Similarity	NPD6599	Discontinued
0.7888	Intermediate Similarity	NPD4628	Phase 3
0.7886	Intermediate Similarity	NPD7472	Approved
0.7886	Intermediate Similarity	NPD7074	Phase 3
0.7882	Intermediate Similarity	NPD6234	Discontinued
0.7875	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD2313	Discontinued
0.7862	Intermediate Similarity	NPD5404	Approved
0.7862	Intermediate Similarity	NPD5405	Approved
0.7862	Intermediate Similarity	NPD5406	Approved
0.7862	Intermediate Similarity	NPD5408	Approved
0.7831	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD3749	Approved
0.7805	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD1247	Approved
0.7778	Intermediate Similarity	NPD919	Approved
0.775	Intermediate Similarity	NPD1551	Phase 2
0.7744	Intermediate Similarity	NPD6799	Approved
0.774	Intermediate Similarity	NPD6797	Phase 2
0.7738	Intermediate Similarity	NPD7411	Suspended
0.7722	Intermediate Similarity	NPD1933	Approved
0.7722	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7251	Discontinued
0.7692	Intermediate Similarity	NPD37	Approved
0.7688	Intermediate Similarity	NPD3748	Approved
0.7688	Intermediate Similarity	NPD4308	Phase 3
0.768	Intermediate Similarity	NPD8150	Discontinued
0.7669	Intermediate Similarity	NPD7003	Approved
0.7669	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4966	Approved
0.7661	Intermediate Similarity	NPD4967	Phase 2
0.7661	Intermediate Similarity	NPD4965	Approved
0.7657	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7808	Phase 3
0.764	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD5403	Approved
0.7579	Intermediate Similarity	NPD7435	Discontinued
0.7578	Intermediate Similarity	NPD1510	Phase 2
0.7577	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD7783	Phase 2
0.7571	Intermediate Similarity	NPD7228	Approved
0.7562	Intermediate Similarity	NPD1607	Approved
0.756	Intermediate Similarity	NPD1653	Approved
0.7548	Intermediate Similarity	NPD1203	Approved
0.7547	Intermediate Similarity	NPD4060	Phase 1
0.7546	Intermediate Similarity	NPD1549	Phase 2
0.7532	Intermediate Similarity	NPD3764	Approved
0.7531	Intermediate Similarity	NPD2796	Approved
0.753	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6190	Approved
0.7513	Intermediate Similarity	NPD6779	Approved
0.7513	Intermediate Similarity	NPD6782	Approved
0.7513	Intermediate Similarity	NPD6777	Approved
0.7513	Intermediate Similarity	NPD6778	Approved
0.7513	Intermediate Similarity	NPD6776	Approved
0.7513	Intermediate Similarity	NPD6780	Approved
0.7513	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.7486	Intermediate Similarity	NPD7199	Phase 2
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7485	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5401	Approved
0.7485	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1283	Approved
0.7472	Intermediate Similarity	NPD3751	Discontinued
0.7469	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4625	Phase 3
0.7443	Intermediate Similarity	NPD5710	Approved
0.7443	Intermediate Similarity	NPD5711	Approved
0.7438	Intermediate Similarity	NPD4307	Phase 2
0.7438	Intermediate Similarity	NPD943	Approved
0.7438	Intermediate Similarity	NPD1240	Approved
0.7436	Intermediate Similarity	NPD2797	Approved
0.7435	Intermediate Similarity	NPD6823	Phase 2
0.7421	Intermediate Similarity	NPD411	Approved
0.7421	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6832	Phase 2
0.7405	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1243	Approved
0.7391	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD8127	Discontinued
0.7381	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2344	Approved
0.7374	Intermediate Similarity	NPD7177	Discontinued
0.7355	Intermediate Similarity	NPD9717	Approved
0.7349	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7874	Approved
0.7347	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD3787	Discontinued
0.7342	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6273	Approved
0.733	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1613	Approved
0.7329	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2979	Phase 3
0.7325	Intermediate Similarity	NPD1470	Approved
0.7321	Intermediate Similarity	NPD7390	Discontinued
0.7317	Intermediate Similarity	NPD2438	Suspended
0.7312	Intermediate Similarity	NPD3268	Approved
0.731	Intermediate Similarity	NPD7458	Discontinued
0.7308	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7697	Approved
0.7306	Intermediate Similarity	NPD7696	Phase 3
0.7306	Intermediate Similarity	NPD7698	Approved
0.7296	Intermediate Similarity	NPD8151	Discontinued
0.729	Intermediate Similarity	NPD1281	Approved
0.729	Intermediate Similarity	NPD1611	Approved
0.7289	Intermediate Similarity	NPD2800	Approved
0.7278	Intermediate Similarity	NPD2798	Approved
0.7273	Intermediate Similarity	NPD4626	Approved
0.7273	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7870	Phase 2
0.7268	Intermediate Similarity	NPD7871	Phase 2
0.7267	Intermediate Similarity	NPD6233	Phase 2
0.7262	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7033	Discontinued
0.7253	Intermediate Similarity	NPD5953	Discontinued
0.725	Intermediate Similarity	NPD3027	Phase 3
0.7249	Intermediate Similarity	NPD6534	Approved
0.7249	Intermediate Similarity	NPD6535	Approved
0.7247	Intermediate Similarity	NPD7229	Phase 3
0.7246	Intermediate Similarity	NPD8166	Discontinued
0.7245	Intermediate Similarity	NPD7701	Phase 2
0.7241	Intermediate Similarity	NPD8455	Phase 2
0.7238	Intermediate Similarity	NPD7286	Phase 2
0.7233	Intermediate Similarity	NPD9494	Approved
0.7215	Intermediate Similarity	NPD1164	Approved
0.7213	Intermediate Similarity	NPD7039	Approved
0.7213	Intermediate Similarity	NPD7038	Approved
0.7212	Intermediate Similarity	NPD6099	Approved
0.7212	Intermediate Similarity	NPD6100	Approved
0.7205	Intermediate Similarity	NPD6798	Discontinued
0.7205	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2309	Approved
0.72	Intermediate Similarity	NPD4288	Approved
0.7186	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6674	Discontinued
0.7179	Intermediate Similarity	NPD1201	Approved
0.7178	Intermediate Similarity	NPD6355	Discontinued
0.7174	Intermediate Similarity	NPD7549	Discontinued
0.7143	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7801	Approved
0.7135	Intermediate Similarity	NPD5049	Phase 3
0.7135	Intermediate Similarity	NPD1940	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