NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.12
Volume:	266.942
LogP:	1.121
LogD:	1.292
LogS:	-2.522
# Rotatable Bonds:	0
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.743
Synthetic Accessibility Score:	4.008
Fsp3:	0.533
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:	-4.621
MDCK Permeability:	1.8033406377071515e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.409

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.448
Plasma Protein Binding (PPB):	67.25982666015625%
Volume Distribution (VD):	1.484
Pgp-substrate:	24.934368133544922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.082
CYP1A2-substrate:	0.223
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.601
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.696
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.29
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.284

ADMET: Excretion

Clearance (CL):	4.292
Half-life (T1/2):	0.247

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.38
Drug-inuced Liver Injury (DILI):	0.335
AMES Toxicity:	0.086
Rat Oral Acute Toxicity:	0.39
Maximum Recommended Daily Dose:	0.061
Skin Sensitization:	0.073
Carcinogencity:	0.055
Eye Corrosion:	0.008
Eye Irritation:	0.172
Respiratory Toxicity:	0.192

Download Data

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

Natural Product: NPC262819

Natural Product ID:	NPC262819
*Common Name:**	(4S,4Ar,10R,10Ar)-4,10-Dihydroxy-2,2-Dimethyl-4,4A,10,10A-Tetrahydro-3H-Benzo[G]Chromen-5-One
IUPAC Name:	(4S,4aR,10R,10aR)-4,10-dihydroxy-2,2-dimethyl-4,4a,10,10a-tetrahydro-3H-benzo[g]chromen-5-one
Synonyms:
Standard InCHIKey:	QSWYLDYQGGURJS-CDGCEXEKSA-N
Standard InCHI:	InChI=1S/C15H18O4/c1-15(2)7-10(16)11-12(17)8-5-3-4-6-9(8)13(18)14(11)19-15/h3-6,10-11,13-14,16,18H,7H2,1-2H3/t10-,11-,13+,14+/m0/s1
SMILES:	CC1(C)C[C@@H]([C@H]2C(=O)c3ccccc3[C@H]([C@@H]2O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512313
PubChem CID:	10332913
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	stem bark	Medicinal Plant Garden, College of Pharmacy, Ewha Womans University	2013-DEC	PMID[28787158]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599262]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	5

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[507804]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[507804]
NPT2	Others	Unspecified		Activity	=	32.9	%	PMID[507804]
NPT2	Others	Unspecified		Activity	=	57.3	%	PMID[507804]
NPT2	Others	Unspecified		Activity	=	93.8	%	PMID[507804]

☑ 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 NPC262819 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	275
0.1-0.2	1036
0.2-0.3	2160
0.3-0.4	5151
0.4-0.5	10483
0.5-0.6	10540
0.6-0.7	10479
0.7-0.8	2461
0.8-0.85	110
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8444	Intermediate Similarity	NPC477896
0.8429	Intermediate Similarity	NPC127857
0.8397	Intermediate Similarity	NPC81135
0.8392	Intermediate Similarity	NPC94781
0.8392	Intermediate Similarity	NPC197037
0.838	Intermediate Similarity	NPC60509
0.838	Intermediate Similarity	NPC250046
0.838	Intermediate Similarity	NPC81698
0.8359	Intermediate Similarity	NPC472981
0.8333	Intermediate Similarity	NPC280753
0.8333	Intermediate Similarity	NPC44378
0.8322	Intermediate Similarity	NPC165260
0.8322	Intermediate Similarity	NPC7095
0.8322	Intermediate Similarity	NPC161239
0.8322	Intermediate Similarity	NPC198455
0.8322	Intermediate Similarity	NPC91730
0.8309	Intermediate Similarity	NPC477893
0.8286	Intermediate Similarity	NPC477894
0.8276	Intermediate Similarity	NPC134685
0.8276	Intermediate Similarity	NPC11588
0.8276	Intermediate Similarity	NPC229545
0.8276	Intermediate Similarity	NPC248265
0.8273	Intermediate Similarity	NPC77493
0.8264	Intermediate Similarity	NPC471103
0.8252	Intermediate Similarity	NPC285122
0.8239	Intermediate Similarity	NPC477737
0.8231	Intermediate Similarity	NPC65627
0.8219	Intermediate Similarity	NPC205918
0.8219	Intermediate Similarity	NPC155329
0.8219	Intermediate Similarity	NPC259144
0.8219	Intermediate Similarity	NPC21410
0.8219	Intermediate Similarity	NPC114357
0.8219	Intermediate Similarity	NPC473670
0.8207	Intermediate Similarity	NPC477905
0.8207	Intermediate Similarity	NPC472548
0.8195	Intermediate Similarity	NPC51448
0.8195	Intermediate Similarity	NPC115797
0.8194	Intermediate Similarity	NPC112216
0.8182	Intermediate Similarity	NPC170055
0.8182	Intermediate Similarity	NPC217918
0.8176	Intermediate Similarity	NPC314257
0.8175	Intermediate Similarity	NPC23894
0.8151	Intermediate Similarity	NPC237549
0.8151	Intermediate Similarity	NPC256142
0.8151	Intermediate Similarity	NPC257213
0.8151	Intermediate Similarity	NPC1173
0.8151	Intermediate Similarity	NPC133430
0.8151	Intermediate Similarity	NPC472022
0.8151	Intermediate Similarity	NPC249471
0.8151	Intermediate Similarity	NPC219419
0.8151	Intermediate Similarity	NPC472005
0.8151	Intermediate Similarity	NPC472030
0.8151	Intermediate Similarity	NPC473414
0.8151	Intermediate Similarity	NPC158333
0.8151	Intermediate Similarity	NPC265395
0.8151	Intermediate Similarity	NPC242262
0.8151	Intermediate Similarity	NPC304876
0.8151	Intermediate Similarity	NPC469477
0.8148	Intermediate Similarity	NPC471334
0.8138	Intermediate Similarity	NPC306799
0.8138	Intermediate Similarity	NPC101043
0.8138	Intermediate Similarity	NPC51602
0.8125	Intermediate Similarity	NPC136878
0.812	Intermediate Similarity	NPC169913
0.8115	Intermediate Similarity	NPC211439
0.8112	Intermediate Similarity	NPC469513
0.8112	Intermediate Similarity	NPC218866
0.8112	Intermediate Similarity	NPC84568
0.8112	Intermediate Similarity	NPC300684
0.8112	Intermediate Similarity	NPC48130
0.8108	Intermediate Similarity	NPC469417
0.8095	Intermediate Similarity	NPC472549
0.8095	Intermediate Similarity	NPC228204
0.8095	Intermediate Similarity	NPC26033
0.8095	Intermediate Similarity	NPC112523
0.8095	Intermediate Similarity	NPC114410
0.8095	Intermediate Similarity	NPC251139
0.8085	Intermediate Similarity	NPC182869
0.8082	Intermediate Similarity	NPC120171
0.8074	Intermediate Similarity	NPC27712
0.8071	Intermediate Similarity	NPC275592
0.8071	Intermediate Similarity	NPC472547
0.8071	Intermediate Similarity	NPC173980
0.8071	Intermediate Similarity	NPC100913
0.8058	Intermediate Similarity	NPC39549
0.8056	Intermediate Similarity	NPC132652
0.8045	Intermediate Similarity	NPC294050
0.8045	Intermediate Similarity	NPC236405
0.8045	Intermediate Similarity	NPC328997
0.8045	Intermediate Similarity	NPC275576
0.8041	Intermediate Similarity	NPC106895
0.8029	Intermediate Similarity	NPC144257
0.8028	Intermediate Similarity	NPC477468
0.8027	Intermediate Similarity	NPC77719
0.8014	Intermediate Similarity	NPC87448
0.8014	Intermediate Similarity	NPC472576
0.8014	Intermediate Similarity	NPC291599
0.8014	Intermediate Similarity	NPC27377
0.8014	Intermediate Similarity	NPC97947
0.8014	Intermediate Similarity	NPC41481
0.8014	Intermediate Similarity	NPC118080
0.8014	Intermediate Similarity	NPC213567
0.8	Intermediate Similarity	NPC471970
0.8	Intermediate Similarity	NPC273798
0.8	Intermediate Similarity	NPC247250
0.8	Intermediate Similarity	NPC767
0.7987	Intermediate Similarity	NPC469771
0.7986	Intermediate Similarity	NPC29932
0.7986	Intermediate Similarity	NPC472545
0.7986	Intermediate Similarity	NPC472551
0.7973	Intermediate Similarity	NPC473632
0.7973	Intermediate Similarity	NPC282239
0.7973	Intermediate Similarity	NPC132599
0.7973	Intermediate Similarity	NPC469730
0.7972	Intermediate Similarity	NPC38696
0.7971	Intermediate Similarity	NPC126516
0.7971	Intermediate Similarity	NPC329913
0.7971	Intermediate Similarity	NPC310662
0.797	Intermediate Similarity	NPC74507
0.797	Intermediate Similarity	NPC234890
0.7959	Intermediate Similarity	NPC474310
0.7958	Intermediate Similarity	NPC34012
0.7955	Intermediate Similarity	NPC223351
0.7953	Intermediate Similarity	NPC186933
0.7943	Intermediate Similarity	NPC90614
0.7943	Intermediate Similarity	NPC171207
0.7943	Intermediate Similarity	NPC183270
0.7943	Intermediate Similarity	NPC477904
0.7943	Intermediate Similarity	NPC97667
0.7933	Intermediate Similarity	NPC469399
0.7929	Intermediate Similarity	NPC315275
0.7926	Intermediate Similarity	NPC316553
0.7923	Intermediate Similarity	NPC476645
0.792	Intermediate Similarity	NPC474057
0.7919	Intermediate Similarity	NPC11410
0.7919	Intermediate Similarity	NPC180944
0.7919	Intermediate Similarity	NPC217091
0.7917	Intermediate Similarity	NPC472556
0.7917	Intermediate Similarity	NPC471100
0.7917	Intermediate Similarity	NPC471107
0.7914	Intermediate Similarity	NPC474659
0.7914	Intermediate Similarity	NPC202225
0.7908	Intermediate Similarity	NPC471134
0.7908	Intermediate Similarity	NPC471493
0.7908	Intermediate Similarity	NPC477627
0.7905	Intermediate Similarity	NPC146310
0.7902	Intermediate Similarity	NPC95449
0.7902	Intermediate Similarity	NPC91703
0.7899	Intermediate Similarity	NPC17843
0.7895	Intermediate Similarity	NPC477188
0.7895	Intermediate Similarity	NPC43304
0.7895	Intermediate Similarity	NPC477190
0.7895	Intermediate Similarity	NPC85511
0.7891	Intermediate Similarity	NPC62138
0.7891	Intermediate Similarity	NPC470153
0.7891	Intermediate Similarity	NPC132810
0.7887	Intermediate Similarity	NPC114620
0.7887	Intermediate Similarity	NPC103337
0.7887	Intermediate Similarity	NPC16912
0.7886	Intermediate Similarity	NPC25385
0.7886	Intermediate Similarity	NPC475905
0.7886	Intermediate Similarity	NPC193640
0.7881	Intermediate Similarity	NPC164427
0.7874	Intermediate Similarity	NPC196673
0.7872	Intermediate Similarity	NPC156393
0.7867	Intermediate Similarity	NPC472393
0.7863	Intermediate Similarity	NPC105709
0.7862	Intermediate Similarity	NPC474241
0.7862	Intermediate Similarity	NPC469856
0.7862	Intermediate Similarity	NPC79627
0.7862	Intermediate Similarity	NPC103910
0.7862	Intermediate Similarity	NPC469854
0.7857	Intermediate Similarity	NPC472372
0.7857	Intermediate Similarity	NPC472374
0.7852	Intermediate Similarity	NPC5115
0.7852	Intermediate Similarity	NPC46564
0.7852	Intermediate Similarity	NPC473611
0.7852	Intermediate Similarity	NPC474106
0.7852	Intermediate Similarity	NPC207346
0.7852	Intermediate Similarity	NPC146239
0.7847	Intermediate Similarity	NPC475122
0.7847	Intermediate Similarity	NPC241951
0.7847	Intermediate Similarity	NPC471971
0.7847	Intermediate Similarity	NPC475759
0.7847	Intermediate Similarity	NPC30846
0.7847	Intermediate Similarity	NPC469855
0.7847	Intermediate Similarity	NPC470152
0.7847	Intermediate Similarity	NPC471972
0.7843	Intermediate Similarity	NPC66193
0.7842	Intermediate Similarity	NPC52407
0.7838	Intermediate Similarity	NPC478219
0.7832	Intermediate Similarity	NPC471853
0.7823	Intermediate Similarity	NPC81835
0.7817	Intermediate Similarity	NPC474250
0.7815	Intermediate Similarity	NPC3449
0.7815	Intermediate Similarity	NPC175192
0.7815	Intermediate Similarity	NPC471102
0.78	Intermediate Similarity	NPC470337
0.78	Intermediate Similarity	NPC470338
0.78	Intermediate Similarity	NPC470340

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 NPC262819 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	744
0.2-0.3	1349
0.3-0.4	2648
0.4-0.5	2387
0.5-0.6	1304
0.6-0.7	453
0.7-0.8	24
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
0.7778	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD7236	Approved
0.7538	Intermediate Similarity	NPD2629	Approved
0.7481	Intermediate Similarity	NPD3317	Approved
0.7442	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1237	Approved
0.7429	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7239	Suspended
0.7391	Intermediate Similarity	NPD1470	Approved
0.7333	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4380	Phase 2
0.731	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5951	Approved
0.7256	Intermediate Similarity	NPD8368	Discontinued
0.7246	Intermediate Similarity	NPD8150	Discontinued
0.7226	Intermediate Similarity	NPD1201	Approved
0.7219	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2346	Discontinued
0.72	Intermediate Similarity	NPD3300	Phase 2
0.7179	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD943	Approved
0.7143	Intermediate Similarity	NPD8434	Phase 2
0.7126	Intermediate Similarity	NPD8407	Phase 2
0.7117	Intermediate Similarity	NPD7799	Discontinued
0.7115	Intermediate Similarity	NPD1934	Approved
0.7099	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7058	Phase 2
0.7089	Intermediate Similarity	NPD7057	Phase 3
0.7077	Intermediate Similarity	NPD2182	Approved
0.7075	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4628	Phase 3
0.7063	Intermediate Similarity	NPD7008	Discontinued
0.7059	Intermediate Similarity	NPD8361	Approved
0.7059	Intermediate Similarity	NPD8360	Approved
0.705	Intermediate Similarity	NPD4878	Approved
0.7037	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5844	Phase 1
0.6966	Remote Similarity	NPD7961	Discontinued
0.6962	Remote Similarity	NPD7819	Suspended
0.6962	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8435	Approved
0.6957	Remote Similarity	NPD5126	Approved
0.6957	Remote Similarity	NPD5125	Phase 3
0.6957	Remote Similarity	NPD5494	Approved
0.6957	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8166	Discontinued
0.6953	Remote Similarity	NPD1930	Approved
0.6953	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD1929	Approved
0.6951	Remote Similarity	NPD7473	Discontinued
0.6947	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7075	Discontinued
0.6933	Remote Similarity	NPD1549	Phase 2
0.6928	Remote Similarity	NPD7390	Discontinued
0.6923	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD5406	Approved
0.6913	Remote Similarity	NPD5408	Approved
0.6913	Remote Similarity	NPD5405	Approved
0.6913	Remote Similarity	NPD5404	Approved
0.6908	Remote Similarity	NPD6190	Approved
0.6899	Remote Similarity	NPD164	Approved
0.6897	Remote Similarity	NPD6534	Approved
0.6897	Remote Similarity	NPD6535	Approved
0.689	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6166	Phase 2
0.6889	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5157	Phase 1
0.6879	Remote Similarity	NPD5159	Phase 2
0.6879	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6232	Discontinued
0.6867	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1471	Phase 3
0.6864	Remote Similarity	NPD8313	Approved
0.6864	Remote Similarity	NPD8312	Approved
0.6861	Remote Similarity	NPD7610	Discontinued
0.6855	Remote Similarity	NPD5761	Phase 2
0.6855	Remote Similarity	NPD2801	Approved
0.6855	Remote Similarity	NPD5760	Phase 2
0.685	Remote Similarity	NPD2066	Phase 3
0.6846	Remote Similarity	NPD5048	Discontinued
0.6846	Remote Similarity	NPD2799	Discontinued
0.6846	Remote Similarity	NPD1510	Phase 2
0.6846	Remote Similarity	NPD7305	Phase 1
0.6845	Remote Similarity	NPD5030	Phase 2
0.6842	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4198	Discontinued
0.6835	Remote Similarity	NPD3019	Approved
0.6835	Remote Similarity	NPD5306	Approved
0.6835	Remote Similarity	NPD5305	Approved
0.6835	Remote Similarity	NPD2932	Approved
0.6822	Remote Similarity	NPD6647	Phase 2
0.6818	Remote Similarity	NPD8485	Approved
0.6815	Remote Similarity	NPD7458	Discontinued
0.6815	Remote Similarity	NPD3226	Approved
0.6815	Remote Similarity	NPD6010	Discontinued
0.6813	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6959	Discontinued
0.6807	Remote Similarity	NPD3818	Discontinued
0.6807	Remote Similarity	NPD3751	Discontinued
0.6805	Remote Similarity	NPD4955	Approved
0.6805	Remote Similarity	NPD36	Approved
0.6805	Remote Similarity	NPD5026	Approved
0.6805	Remote Similarity	NPD4954	Approved
0.6805	Remote Similarity	NPD5028	Approved
0.6805	Remote Similarity	NPD5034	Approved
0.68	Remote Similarity	NPD2935	Discontinued
0.6792	Remote Similarity	NPD6801	Discontinued
0.6786	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3764	Approved
0.6781	Remote Similarity	NPD2313	Discontinued
0.678	Remote Similarity	NPD7699	Phase 2
0.678	Remote Similarity	NPD7700	Phase 2
0.6774	Remote Similarity	NPD2532	Approved
0.6774	Remote Similarity	NPD2534	Approved
0.6774	Remote Similarity	NPD2533	Approved
0.6774	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD9495	Approved
0.677	Remote Similarity	NPD3882	Suspended
0.677	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD230	Phase 1
0.6743	Remote Similarity	NPD6212	Phase 3
0.6743	Remote Similarity	NPD6213	Phase 3
0.6743	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD4807	Approved
0.6738	Remote Similarity	NPD4806	Approved
0.6738	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2798	Approved
0.6735	Remote Similarity	NPD6663	Approved
0.6733	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6273	Approved
0.6726	Remote Similarity	NPD7074	Phase 3
0.6711	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1607	Approved
0.671	Remote Similarity	NPD1511	Approved
0.6709	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD6777	Approved
0.6704	Remote Similarity	NPD6781	Approved
0.6704	Remote Similarity	NPD6779	Approved
0.6704	Remote Similarity	NPD6780	Approved
0.6704	Remote Similarity	NPD6778	Approved
0.6704	Remote Similarity	NPD6782	Approved
0.6704	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD6776	Approved
0.6692	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.669	Remote Similarity	NPD9494	Approved
0.669	Remote Similarity	NPD5736	Approved
0.6689	Remote Similarity	NPD2796	Approved
0.6689	Remote Similarity	NPD1240	Approved
0.6686	Remote Similarity	NPD5036	Approved
0.6667	Remote Similarity	NPD7054	Approved
0.6667	Remote Similarity	NPD3787	Discontinued
0.6667	Remote Similarity	NPD3094	Phase 2
0.6667	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1164	Approved
0.6667	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4136	Approved
0.6667	Remote Similarity	NPD4106	Approved
0.6667	Remote Similarity	NPD4135	Approved
0.6667	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6599	Discontinued
0.6648	Remote Similarity	NPD8320	Phase 1
0.6648	Remote Similarity	NPD8319	Approved
0.6647	Remote Similarity	NPD5038	Approved
0.6647	Remote Similarity	NPD6559	Discontinued
0.6647	Remote Similarity	NPD5037	Approved
0.6645	Remote Similarity	NPD2344	Approved
0.6644	Remote Similarity	NPD5203	Approved
0.6644	Remote Similarity	NPD4620	Approved
0.6644	Remote Similarity	NPD447	Suspended
0.6644	Remote Similarity	NPD5201	Approved
0.6644	Remote Similarity	NPD4617	Approved
0.6627	Remote Similarity	NPD7472	Approved
0.6625	Remote Similarity	NPD7411	Suspended
0.6624	Remote Similarity	NPD1512	Approved
0.6623	Remote Similarity	NPD7003	Approved
0.6621	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6085	Phase 2
0.6615	Remote Similarity	NPD1932	Approved
0.6605	Remote Similarity	NPD5402	Approved
0.6605	Remote Similarity	NPD3817	Phase 2
0.6603	Remote Similarity	NPD6799	Approved
0.6601	Remote Similarity	NPD2424	Discontinued
0.6593	Remote Similarity	NPD7435	Discontinued
0.6589	Remote Similarity	NPD1238	Approved
0.6588	Remote Similarity	NPD6797	Phase 2
0.6584	Remote Similarity	NPD37	Approved
0.6577	Remote Similarity	NPD5121	Approved
0.6577	Remote Similarity	NPD5120	Approved
0.6577	Remote Similarity	NPD5119	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