NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	204.04
Volume:	195.122
LogP:	1.73
LogD:	1.701
LogS:	-3.219
# Rotatable Bonds:	0
TPSA:	66.9
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.638
Synthetic Accessibility Score:	3.773
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.654
MDCK Permeability:	2.3987360691535287e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.047

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.408
Plasma Protein Binding (PPB):	81.61470794677734%
Volume Distribution (VD):	0.866
Pgp-substrate:	13.963810920715332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.55
CYP1A2-substrate:	0.745
CYP2C19-inhibitor:	0.081
CYP2C19-substrate:	0.448
CYP2C9-inhibitor:	0.085
CYP2C9-substrate:	0.494
CYP2D6-inhibitor:	0.071
CYP2D6-substrate:	0.382
CYP3A4-inhibitor:	0.262
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	5.898
Half-life (T1/2):	0.189

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.113
Drug-inuced Liver Injury (DILI):	0.824
AMES Toxicity:	0.845
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.75
Carcinogencity:	0.608
Eye Corrosion:	0.017
Eye Irritation:	0.84
Respiratory Toxicity:	0.454

Download Data

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

Natural Product: NPC114620

Natural Product ID:	NPC114620
*Common Name:**	3-Hydroxy-7A-Methyl-1Ah-Naphtho[2,3-B]Oxirene-2,7-Dione
IUPAC Name:	3-hydroxy-7a-methyl-1aH-naphtho[2,3-b]oxirene-2,7-dione
Synonyms:
Standard InCHIKey:	XYOABSOIKCDDDO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H8O4/c1-11-9(14)5-3-2-4-6(12)7(5)8(13)10(11)15-11/h2-4,10,12H,1H3
SMILES:	Oc1cccc2c1C(=O)C1OC1(C2=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3217787
PubChem CID:	71348507
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	bark	Indonesia	n.a.	PMID[15270571]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22313254]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16657	Diospyros maritima	Species	Ebenaceae	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
IC50	1
Others	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		Stability	=	64.0	%	PMID[486716]
NPT35	Others	n.a.		Activity	=	1.6	uM	PMID[486716]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	22800.0	nM	PMID[486716]

☑ 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 NPC114620 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	356
0.1-0.2	1487
0.2-0.3	3284
0.3-0.4	8621
0.4-0.5	10576
0.5-0.6	5588
0.6-0.7	8184
0.7-0.8	4324
0.8-0.85	243
0.85-0.9	30
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC103337
0.9296	High Similarity	NPC120171
0.9058	High Similarity	NPC173980
0.8971	High Similarity	NPC171968
0.8958	High Similarity	NPC94781
0.8936	High Similarity	NPC308572
0.8904	High Similarity	NPC205918
0.8897	High Similarity	NPC280753
0.8897	High Similarity	NPC309430
0.8897	High Similarity	NPC44378
0.8889	High Similarity	NPC472135
0.8881	High Similarity	NPC165257
0.8881	High Similarity	NPC237225
0.8872	High Similarity	NPC231774
0.8828	High Similarity	NPC142846
0.8811	High Similarity	NPC29932
0.8777	High Similarity	NPC38158
0.8759	High Similarity	NPC215593
0.8759	High Similarity	NPC476821
0.875	High Similarity	NPC198305
0.8731	High Similarity	NPC51037
0.8725	High Similarity	NPC314257
0.8722	High Similarity	NPC310540
0.8696	High Similarity	NPC254603
0.869	High Similarity	NPC472134
0.869	High Similarity	NPC136878
0.8623	High Similarity	NPC246693
0.8623	High Similarity	NPC88864
0.8623	High Similarity	NPC70622
0.8623	High Similarity	NPC110609
0.8623	High Similarity	NPC17843
0.8623	High Similarity	NPC242358
0.8621	High Similarity	NPC474630
0.8613	High Similarity	NPC475741
0.8603	High Similarity	NPC767
0.8603	High Similarity	NPC247250
0.8601	High Similarity	NPC257003
0.86	High Similarity	NPC478133
0.8593	High Similarity	NPC3224
0.8593	High Similarity	NPC1991
0.8592	High Similarity	NPC306835
0.8592	High Similarity	NPC471602
0.8592	High Similarity	NPC256463
0.8592	High Similarity	NPC476477
0.8592	High Similarity	NPC216312
0.8592	High Similarity	NPC29771
0.8592	High Similarity	NPC111422
0.8592	High Similarity	NPC299405
0.8582	High Similarity	NPC234890
0.8582	High Similarity	NPC74507
0.8561	High Similarity	NPC52407
0.8552	High Similarity	NPC477409
0.8552	High Similarity	NPC471906
0.8542	High Similarity	NPC474300
0.854	High Similarity	NPC99731
0.854	High Similarity	NPC278928
0.8531	High Similarity	NPC147542
0.8531	High Similarity	NPC37992
0.8531	High Similarity	NPC327916
0.8531	High Similarity	NPC32749
0.8531	High Similarity	NPC220496
0.8531	High Similarity	NPC42262
0.8531	High Similarity	NPC241349
0.8521	High Similarity	NPC61590
0.8519	High Similarity	NPC103540
0.8511	High Similarity	NPC315275
0.8511	High Similarity	NPC86524
0.8489	Intermediate Similarity	NPC477406
0.8489	Intermediate Similarity	NPC478190
0.8483	Intermediate Similarity	NPC354984
0.8483	Intermediate Similarity	NPC143898
0.8483	Intermediate Similarity	NPC476473
0.8478	Intermediate Similarity	NPC136588
0.8478	Intermediate Similarity	NPC199253
0.8472	Intermediate Similarity	NPC471444
0.8467	Intermediate Similarity	NPC282923
0.8462	Intermediate Similarity	NPC477408
0.8462	Intermediate Similarity	NPC26924
0.8462	Intermediate Similarity	NPC295339
0.8444	Intermediate Similarity	NPC152525
0.8444	Intermediate Similarity	NPC68756
0.8442	Intermediate Similarity	NPC478134
0.8435	Intermediate Similarity	NPC285122
0.8429	Intermediate Similarity	NPC193169
0.8429	Intermediate Similarity	NPC314048
0.8425	Intermediate Similarity	NPC79627
0.8417	Intermediate Similarity	NPC205992
0.8403	Intermediate Similarity	NPC315578
0.8403	Intermediate Similarity	NPC156872
0.8397	Intermediate Similarity	NPC472049
0.8392	Intermediate Similarity	NPC13715
0.8389	Intermediate Similarity	NPC226578
0.8389	Intermediate Similarity	NPC474310
0.8382	Intermediate Similarity	NPC287473
0.838	Intermediate Similarity	NPC141934
0.8378	Intermediate Similarity	NPC119767
0.837	Intermediate Similarity	NPC375356
0.8369	Intermediate Similarity	NPC44437
0.8366	Intermediate Similarity	NPC473282
0.8366	Intermediate Similarity	NPC476404
0.8366	Intermediate Similarity	NPC294300
0.8366	Intermediate Similarity	NPC104380
0.8366	Intermediate Similarity	NPC317900
0.8366	Intermediate Similarity	NPC217602
0.8357	Intermediate Similarity	NPC477407
0.8346	Intermediate Similarity	NPC216297
0.8346	Intermediate Similarity	NPC473662
0.8346	Intermediate Similarity	NPC285829
0.8346	Intermediate Similarity	NPC7151
0.8346	Intermediate Similarity	NPC206778
0.8345	Intermediate Similarity	NPC283292
0.8345	Intermediate Similarity	NPC110810
0.8345	Intermediate Similarity	NPC305845
0.8345	Intermediate Similarity	NPC147757
0.8345	Intermediate Similarity	NPC204045
0.8333	Intermediate Similarity	NPC56204
0.8333	Intermediate Similarity	NPC190457
0.8333	Intermediate Similarity	NPC52358
0.8322	Intermediate Similarity	NPC53206
0.8322	Intermediate Similarity	NPC305060
0.8322	Intermediate Similarity	NPC53414
0.8322	Intermediate Similarity	NPC112816
0.8322	Intermediate Similarity	NPC470479
0.8321	Intermediate Similarity	NPC96915
0.8321	Intermediate Similarity	NPC306765
0.8311	Intermediate Similarity	NPC470570
0.831	Intermediate Similarity	NPC27407
0.831	Intermediate Similarity	NPC80035
0.8299	Intermediate Similarity	NPC274085
0.8299	Intermediate Similarity	NPC89664
0.8299	Intermediate Similarity	NPC193703
0.8299	Intermediate Similarity	NPC103910
0.8299	Intermediate Similarity	NPC21599
0.8299	Intermediate Similarity	NPC48762
0.8299	Intermediate Similarity	NPC244691
0.8296	Intermediate Similarity	NPC300274
0.8296	Intermediate Similarity	NPC307174
0.8289	Intermediate Similarity	NPC182921
0.8289	Intermediate Similarity	NPC218870
0.8289	Intermediate Similarity	NPC474824
0.8289	Intermediate Similarity	NPC470408
0.8288	Intermediate Similarity	NPC135524
0.8288	Intermediate Similarity	NPC469520
0.8286	Intermediate Similarity	NPC205360
0.828	Intermediate Similarity	NPC470735
0.828	Intermediate Similarity	NPC329647
0.8267	Intermediate Similarity	NPC478219
0.8264	Intermediate Similarity	NPC221104
0.8264	Intermediate Similarity	NPC416
0.8264	Intermediate Similarity	NPC61398
0.8258	Intermediate Similarity	NPC284495
0.8255	Intermediate Similarity	NPC5568
0.8255	Intermediate Similarity	NPC252208
0.8252	Intermediate Similarity	NPC254847
0.8252	Intermediate Similarity	NPC474311
0.8252	Intermediate Similarity	NPC291454
0.8252	Intermediate Similarity	NPC232996
0.8243	Intermediate Similarity	NPC28632
0.8243	Intermediate Similarity	NPC170055
0.8243	Intermediate Similarity	NPC34482
0.8239	Intermediate Similarity	NPC288089
0.8239	Intermediate Similarity	NPC50924
0.8239	Intermediate Similarity	NPC166480
0.8239	Intermediate Similarity	NPC282780
0.8235	Intermediate Similarity	NPC135062
0.8231	Intermediate Similarity	NPC21873
0.8219	Intermediate Similarity	NPC470842
0.8219	Intermediate Similarity	NPC244923
0.8214	Intermediate Similarity	NPC31799
0.8214	Intermediate Similarity	NPC117609
0.8214	Intermediate Similarity	NPC27659
0.8212	Intermediate Similarity	NPC315520
0.8207	Intermediate Similarity	NPC138099
0.8207	Intermediate Similarity	NPC242994
0.8207	Intermediate Similarity	NPC143438
0.8207	Intermediate Similarity	NPC1268
0.8205	Intermediate Similarity	NPC316457
0.8201	Intermediate Similarity	NPC179898
0.8194	Intermediate Similarity	NPC471905
0.8194	Intermediate Similarity	NPC301341
0.8194	Intermediate Similarity	NPC147418
0.8194	Intermediate Similarity	NPC301915
0.8194	Intermediate Similarity	NPC471452
0.8194	Intermediate Similarity	NPC261292
0.8194	Intermediate Similarity	NPC284184
0.8188	Intermediate Similarity	NPC202112
0.8188	Intermediate Similarity	NPC147250
0.8188	Intermediate Similarity	NPC51513
0.8182	Intermediate Similarity	NPC283088
0.8182	Intermediate Similarity	NPC474861
0.8182	Intermediate Similarity	NPC142027
0.8182	Intermediate Similarity	NPC61153
0.8182	Intermediate Similarity	NPC70859
0.8182	Intermediate Similarity	NPC283590
0.8182	Intermediate Similarity	NPC161632
0.8182	Intermediate Similarity	NPC130899
0.8176	Intermediate Similarity	NPC84568
0.8176	Intermediate Similarity	NPC478203
0.8176	Intermediate Similarity	NPC475201
0.8176	Intermediate Similarity	NPC19896

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 NPC114620 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	954
0.2-0.3	1630
0.3-0.4	2813
0.4-0.5	2007
0.5-0.6	1002
0.6-0.7	377
0.7-0.8	55
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
0.8519	High Similarity	NPD1470	Approved
0.8252	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD1201	Approved
0.8045	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD3226	Approved
0.7724	Intermediate Similarity	NPD943	Approved
0.7651	Intermediate Similarity	NPD1471	Phase 3
0.7647	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1510	Phase 2
0.7632	Intermediate Similarity	NPD3300	Phase 2
0.7619	Intermediate Similarity	NPD1607	Approved
0.7603	Intermediate Similarity	NPD1240	Approved
0.76	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1549	Phase 2
0.7582	Intermediate Similarity	NPD7390	Discontinued
0.7558	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2346	Discontinued
0.7533	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2534	Approved
0.7532	Intermediate Similarity	NPD2533	Approved
0.7532	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD3882	Suspended
0.7484	Intermediate Similarity	NPD7819	Suspended
0.7484	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5405	Approved
0.7467	Intermediate Similarity	NPD5406	Approved
0.7467	Intermediate Similarity	NPD5404	Approved
0.7467	Intermediate Similarity	NPD5408	Approved
0.7466	Intermediate Similarity	NPD3764	Approved
0.7453	Intermediate Similarity	NPD7075	Discontinued
0.7427	Intermediate Similarity	NPD8150	Discontinued
0.7423	Intermediate Similarity	NPD6959	Discontinued
0.7421	Intermediate Similarity	NPD1934	Approved
0.7419	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD2344	Approved
0.741	Intermediate Similarity	NPD3751	Discontinued
0.741	Intermediate Similarity	NPD9545	Approved
0.7405	Intermediate Similarity	NPD4380	Phase 2
0.7378	Intermediate Similarity	NPD6232	Discontinued
0.7375	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1512	Approved
0.7351	Intermediate Similarity	NPD2935	Discontinued
0.7349	Intermediate Similarity	NPD7473	Discontinued
0.7296	Intermediate Similarity	NPD6599	Discontinued
0.7273	Intermediate Similarity	NPD6535	Approved
0.7273	Intermediate Similarity	NPD6534	Approved
0.7244	Intermediate Similarity	NPD6799	Approved
0.7244	Intermediate Similarity	NPD1511	Approved
0.7241	Intermediate Similarity	NPD1164	Approved
0.7237	Intermediate Similarity	NPD2796	Approved
0.7226	Intermediate Similarity	NPD6190	Approved
0.7226	Intermediate Similarity	NPD2309	Approved
0.7222	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6801	Discontinued
0.72	Intermediate Similarity	NPD230	Phase 1
0.7197	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6166	Phase 2
0.7186	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2799	Discontinued
0.7171	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6780	Approved
0.7167	Intermediate Similarity	NPD6777	Approved
0.7167	Intermediate Similarity	NPD6782	Approved
0.7167	Intermediate Similarity	NPD6776	Approved
0.7167	Intermediate Similarity	NPD6779	Approved
0.7167	Intermediate Similarity	NPD6778	Approved
0.7167	Intermediate Similarity	NPD6781	Approved
0.7161	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4628	Phase 3
0.716	Intermediate Similarity	NPD2801	Approved
0.7151	Intermediate Similarity	NPD7699	Phase 2
0.7151	Intermediate Similarity	NPD7700	Phase 2
0.7143	Intermediate Similarity	NPD7435	Discontinued
0.7143	Intermediate Similarity	NPD9493	Approved
0.7134	Intermediate Similarity	NPD3749	Approved
0.7124	Intermediate Similarity	NPD1551	Phase 2
0.7117	Intermediate Similarity	NPD5402	Approved
0.7117	Intermediate Similarity	NPD3817	Phase 2
0.7114	Intermediate Similarity	NPD2313	Discontinued
0.7113	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD8320	Phase 1
0.7104	Intermediate Similarity	NPD8319	Approved
0.7097	Intermediate Similarity	NPD2800	Approved
0.7083	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD3787	Discontinued
0.7065	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3019	Approved
0.7063	Intermediate Similarity	NPD2932	Approved
0.7059	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3750	Approved
0.7049	Intermediate Similarity	NPD7696	Phase 3
0.7049	Intermediate Similarity	NPD7698	Approved
0.7049	Intermediate Similarity	NPD7697	Approved
0.7048	Intermediate Similarity	NPD5494	Approved
0.7045	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7411	Suspended
0.703	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD8434	Phase 2
0.7015	Intermediate Similarity	NPD1237	Approved
0.7011	Intermediate Similarity	NPD7870	Phase 2
0.7011	Intermediate Similarity	NPD7871	Phase 2
0.7006	Intermediate Similarity	NPD1247	Approved
0.7	Intermediate Similarity	NPD3818	Discontinued
0.6994	Remote Similarity	NPD4955	Approved
0.6994	Remote Similarity	NPD5034	Approved
0.6994	Remote Similarity	NPD5028	Approved
0.6994	Remote Similarity	NPD36	Approved
0.6994	Remote Similarity	NPD4954	Approved
0.6994	Remote Similarity	NPD5026	Approved
0.6985	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6797	Phase 2
0.6964	Remote Similarity	NPD5710	Approved
0.6964	Remote Similarity	NPD5711	Approved
0.6962	Remote Similarity	NPD7236	Approved
0.6959	Remote Similarity	NPD5844	Phase 1
0.6959	Remote Similarity	NPD2798	Approved
0.6954	Remote Similarity	NPD8312	Approved
0.6954	Remote Similarity	NPD6663	Approved
0.6954	Remote Similarity	NPD8313	Approved
0.6936	Remote Similarity	NPD5030	Phase 2
0.6936	Remote Similarity	NPD7251	Discontinued
0.6934	Remote Similarity	NPD74	Approved
0.6934	Remote Similarity	NPD9266	Approved
0.6932	Remote Similarity	NPD5038	Approved
0.6932	Remote Similarity	NPD5037	Approved
0.6918	Remote Similarity	NPD1608	Approved
0.6915	Remote Similarity	NPD7874	Approved
0.6915	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD5736	Approved
0.6906	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6100	Approved
0.6903	Remote Similarity	NPD6099	Approved
0.6898	Remote Similarity	NPD7701	Phase 2
0.6897	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7808	Phase 3
0.6894	Remote Similarity	NPD920	Approved
0.6894	Remote Similarity	NPD5403	Approved
0.6892	Remote Similarity	NPD1203	Approved
0.6886	Remote Similarity	NPD919	Approved
0.6882	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5036	Approved
0.6875	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5401	Approved
0.6867	Remote Similarity	NPD7768	Phase 2
0.6867	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD447	Suspended
0.6861	Remote Similarity	NPD9267	Approved
0.6861	Remote Similarity	NPD9263	Approved
0.6861	Remote Similarity	NPD9264	Approved
0.6859	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5760	Phase 2
0.6848	Remote Similarity	NPD5761	Phase 2
0.6839	Remote Similarity	NPD6559	Discontinued
0.6839	Remote Similarity	NPD5031	Approved
0.6839	Remote Similarity	NPD5027	Approved
0.6839	Remote Similarity	NPD5029	Approved
0.6835	Remote Similarity	NPD8166	Discontinued
0.6833	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6213	Phase 3
0.6833	Remote Similarity	NPD6212	Phase 3
0.6824	Remote Similarity	NPD3926	Phase 2
0.6824	Remote Similarity	NPD1283	Approved
0.6824	Remote Similarity	NPD1876	Approved
0.6821	Remote Similarity	NPD7074	Phase 3
0.681	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD9717	Approved
0.6803	Remote Similarity	NPD3972	Approved
0.6803	Remote Similarity	NPD9269	Phase 2
0.68	Remote Similarity	NPD9494	Approved
0.6797	Remote Similarity	NPD4060	Phase 1
0.6789	Remote Similarity	NPD7801	Approved
0.6782	Remote Similarity	NPD5953	Discontinued
0.6776	Remote Similarity	NPD411	Approved
0.677	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7054	Approved
0.6761	Remote Similarity	NPD5035	Approved
0.6759	Remote Similarity	NPD9268	Approved
0.6759	Remote Similarity	NPD1651	Approved
0.6753	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7239	Suspended
0.6747	Remote Similarity	NPD1465	Phase 2
0.6733	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD520	Approved
0.6731	Remote Similarity	NPD3748	Approved
0.6731	Remote Similarity	NPD7033	Discontinued
0.673	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7003	Approved
0.6728	Remote Similarity	NPD6273	Approved
0.6724	Remote Similarity	NPD7472	Approved
0.6712	Remote Similarity	NPD17	Approved
0.671	Remote Similarity	NPD6651	Approved
0.6707	Remote Similarity	NPD2296	Approved
0.6707	Remote Similarity	NPD7458	Discontinued
0.6705	Remote Similarity	NPD7177	Discontinued
0.6705	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6844	Discontinued

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