NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.08
Volume:	270.459
LogP:	3.661
LogD:	2.452
LogS:	-3.981
# Rotatable Bonds:	0
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.643
Synthetic Accessibility Score:	2.804
Fsp3:	0.267
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.9
MDCK Permeability:	2.2499227270600386e-05
Pgp-inhibitor:	0.045
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	98.12841796875%
Volume Distribution (VD):	0.56
Pgp-substrate:	3.981147289276123%

ADMET: Metabolism

CYP1A2-inhibitor:	0.917
CYP1A2-substrate:	0.508
CYP2C19-inhibitor:	0.246
CYP2C19-substrate:	0.089
CYP2C9-inhibitor:	0.742
CYP2C9-substrate:	0.796
CYP2D6-inhibitor:	0.634
CYP2D6-substrate:	0.247
CYP3A4-inhibitor:	0.251
CYP3A4-substrate:	0.148

ADMET: Excretion

Clearance (CL):	5.691
Half-life (T1/2):	0.516

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.36
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.563
Rat Oral Acute Toxicity:	0.255
Maximum Recommended Daily Dose:	0.285
Skin Sensitization:	0.888
Carcinogencity:	0.551
Eye Corrosion:	0.003
Eye Irritation:	0.785
Respiratory Toxicity:	0.238

Download Data

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

Natural Product: NPC173980

Natural Product ID:	NPC173980
*Common Name:**	4,9-Dihydroxy-Alpha-Lapachone
IUPAC Name:	(4S)-4,9-dihydroxy-2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione
Synonyms:
Standard InCHIKey:	KGIQEUTUJPXAKQ-VIFPVBQESA-N
Standard InCHI:	InChI=1S/C15H14O5/c1-15(2)6-9(17)11-12(18)7-4-3-5-8(16)10(7)13(19)14(11)20-15/h3-5,9,16-17H,6H2,1-2H3/t9-/m0/s1
SMILES:	O[C@H]1CC(C)(C)OC2=C1C(=O)c1c(C2=O)c(O)ccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506049
PubChem CID:	44575422
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	=	60.0	%	PMID[544762]
NPT2	Others	Unspecified		Activity	=	36.1	%	PMID[544762]
NPT2	Others	Unspecified		Activity	=	88.4	%	PMID[544762]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[544762]

☑ 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 NPC173980 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	317
0.1-0.2	1311
0.2-0.3	3182
0.3-0.4	8102
0.4-0.5	11094
0.5-0.6	5237
0.6-0.7	8275
0.7-0.8	4850
0.8-0.85	284
0.85-0.9	41
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9618	High Similarity	NPC171968
0.9237	High Similarity	NPC237225
0.9098	High Similarity	NPC198305
0.9084	High Similarity	NPC51037
0.9058	High Similarity	NPC103337
0.9058	High Similarity	NPC114620
0.8931	High Similarity	NPC310540
0.8921	High Similarity	NPC477408
0.8881	High Similarity	NPC136878
0.8824	High Similarity	NPC309430
0.8824	High Similarity	NPC477406
0.8811	High Similarity	NPC474630
0.8806	High Similarity	NPC165257
0.8797	High Similarity	NPC231774
0.8779	High Similarity	NPC65627
0.8777	High Similarity	NPC284184
0.8777	High Similarity	NPC301341
0.8741	High Similarity	NPC29932
0.8714	High Similarity	NPC61590
0.8712	High Similarity	NPC135062
0.8705	High Similarity	NPC315275
0.8699	High Similarity	NPC120171
0.8686	High Similarity	NPC110609
0.8686	High Similarity	NPC242358
0.8686	High Similarity	NPC246693
0.8676	High Similarity	NPC199253
0.8676	High Similarity	NPC136588
0.8662	High Similarity	NPC283292
0.8652	High Similarity	NPC295339
0.8647	High Similarity	NPC74507
0.8647	High Similarity	NPC234890
0.863	High Similarity	NPC94781
0.8623	High Similarity	NPC254603
0.8623	High Similarity	NPC52407
0.8613	High Similarity	NPC205360
0.8611	High Similarity	NPC477409
0.8611	High Similarity	NPC103910
0.8592	High Similarity	NPC156872
0.8571	High Similarity	NPC44378
0.8571	High Similarity	NPC232996
0.8571	High Similarity	NPC38158
0.8571	High Similarity	NPC280753
0.8562	High Similarity	NPC476821
0.8551	High Similarity	NPC88864
0.8551	High Similarity	NPC70622
0.855	High Similarity	NPC206778
0.855	High Similarity	NPC285829
0.854	High Similarity	NPC31799
0.8531	High Similarity	NPC257003
0.8519	High Similarity	NPC306765
0.8519	High Similarity	NPC1991
0.8519	High Similarity	NPC3224
0.8507	High Similarity	NPC68756
0.8507	High Similarity	NPC152525
0.8496	Intermediate Similarity	NPC307174
0.8483	Intermediate Similarity	NPC471906
0.8483	Intermediate Similarity	NPC79627
0.8467	Intermediate Similarity	NPC278928
0.8456	Intermediate Similarity	NPC205918
0.8444	Intermediate Similarity	NPC287473
0.8433	Intermediate Similarity	NPC375356
0.8425	Intermediate Similarity	NPC478160
0.8425	Intermediate Similarity	NPC478019
0.8421	Intermediate Similarity	NPC472889
0.8417	Intermediate Similarity	NPC17843
0.8414	Intermediate Similarity	NPC143898
0.8414	Intermediate Similarity	NPC21873
0.8409	Intermediate Similarity	NPC7151
0.8409	Intermediate Similarity	NPC473662
0.8409	Intermediate Similarity	NPC216297
0.8406	Intermediate Similarity	NPC27659
0.8403	Intermediate Similarity	NPC110810
0.8392	Intermediate Similarity	NPC299405
0.8392	Intermediate Similarity	NPC471602
0.8392	Intermediate Similarity	NPC29771
0.8392	Intermediate Similarity	NPC216312
0.8392	Intermediate Similarity	NPC476477
0.8392	Intermediate Similarity	NPC111422
0.8392	Intermediate Similarity	NPC306835
0.8392	Intermediate Similarity	NPC256463
0.8382	Intermediate Similarity	NPC96915
0.8382	Intermediate Similarity	NPC81135
0.838	Intermediate Similarity	NPC305060
0.8378	Intermediate Similarity	NPC112816
0.8369	Intermediate Similarity	NPC281513
0.8369	Intermediate Similarity	NPC22222
0.8367	Intermediate Similarity	NPC285122
0.8358	Intermediate Similarity	NPC164947
0.8358	Intermediate Similarity	NPC300274
0.8357	Intermediate Similarity	NPC193169
0.8357	Intermediate Similarity	NPC59459
0.8356	Intermediate Similarity	NPC475201
0.8345	Intermediate Similarity	NPC469520
0.8345	Intermediate Similarity	NPC474300
0.8345	Intermediate Similarity	NPC93015
0.8333	Intermediate Similarity	NPC220496
0.8333	Intermediate Similarity	NPC42262
0.8333	Intermediate Similarity	NPC91809
0.8333	Intermediate Similarity	NPC241349
0.8333	Intermediate Similarity	NPC37992
0.8333	Intermediate Similarity	NPC32749
0.8333	Intermediate Similarity	NPC34414
0.8333	Intermediate Similarity	NPC327916
0.8333	Intermediate Similarity	NPC147542
0.8333	Intermediate Similarity	NPC146647
0.8322	Intermediate Similarity	NPC84142
0.8322	Intermediate Similarity	NPC474310
0.8311	Intermediate Similarity	NPC472135
0.831	Intermediate Similarity	NPC86524
0.831	Intermediate Similarity	NPC474311
0.8309	Intermediate Similarity	NPC103540
0.8298	Intermediate Similarity	NPC50924
0.8289	Intermediate Similarity	NPC170189
0.8289	Intermediate Similarity	NPC314257
0.8289	Intermediate Similarity	NPC208173
0.8288	Intermediate Similarity	NPC478164
0.8288	Intermediate Similarity	NPC469885
0.8288	Intermediate Similarity	NPC476473
0.8286	Intermediate Similarity	NPC478190
0.8278	Intermediate Similarity	NPC115249
0.8276	Intermediate Similarity	NPC471444
0.8276	Intermediate Similarity	NPC305845
0.8276	Intermediate Similarity	NPC204045
0.8273	Intermediate Similarity	NPC475741
0.8273	Intermediate Similarity	NPC117609
0.8273	Intermediate Similarity	NPC55949
0.8267	Intermediate Similarity	NPC164762
0.8264	Intermediate Similarity	NPC190457
0.8261	Intermediate Similarity	NPC247250
0.8261	Intermediate Similarity	NPC767
0.8261	Intermediate Similarity	NPC282923
0.8258	Intermediate Similarity	NPC41567
0.8255	Intermediate Similarity	NPC142846
0.8244	Intermediate Similarity	NPC108288
0.8243	Intermediate Similarity	NPC300540
0.8239	Intermediate Similarity	NPC80035
0.8235	Intermediate Similarity	NPC142956
0.8231	Intermediate Similarity	NPC89664
0.8231	Intermediate Similarity	NPC244691
0.8231	Intermediate Similarity	NPC274085
0.8227	Intermediate Similarity	NPC225051
0.8227	Intermediate Similarity	NPC314048
0.8227	Intermediate Similarity	NPC263817
0.8224	Intermediate Similarity	NPC137301
0.8224	Intermediate Similarity	NPC312482
0.8224	Intermediate Similarity	NPC155686
0.8219	Intermediate Similarity	NPC135524
0.8219	Intermediate Similarity	NPC308572
0.8217	Intermediate Similarity	NPC470735
0.8217	Intermediate Similarity	NPC329647
0.8214	Intermediate Similarity	NPC205992
0.8214	Intermediate Similarity	NPC244699
0.8214	Intermediate Similarity	NPC477412
0.8212	Intermediate Similarity	NPC46882
0.8212	Intermediate Similarity	NPC132990
0.8201	Intermediate Similarity	NPC99731
0.82	Intermediate Similarity	NPC77325
0.82	Intermediate Similarity	NPC4423
0.8195	Intermediate Similarity	NPC232178
0.8194	Intermediate Similarity	NPC284495
0.8188	Intermediate Similarity	NPC252208
0.8188	Intermediate Similarity	NPC471530
0.8188	Intermediate Similarity	NPC470841
0.8188	Intermediate Similarity	NPC478018
0.8182	Intermediate Similarity	NPC141934
0.8182	Intermediate Similarity	NPC155211
0.8182	Intermediate Similarity	NPC317900
0.8182	Intermediate Similarity	NPC246466
0.8182	Intermediate Similarity	NPC476404
0.8182	Intermediate Similarity	NPC294300
0.8182	Intermediate Similarity	NPC29552
0.8176	Intermediate Similarity	NPC170055
0.8176	Intermediate Similarity	NPC28632
0.8175	Intermediate Similarity	NPC123506
0.817	Intermediate Similarity	NPC478133
0.817	Intermediate Similarity	NPC472890
0.817	Intermediate Similarity	NPC69043
0.817	Intermediate Similarity	NPC478230
0.817	Intermediate Similarity	NPC478221
0.817	Intermediate Similarity	NPC317585
0.8169	Intermediate Similarity	NPC44437
0.8169	Intermediate Similarity	NPC474097
0.8169	Intermediate Similarity	NPC202225
0.8158	Intermediate Similarity	NPC470340
0.8158	Intermediate Similarity	NPC184284
0.8158	Intermediate Similarity	NPC478224
0.8158	Intermediate Similarity	NPC76041
0.8156	Intermediate Similarity	NPC477407
0.8151	Intermediate Similarity	NPC149533
0.8146	Intermediate Similarity	NPC472891
0.8143	Intermediate Similarity	NPC147757
0.8141	Intermediate Similarity	NPC478134
0.8138	Intermediate Similarity	NPC26924
0.8133	Intermediate Similarity	NPC470479
0.8129	Intermediate Similarity	NPC48248
0.8129	Intermediate Similarity	NPC179898
0.8125	Intermediate Similarity	NPC264022
0.8125	Intermediate Similarity	NPC471452
0.8125	Intermediate Similarity	NPC475957
0.8125	Intermediate Similarity	NPC53414

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 NPC173980 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	892
0.2-0.3	1480
0.3-0.4	2674
0.4-0.5	2144
0.5-0.6	1174
0.6-0.7	415
0.7-0.8	89
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8309	Intermediate Similarity	NPD1470	Approved
0.8244	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD1201	Approved
0.7703	Intermediate Similarity	NPD2346	Discontinued
0.7687	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD3300	Phase 2
0.7613	Intermediate Similarity	NPD3226	Approved
0.7584	Intermediate Similarity	NPD1471	Phase 3
0.7582	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1510	Phase 2
0.7533	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD8150	Discontinued
0.7463	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4380	Phase 2
0.7417	Intermediate Similarity	NPD1549	Phase 2
0.7415	Intermediate Similarity	NPD943	Approved
0.7403	Intermediate Similarity	NPD7390	Discontinued
0.74	Intermediate Similarity	NPD2935	Discontinued
0.7397	Intermediate Similarity	NPD2313	Discontinued
0.7355	Intermediate Similarity	NPD2533	Approved
0.7355	Intermediate Similarity	NPD2534	Approved
0.7355	Intermediate Similarity	NPD2532	Approved
0.7351	Intermediate Similarity	NPD2344	Approved
0.7351	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD9493	Approved
0.7315	Intermediate Similarity	NPD1607	Approved
0.7312	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7819	Suspended
0.7308	Intermediate Similarity	NPD1512	Approved
0.7297	Intermediate Similarity	NPD1240	Approved
0.7285	Intermediate Similarity	NPD5408	Approved
0.7285	Intermediate Similarity	NPD5404	Approved
0.7285	Intermediate Similarity	NPD5405	Approved
0.7285	Intermediate Similarity	NPD5406	Approved
0.7284	Intermediate Similarity	NPD7075	Discontinued
0.7267	Intermediate Similarity	NPD5402	Approved
0.7256	Intermediate Similarity	NPD6959	Discontinued
0.7254	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1934	Approved
0.725	Intermediate Similarity	NPD6801	Discontinued
0.7246	Intermediate Similarity	NPD3751	Discontinued
0.7241	Intermediate Similarity	NPD2798	Approved
0.7235	Intermediate Similarity	NPD4955	Approved
0.7235	Intermediate Similarity	NPD36	Approved
0.7235	Intermediate Similarity	NPD5026	Approved
0.7235	Intermediate Similarity	NPD5028	Approved
0.7235	Intermediate Similarity	NPD4954	Approved
0.7235	Intermediate Similarity	NPD5034	Approved
0.7226	Intermediate Similarity	NPD7236	Approved
0.7222	Intermediate Similarity	NPD3882	Suspended
0.7212	Intermediate Similarity	NPD6232	Discontinued
0.7205	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7473	Discontinued
0.7179	Intermediate Similarity	NPD1511	Approved
0.7176	Intermediate Similarity	NPD5030	Phase 2
0.7172	Intermediate Similarity	NPD1164	Approved
0.7171	Intermediate Similarity	NPD2796	Approved
0.717	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2309	Approved
0.7134	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD447	Suspended
0.7126	Intermediate Similarity	NPD6166	Phase 2
0.7126	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6534	Approved
0.7119	Intermediate Similarity	NPD6535	Approved
0.7113	Intermediate Similarity	NPD2932	Approved
0.7111	Intermediate Similarity	NPD6781	Approved
0.7111	Intermediate Similarity	NPD9266	Approved
0.7111	Intermediate Similarity	NPD6778	Approved
0.7111	Intermediate Similarity	NPD6782	Approved
0.7111	Intermediate Similarity	NPD6780	Approved
0.7111	Intermediate Similarity	NPD6776	Approved
0.7111	Intermediate Similarity	NPD6779	Approved
0.7111	Intermediate Similarity	NPD74	Approved
0.7111	Intermediate Similarity	NPD6777	Approved
0.7105	Intermediate Similarity	NPD2799	Discontinued
0.7101	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2801	Approved
0.7097	Intermediate Similarity	NPD3750	Approved
0.7088	Intermediate Similarity	NPD7435	Discontinued
0.7083	Intermediate Similarity	NPD9717	Approved
0.7073	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5038	Approved
0.7069	Intermediate Similarity	NPD8434	Phase 2
0.7069	Intermediate Similarity	NPD5037	Approved
0.7068	Intermediate Similarity	NPD1237	Approved
0.7055	Intermediate Similarity	NPD3817	Phase 2
0.7055	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1203	Approved
0.7051	Intermediate Similarity	NPD6190	Approved
0.7047	Intermediate Similarity	NPD411	Approved
0.7047	Intermediate Similarity	NPD3764	Approved
0.7044	Intermediate Similarity	NPD5403	Approved
0.7042	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3818	Discontinued
0.7037	Intermediate Similarity	NPD9263	Approved
0.7037	Intermediate Similarity	NPD9264	Approved
0.7037	Intermediate Similarity	NPD6844	Discontinued
0.7037	Intermediate Similarity	NPD9267	Approved
0.7032	Intermediate Similarity	NPD2800	Approved
0.7025	Intermediate Similarity	NPD5401	Approved
0.7019	Intermediate Similarity	NPD6599	Discontinued
0.7018	Intermediate Similarity	NPD6797	Phase 2
0.7011	Intermediate Similarity	NPD5036	Approved
0.7	Intermediate Similarity	NPD7239	Suspended
0.7	Intermediate Similarity	NPD7699	Phase 2
0.7	Intermediate Similarity	NPD7700	Phase 2
0.6995	Remote Similarity	NPD7696	Phase 3
0.6995	Remote Similarity	NPD7698	Approved
0.6995	Remote Similarity	NPD7697	Approved
0.6994	Remote Similarity	NPD8312	Approved
0.6994	Remote Similarity	NPD8313	Approved
0.6993	Remote Similarity	NPD4308	Phase 3
0.6993	Remote Similarity	NPD3019	Approved
0.6977	Remote Similarity	NPD7251	Discontinued
0.6972	Remote Similarity	NPD9545	Approved
0.697	Remote Similarity	NPD3749	Approved
0.6962	Remote Similarity	NPD6799	Approved
0.6957	Remote Similarity	NPD7871	Phase 2
0.6957	Remote Similarity	NPD8320	Phase 1
0.6957	Remote Similarity	NPD8319	Approved
0.6957	Remote Similarity	NPD7870	Phase 2
0.6948	Remote Similarity	NPD1551	Phase 2
0.6946	Remote Similarity	NPD1247	Approved
0.6936	Remote Similarity	NPD7808	Phase 3
0.6936	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD230	Phase 1
0.6908	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5844	Phase 1
0.6893	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6663	Approved
0.6887	Remote Similarity	NPD520	Approved
0.6886	Remote Similarity	NPD5494	Approved
0.6884	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7033	Discontinued
0.6879	Remote Similarity	NPD8166	Discontinued
0.6879	Remote Similarity	NPD4628	Phase 3
0.6879	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6273	Approved
0.6875	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6213	Phase 3
0.6872	Remote Similarity	NPD6212	Phase 3
0.6871	Remote Similarity	NPD7411	Suspended
0.6862	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD7874	Approved
0.6846	Remote Similarity	NPD5736	Approved
0.6846	Remote Similarity	NPD9494	Approved
0.6845	Remote Similarity	NPD7701	Phase 2
0.6839	Remote Similarity	NPD6099	Approved
0.6839	Remote Similarity	NPD6100	Approved
0.6832	Remote Similarity	NPD920	Approved
0.6826	Remote Similarity	NPD919	Approved
0.6821	Remote Similarity	NPD3268	Approved
0.6809	Remote Similarity	NPD9281	Approved
0.6805	Remote Similarity	NPD3787	Discontinued
0.6805	Remote Similarity	NPD5711	Approved
0.6805	Remote Similarity	NPD5710	Approved
0.6802	Remote Similarity	NPD7054	Approved
0.68	Remote Similarity	NPD6832	Phase 2
0.68	Remote Similarity	NPD5035	Approved
0.6788	Remote Similarity	NPD5760	Phase 2
0.6788	Remote Similarity	NPD5761	Phase 2
0.6782	Remote Similarity	NPD6559	Discontinued
0.6782	Remote Similarity	NPD5027	Approved
0.6782	Remote Similarity	NPD5029	Approved
0.6782	Remote Similarity	NPD5031	Approved
0.6779	Remote Similarity	NPD1019	Discontinued
0.6774	Remote Similarity	NPD3748	Approved
0.6772	Remote Similarity	NPD7003	Approved
0.6763	Remote Similarity	NPD7472	Approved
0.6763	Remote Similarity	NPD7074	Phase 3
0.6757	Remote Similarity	NPD1283	Approved
0.6757	Remote Similarity	NPD1876	Approved
0.6748	Remote Similarity	NPD7458	Discontinued
0.6741	Remote Similarity	NPD9261	Approved
0.6738	Remote Similarity	NPD1241	Discontinued
0.6737	Remote Similarity	NPD7801	Approved
0.6735	Remote Similarity	NPD3972	Approved
0.6732	Remote Similarity	NPD4307	Phase 2
0.6732	Remote Similarity	NPD4060	Phase 1
0.6725	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2797	Approved
0.6708	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7058	Phase 2
0.6707	Remote Similarity	NPD7768	Phase 2
0.6707	Remote Similarity	NPD7057	Phase 3
0.6707	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1651	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