NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.06
Volume:	261.953
LogP:	1.506
LogD:	1.833
LogS:	-2.563
# Rotatable Bonds:	2
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.763
Synthetic Accessibility Score:	3.643
Fsp3:	0.214
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:	-5.447
MDCK Permeability:	9.5699851954123e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.041
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.725
30% Bioavailability (F30%):	0.467

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	95.679931640625%
Volume Distribution (VD):	0.706
Pgp-substrate:	4.801004409790039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.554
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.158
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.469
CYP2C9-substrate:	0.844
CYP2D6-inhibitor:	0.311
CYP2D6-substrate:	0.635
CYP3A4-inhibitor:	0.319
CYP3A4-substrate:	0.196

ADMET: Excretion

Clearance (CL):	12.347
Half-life (T1/2):	0.855

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.155
Drug-inuced Liver Injury (DILI):	0.406
AMES Toxicity:	0.116
Rat Oral Acute Toxicity:	0.276
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.221
Carcinogencity:	0.793
Eye Corrosion:	0.003
Eye Irritation:	0.042
Respiratory Toxicity:	0.046

Download Data

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

Natural Product: NPC116822

Natural Product ID:	NPC116822
*Common Name:**	Caesalpiniaphenol B
IUPAC Name:	(3R)-3,7-dihydroxy-3-[(5-oxo-2H-furan-4-yl)methyl]-2H-chromen-4-one
Synonyms:	Caesalpiniaphenol B
Standard InCHIKey:	KCUVXAULFNGKQN-CQSZACIVSA-N
Standard InCHI:	InChI=1S/C14H12O6/c15-9-1-2-10-11(5-9)20-7-14(18,12(10)16)6-8-3-4-19-13(8)17/h1-3,5,15,18H,4,6-7H2/t14-/m1/s1
SMILES:	Oc1ccc2c(c1)OC[C@](C2=O)(O)CC1=CCOC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2208388
PubChem CID:	71457914
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[19420770]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23127886]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23234407]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	seeds	Nanning, Guangxi Province, China	2013-APR	PMID[26398312]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[514044]
NPT35	Others	n.a.		IC50	=	95620.0	nM	PMID[514044]

☑ 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 NPC116822 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	362
0.1-0.2	1554
0.2-0.3	4269
0.3-0.4	9095
0.4-0.5	8926
0.5-0.6	4058
0.6-0.7	5955
0.7-0.8	5447
0.8-0.85	2631
0.85-0.9	391
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9184	High Similarity	NPC229190
0.9172	High Similarity	NPC150023
0.9116	High Similarity	NPC316535
0.9067	High Similarity	NPC267117
0.9054	High Similarity	NPC148011
0.9054	High Similarity	NPC1940
0.9007	High Similarity	NPC471229
0.9	High Similarity	NPC477941
0.9	High Similarity	NPC277032
0.8993	High Similarity	NPC472918
0.8986	High Similarity	NPC279417
0.8986	High Similarity	NPC49130
0.8986	High Similarity	NPC142731
0.8986	High Similarity	NPC306607
0.8986	High Similarity	NPC62290
0.8986	High Similarity	NPC4152
0.8986	High Similarity	NPC326506
0.8986	High Similarity	NPC208176
0.8889	High Similarity	NPC203080
0.8889	High Similarity	NPC301233
0.8882	High Similarity	NPC295650
0.8867	High Similarity	NPC40086
0.8867	High Similarity	NPC476182
0.8867	High Similarity	NPC44721
0.8867	High Similarity	NPC122828
0.8867	High Similarity	NPC176869
0.8867	High Similarity	NPC3779
0.8867	High Similarity	NPC211466
0.8839	High Similarity	NPC476930
0.8824	High Similarity	NPC256141
0.8824	High Similarity	NPC210597
0.8816	High Similarity	NPC180351
0.8808	High Similarity	NPC211811
0.8808	High Similarity	NPC218569
0.8797	High Similarity	NPC472581
0.8774	High Similarity	NPC474638
0.8767	High Similarity	NPC287068
0.8767	High Similarity	NPC160972
0.8766	High Similarity	NPC141212
0.8766	High Similarity	NPC100134
0.8766	High Similarity	NPC209760
0.8742	High Similarity	NPC21835
0.8742	High Similarity	NPC129650
0.8734	High Similarity	NPC219861
0.8725	High Similarity	NPC162476
0.8725	High Similarity	NPC471520
0.8716	High Similarity	NPC16455
0.8716	High Similarity	NPC307990
0.871	High Similarity	NPC476169
0.871	High Similarity	NPC473241
0.871	High Similarity	NPC471116
0.8707	High Similarity	NPC329225
0.8707	High Similarity	NPC472460
0.8707	High Similarity	NPC147686
0.8701	High Similarity	NPC473996
0.8701	High Similarity	NPC243171
0.8701	High Similarity	NPC171651
0.8701	High Similarity	NPC35567
0.8693	High Similarity	NPC472421
0.8667	High Similarity	NPC242100
0.8667	High Similarity	NPC470216
0.8667	High Similarity	NPC255133
0.8662	High Similarity	NPC55738
0.8658	High Similarity	NPC310128
0.8654	High Similarity	NPC313922
0.8649	High Similarity	NPC471697
0.8649	High Similarity	NPC261234
0.8645	High Similarity	NPC246328
0.8645	High Similarity	NPC325028
0.8645	High Similarity	NPC256346
0.8645	High Similarity	NPC27532
0.8645	High Similarity	NPC293286
0.8645	High Similarity	NPC192189
0.8639	High Similarity	NPC295261
0.8639	High Similarity	NPC243083
0.8639	High Similarity	NPC290291
0.8639	High Similarity	NPC84585
0.8639	High Similarity	NPC287246
0.8639	High Similarity	NPC254841
0.8639	High Similarity	NPC107586
0.8639	High Similarity	NPC32441
0.8639	High Similarity	NPC79943
0.8639	High Similarity	NPC476480
0.8639	High Similarity	NPC299379
0.8639	High Similarity	NPC275055
0.8639	High Similarity	NPC13768
0.8639	High Similarity	NPC296490
0.8639	High Similarity	NPC12296
0.8636	High Similarity	NPC474744
0.8636	High Similarity	NPC262039
0.8636	High Similarity	NPC472636
0.8636	High Similarity	NPC472580
0.8636	High Similarity	NPC319910
0.8636	High Similarity	NPC278476
0.8636	High Similarity	NPC263384
0.8636	High Similarity	NPC472423
0.8636	High Similarity	NPC471676
0.8636	High Similarity	NPC472420
0.8636	High Similarity	NPC474772
0.8636	High Similarity	NPC254412
0.8636	High Similarity	NPC244577
0.8636	High Similarity	NPC262038
0.8636	High Similarity	NPC472422
0.863	High Similarity	NPC9985
0.863	High Similarity	NPC239495
0.8618	High Similarity	NPC202494
0.8618	High Similarity	NPC91902
0.8618	High Similarity	NPC470670
0.8618	High Similarity	NPC473133
0.8618	High Similarity	NPC85773
0.8618	High Similarity	NPC47388
0.8611	High Similarity	NPC65060
0.8609	High Similarity	NPC303185
0.8609	High Similarity	NPC470857
0.8609	High Similarity	NPC184649
0.8609	High Similarity	NPC297788
0.8609	High Similarity	NPC71210
0.8608	High Similarity	NPC471744
0.8608	High Similarity	NPC306978
0.8599	High Similarity	NPC67876
0.8599	High Similarity	NPC6985
0.8599	High Similarity	NPC43638
0.8591	High Similarity	NPC269652
0.8591	High Similarity	NPC307287
0.8591	High Similarity	NPC281207
0.859	High Similarity	NPC48579
0.859	High Similarity	NPC108937
0.859	High Similarity	NPC217706
0.859	High Similarity	NPC304207
0.859	High Similarity	NPC237560
0.859	High Similarity	NPC279218
0.859	High Similarity	NPC259710
0.859	High Similarity	NPC207809
0.8581	High Similarity	NPC124269
0.8581	High Similarity	NPC260491
0.8581	High Similarity	NPC188947
0.8581	High Similarity	NPC246162
0.8581	High Similarity	NPC275878
0.8581	High Similarity	NPC216035
0.8581	High Similarity	NPC9743
0.8581	High Similarity	NPC99333
0.8581	High Similarity	NPC327269
0.8581	High Similarity	NPC138288
0.8581	High Similarity	NPC476238
0.8581	High Similarity	NPC240476
0.8581	High Similarity	NPC36835
0.8581	High Similarity	NPC61506
0.8581	High Similarity	NPC31627
0.8581	High Similarity	NPC280284
0.8581	High Similarity	NPC477957
0.8581	High Similarity	NPC118813
0.8581	High Similarity	NPC217149
0.8571	High Similarity	NPC240147
0.8571	High Similarity	NPC256042
0.8571	High Similarity	NPC121243
0.8571	High Similarity	NPC116775
0.8571	High Similarity	NPC475717
0.8571	High Similarity	NPC187432
0.8571	High Similarity	NPC281917
0.8571	High Similarity	NPC216361
0.8571	High Similarity	NPC470107
0.8571	High Similarity	NPC187826
0.8571	High Similarity	NPC105136
0.8562	High Similarity	NPC121703
0.8553	High Similarity	NPC282169
0.8553	High Similarity	NPC299011
0.8553	High Similarity	NPC260946
0.8553	High Similarity	NPC92589
0.8553	High Similarity	NPC112418
0.8544	High Similarity	NPC152904
0.8543	High Similarity	NPC113770
0.8535	High Similarity	NPC201837
0.8535	High Similarity	NPC146636
0.8535	High Similarity	NPC265480
0.8535	High Similarity	NPC149368
0.8535	High Similarity	NPC129053
0.8535	High Similarity	NPC19860
0.8535	High Similarity	NPC78554
0.8535	High Similarity	NPC469936
0.8535	High Similarity	NPC109967
0.8535	High Similarity	NPC321372
0.8535	High Similarity	NPC20530
0.8535	High Similarity	NPC474609
0.8535	High Similarity	NPC474738
0.8535	High Similarity	NPC215917
0.8535	High Similarity	NPC475797
0.8535	High Similarity	NPC10754
0.8535	High Similarity	NPC127406
0.8533	High Similarity	NPC3188
0.8533	High Similarity	NPC136840
0.8533	High Similarity	NPC171870
0.8526	High Similarity	NPC469405
0.8526	High Similarity	NPC236756
0.8526	High Similarity	NPC7989
0.8526	High Similarity	NPC311579
0.8526	High Similarity	NPC268193
0.8526	High Similarity	NPC180301
0.8526	High Similarity	NPC472583
0.8526	High Similarity	NPC223701
0.8526	High Similarity	NPC248793

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 NPC116822 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	911
0.2-0.3	1892
0.3-0.4	2579
0.4-0.5	1829
0.5-0.6	1043
0.6-0.7	394
0.7-0.8	130
0.8-0.85	41
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8792	High Similarity	NPD6799	Approved
0.8718	High Similarity	NPD7075	Discontinued
0.8707	High Similarity	NPD1549	Phase 2
0.8645	High Similarity	NPD7096	Clinical (unspecified phase)
0.8639	High Similarity	NPD1552	Clinical (unspecified phase)
0.8639	High Similarity	NPD1550	Clinical (unspecified phase)
0.8571	High Similarity	NPD6599	Discontinued
0.8516	High Similarity	NPD7411	Suspended
0.8462	Intermediate Similarity	NPD6801	Discontinued
0.8418	Intermediate Similarity	NPD3882	Suspended
0.8378	Intermediate Similarity	NPD1510	Phase 2
0.8366	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD1240	Approved
0.8344	Intermediate Similarity	NPD1934	Approved
0.8333	Intermediate Similarity	NPD4380	Phase 2
0.8312	Intermediate Similarity	NPD1512	Approved
0.8258	Intermediate Similarity	NPD5403	Approved
0.825	Intermediate Similarity	NPD3749	Approved
0.8247	Intermediate Similarity	NPD5401	Approved
0.8243	Intermediate Similarity	NPD1607	Approved
0.8239	Intermediate Similarity	NPD3817	Phase 2
0.82	Intermediate Similarity	NPD1551	Phase 2
0.8187	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1511	Approved
0.8176	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD920	Approved
0.8129	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD5402	Approved
0.8092	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD3818	Discontinued
0.8063	Intermediate Similarity	NPD2801	Approved
0.8063	Intermediate Similarity	NPD7819	Suspended
0.8061	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6166	Phase 2
0.8061	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD1247	Approved
0.7987	Intermediate Similarity	NPD3750	Approved
0.7987	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD919	Approved
0.7961	Intermediate Similarity	NPD2796	Approved
0.7929	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1243	Approved
0.7922	Intermediate Similarity	NPD2800	Approved
0.7898	Intermediate Similarity	NPD2532	Approved
0.7898	Intermediate Similarity	NPD2533	Approved
0.7898	Intermediate Similarity	NPD2534	Approved
0.7877	Intermediate Similarity	NPD1203	Approved
0.7852	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1465	Phase 2
0.7824	Intermediate Similarity	NPD6797	Phase 2
0.7815	Intermediate Similarity	NPD230	Phase 1
0.7793	Intermediate Similarity	NPD9717	Approved
0.7778	Intermediate Similarity	NPD7251	Discontinued
0.7778	Intermediate Similarity	NPD6559	Discontinued
0.7765	Intermediate Similarity	NPD7074	Phase 3
0.7756	Intermediate Similarity	NPD4628	Phase 3
0.7744	Intermediate Similarity	NPD7768	Phase 2
0.7733	Intermediate Similarity	NPD7808	Phase 3
0.7711	Intermediate Similarity	NPD5494	Approved
0.7706	Intermediate Similarity	NPD7054	Approved
0.7706	Intermediate Similarity	NPD7286	Phase 2
0.7697	Intermediate Similarity	NPD447	Suspended
0.7662	Intermediate Similarity	NPD3748	Approved
0.7661	Intermediate Similarity	NPD7472	Approved
0.7632	Intermediate Similarity	NPD943	Approved
0.7619	Intermediate Similarity	NPD6232	Discontinued
0.7616	Intermediate Similarity	NPD2313	Discontinued
0.7616	Intermediate Similarity	NPD5953	Discontinued
0.7613	Intermediate Similarity	NPD2935	Discontinued
0.7603	Intermediate Similarity	NPD422	Phase 1
0.7593	Intermediate Similarity	NPD3226	Approved
0.7588	Intermediate Similarity	NPD7473	Discontinued
0.7569	Intermediate Similarity	NPD9545	Approved
0.7564	Intermediate Similarity	NPD2344	Approved
0.7548	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2799	Discontinued
0.7544	Intermediate Similarity	NPD3751	Discontinued
0.7529	Intermediate Similarity	NPD2403	Approved
0.75	Intermediate Similarity	NPD5844	Phase 1
0.7486	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2354	Approved
0.7483	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6832	Phase 2
0.7471	Intermediate Similarity	NPD3926	Phase 2
0.7467	Intermediate Similarity	NPD1019	Discontinued
0.7458	Intermediate Similarity	NPD8434	Phase 2
0.7456	Intermediate Similarity	NPD6959	Discontinued
0.7436	Intermediate Similarity	NPD7033	Discontinued
0.7431	Intermediate Similarity	NPD9493	Approved
0.7421	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6651	Approved
0.7418	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD5711	Approved
0.7412	Intermediate Similarity	NPD5710	Approved
0.7386	Intermediate Similarity	NPD6798	Discontinued
0.7386	Intermediate Similarity	NPD3268	Approved
0.7386	Intermediate Similarity	NPD1296	Phase 2
0.7375	Intermediate Similarity	NPD2309	Approved
0.7358	Intermediate Similarity	NPD1652	Phase 2
0.7355	Intermediate Similarity	NPD1933	Approved
0.7355	Intermediate Similarity	NPD6355	Discontinued
0.7342	Intermediate Similarity	NPD2346	Discontinued
0.731	Intermediate Similarity	NPD3787	Discontinued
0.729	Intermediate Similarity	NPD1613	Approved
0.729	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4287	Approved
0.7273	Intermediate Similarity	NPD411	Approved
0.7273	Intermediate Similarity	NPD3764	Approved
0.7267	Intermediate Similarity	NPD3887	Approved
0.7267	Intermediate Similarity	NPD6190	Approved
0.7256	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1610	Phase 2
0.7244	Intermediate Similarity	NPD5124	Phase 1
0.7244	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2353	Approved
0.7233	Intermediate Similarity	NPD1471	Phase 3
0.7226	Intermediate Similarity	NPD6233	Phase 2
0.7219	Intermediate Similarity	NPD3225	Approved
0.7215	Intermediate Similarity	NPD4308	Phase 3
0.7212	Intermediate Similarity	NPD1653	Approved
0.7211	Intermediate Similarity	NPD1548	Phase 1
0.7207	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD9269	Phase 2
0.7195	Intermediate Similarity	NPD5049	Phase 3
0.7191	Intermediate Similarity	NPD8312	Approved
0.7191	Intermediate Similarity	NPD8313	Approved
0.719	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2424	Discontinued
0.7186	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3266	Approved
0.7171	Intermediate Similarity	NPD3267	Approved
0.717	Intermediate Similarity	NPD6100	Approved
0.717	Intermediate Similarity	NPD6099	Approved
0.7168	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2654	Approved
0.7135	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1241	Discontinued
0.709	Intermediate Similarity	NPD7435	Discontinued
0.7086	Intermediate Similarity	NPD1608	Approved
0.7086	Intermediate Similarity	NPD1481	Phase 2
0.7078	Intermediate Similarity	NPD9494	Approved
0.7073	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8150	Discontinued
0.7062	Intermediate Similarity	NPD1729	Discontinued
0.7059	Intermediate Similarity	NPD2797	Approved
0.7059	Intermediate Similarity	NPD4288	Approved
0.7055	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7199	Phase 2
0.7047	Intermediate Similarity	NPD9268	Approved
0.7045	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4908	Phase 1
0.7021	Intermediate Similarity	NPD6782	Approved
0.7021	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6781	Approved
0.7021	Intermediate Similarity	NPD6780	Approved
0.7021	Intermediate Similarity	NPD6778	Approved
0.7021	Intermediate Similarity	NPD6777	Approved
0.7021	Intermediate Similarity	NPD6779	Approved
0.7021	Intermediate Similarity	NPD6776	Approved
0.702	Intermediate Similarity	NPD1091	Approved
0.702	Intermediate Similarity	NPD1535	Discovery
0.7013	Intermediate Similarity	NPD5647	Approved
0.7011	Intermediate Similarity	NPD6808	Phase 2
0.7006	Intermediate Similarity	NPD4062	Phase 3
0.6993	Remote Similarity	NPD74	Approved
0.6993	Remote Similarity	NPD9266	Approved
0.6983	Remote Similarity	NPD6104	Discontinued
0.6982	Remote Similarity	NPD5890	Approved
0.6982	Remote Similarity	NPD5889	Approved
0.6979	Remote Similarity	NPD7584	Approved
0.6964	Remote Similarity	NPD7458	Discontinued
0.6962	Remote Similarity	NPD4307	Phase 2
0.6962	Remote Similarity	NPD4060	Phase 1
0.6959	Remote Similarity	NPD5353	Approved
0.6948	Remote Similarity	NPD1164	Approved
0.6943	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6234	Discontinued
0.6923	Remote Similarity	NPD9263	Approved
0.6923	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6585	Discontinued
0.6923	Remote Similarity	NPD9264	Approved
0.6923	Remote Similarity	NPD9267	Approved
0.6918	Remote Similarity	NPD4340	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