NPASS Compound

Structure

CID105512 OpenBabel06191715452D 21 23 0 0 1 0 0 0 0 0999 V2000 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 9 1 0 0 0 0 2 3 2 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 9 1 0 0 0 0 6 9 2 0 0 0 0 6 14 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 21 1 0 0 0 0 10 5 1 6 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 14 2 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.08
Volume:	285.119
LogP:	2.412
LogD:	2.562
LogS:	-3.693
# Rotatable Bonds:	2
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.737
Synthetic Accessibility Score:	2.899
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.73
MDCK Permeability:	1.0438901881570928e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.959
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	96.9314193725586%
Volume Distribution (VD):	0.52
Pgp-substrate:	2.4075026512145996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.936
CYP1A2-substrate:	0.39
CYP2C19-inhibitor:	0.723
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.738
CYP2C9-substrate:	0.878
CYP2D6-inhibitor:	0.812
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.723
CYP3A4-substrate:	0.231

ADMET: Excretion

Clearance (CL):	17.979
Half-life (T1/2):	0.861

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.172
Drug-inuced Liver Injury (DILI):	0.462
AMES Toxicity:	0.709
Rat Oral Acute Toxicity:	0.204
Maximum Recommended Daily Dose:	0.213
Skin Sensitization:	0.934
Carcinogencity:	0.808
Eye Corrosion:	0.003
Eye Irritation:	0.922
Respiratory Toxicity:	0.039

Download Data

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

Natural Product: NPC105512

Natural Product ID:	NPC105512
*Common Name:**	3-Deoxysappanone B
IUPAC Name:	(3S)-3-[(3,4-dihydroxyphenyl)methyl]-7-hydroxy-2,3-dihydrochromen-4-one
Synonyms:	3-Deoxysappanone B
Standard InCHIKey:	KCUXSQJYIWEGRG-JTQLQIEISA-N
Standard InCHI:	InChI=1S/C16H14O5/c17-11-2-3-12-15(7-11)21-8-10(16(12)20)5-9-1-4-13(18)14(19)6-9/h1-4,6-7,10,17-19H,5,8H2/t10-/m0/s1
SMILES:	Oc1ccc2c(c1)OC[C@@H](C2=O)Cc1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1916186
PubChem CID:	57396358
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002507] Homoisoflavonoids [CHEMONTID:0002508] Homoisoflavans [CHEMONTID:0002898] Homoisoflavanones

*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]
NPO2554	Biancaea sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2554	Biancaea sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2554	Biancaea sappan	Species	Fabaceae	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	2
Others	1

Activity Type	# Activity
Cell Line	1
Organism	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	=	42400.0	nM	PMID[552957]
NPT1339	Organism	Arabidopsis thaliana	Arabidopsis thaliana	MAC	=	2.7	uM	PMID[552956]
NPT35	Others	n.a.		IC50	=	65340.0	nM	PMID[552957]

☑ 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 NPC105512 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	414
0.1-0.2	1690
0.2-0.3	4381
0.3-0.4	10734
0.4-0.5	7030
0.5-0.6	3385
0.6-0.7	4855
0.7-0.8	5624
0.8-0.85	2496
0.85-0.9	1694
0.9-0.95	366
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC3036
0.9859	High Similarity	NPC95864
0.9726	High Similarity	NPC469550
0.9722	High Similarity	NPC183959
0.9722	High Similarity	NPC1612
0.9658	High Similarity	NPC260979
0.9658	High Similarity	NPC472912
0.9653	High Similarity	NPC294852
0.9653	High Similarity	NPC321011
0.9653	High Similarity	NPC188679
0.9592	High Similarity	NPC141212
0.9589	High Similarity	NPC31363
0.953	High Similarity	NPC129684
0.953	High Similarity	NPC299520
0.9524	High Similarity	NPC302950
0.9524	High Similarity	NPC219582
0.9524	High Similarity	NPC257648
0.9524	High Similarity	NPC236637
0.9524	High Similarity	NPC477231
0.9521	High Similarity	NPC29231
0.9517	High Similarity	NPC196277
0.9517	High Similarity	NPC272721
0.9517	High Similarity	NPC119059
0.9517	High Similarity	NPC43669
0.951	High Similarity	NPC38065
0.951	High Similarity	NPC242893
0.9463	High Similarity	NPC474638
0.9459	High Similarity	NPC192083
0.9459	High Similarity	NPC325028
0.9459	High Similarity	NPC27532
0.9459	High Similarity	NPC213896
0.9459	High Similarity	NPC246328
0.9459	High Similarity	NPC256346
0.9459	High Similarity	NPC18727
0.9456	High Similarity	NPC204515
0.9448	High Similarity	NPC77378
0.9448	High Similarity	NPC108406
0.9444	High Similarity	NPC70136
0.94	High Similarity	NPC472911
0.94	High Similarity	NPC245758
0.94	High Similarity	NPC291508
0.94	High Similarity	NPC210084
0.94	High Similarity	NPC99597
0.94	High Similarity	NPC52530
0.94	High Similarity	NPC472914
0.94	High Similarity	NPC472910
0.94	High Similarity	NPC472913
0.94	High Similarity	NPC67876
0.94	High Similarity	NPC222814
0.94	High Similarity	NPC96167
0.9396	High Similarity	NPC255807
0.9396	High Similarity	NPC31018
0.9396	High Similarity	NPC168247
0.9396	High Similarity	NPC321779
0.9396	High Similarity	NPC152951
0.9396	High Similarity	NPC117992
0.9396	High Similarity	NPC67396
0.9396	High Similarity	NPC57674
0.9396	High Similarity	NPC2928
0.9396	High Similarity	NPC230149
0.9392	High Similarity	NPC61506
0.9392	High Similarity	NPC240476
0.9392	High Similarity	NPC36835
0.9392	High Similarity	NPC246162
0.9392	High Similarity	NPC9743
0.9392	High Similarity	NPC260491
0.9392	High Similarity	NPC106976
0.9388	High Similarity	NPC62042
0.9384	High Similarity	NPC80710
0.9384	High Similarity	NPC254702
0.9384	High Similarity	NPC194856
0.9384	High Similarity	NPC203747
0.9384	High Similarity	NPC194653
0.9384	High Similarity	NPC139364
0.9384	High Similarity	NPC276930
0.9375	High Similarity	NPC279121
0.9371	High Similarity	NPC301178
0.9371	High Similarity	NPC284556
0.9366	High Similarity	NPC261234
0.9338	High Similarity	NPC55738
0.9333	High Similarity	NPC35038
0.9333	High Similarity	NPC472916
0.9333	High Similarity	NPC278778
0.9333	High Similarity	NPC291878
0.9333	High Similarity	NPC326037
0.9333	High Similarity	NPC255106
0.9333	High Similarity	NPC282307
0.9333	High Similarity	NPC471500
0.9333	High Similarity	NPC320825
0.9333	High Similarity	NPC235165
0.9333	High Similarity	NPC170026
0.9333	High Similarity	NPC195796
0.9333	High Similarity	NPC24640
0.9333	High Similarity	NPC13858
0.9329	High Similarity	NPC206238
0.9329	High Similarity	NPC273462
0.9329	High Similarity	NPC292214
0.9329	High Similarity	NPC74924
0.9329	High Similarity	NPC33051
0.9329	High Similarity	NPC271779
0.9329	High Similarity	NPC167091
0.9329	High Similarity	NPC227337
0.9329	High Similarity	NPC49402
0.9329	High Similarity	NPC70433
0.9329	High Similarity	NPC88645
0.9329	High Similarity	NPC298692
0.9324	High Similarity	NPC154345
0.9324	High Similarity	NPC260895
0.9324	High Similarity	NPC251110
0.932	High Similarity	NPC333691
0.932	High Similarity	NPC52005
0.932	High Similarity	NPC38545
0.932	High Similarity	NPC195763
0.932	High Similarity	NPC142876
0.932	High Similarity	NPC137062
0.932	High Similarity	NPC264550
0.932	High Similarity	NPC87125
0.932	High Similarity	NPC171916
0.932	High Similarity	NPC287101
0.932	High Similarity	NPC223579
0.932	High Similarity	NPC270465
0.932	High Similarity	NPC40290
0.932	High Similarity	NPC139293
0.932	High Similarity	NPC200060
0.932	High Similarity	NPC69430
0.932	High Similarity	NPC264289
0.932	High Similarity	NPC183950
0.9315	High Similarity	NPC188074
0.9315	High Similarity	NPC51443
0.9315	High Similarity	NPC125449
0.9315	High Similarity	NPC168803
0.9315	High Similarity	NPC74881
0.9315	High Similarity	NPC207729
0.9306	High Similarity	NPC287722
0.9306	High Similarity	NPC202981
0.9306	High Similarity	NPC175013
0.9306	High Similarity	NPC471417
0.9296	High Similarity	NPC118813
0.9276	High Similarity	NPC474960
0.9272	High Similarity	NPC472963
0.9272	High Similarity	NPC475267
0.9272	High Similarity	NPC474836
0.9272	High Similarity	NPC27337
0.9272	High Similarity	NPC48208
0.9272	High Similarity	NPC181960
0.9272	High Similarity	NPC471515
0.9272	High Similarity	NPC469584
0.9272	High Similarity	NPC162869
0.9272	High Similarity	NPC474208
0.9272	High Similarity	NPC156057
0.9272	High Similarity	NPC471209
0.9272	High Similarity	NPC52889
0.9272	High Similarity	NPC474055
0.9272	High Similarity	NPC471479
0.9272	High Similarity	NPC472598
0.9267	High Similarity	NPC470327
0.9267	High Similarity	NPC234255
0.9267	High Similarity	NPC472909
0.9267	High Similarity	NPC477503
0.9267	High Similarity	NPC45849
0.9267	High Similarity	NPC200761
0.9267	High Similarity	NPC256925
0.9267	High Similarity	NPC113906
0.9262	High Similarity	NPC39007
0.9262	High Similarity	NPC161277
0.9262	High Similarity	NPC39732
0.9262	High Similarity	NPC19721
0.9262	High Similarity	NPC180234
0.9262	High Similarity	NPC60972
0.9262	High Similarity	NPC199100
0.9262	High Similarity	NPC120537
0.9262	High Similarity	NPC55205
0.9262	High Similarity	NPC101996
0.9257	High Similarity	NPC149127
0.9257	High Similarity	NPC61620
0.9257	High Similarity	NPC10467
0.9257	High Similarity	NPC338131
0.9257	High Similarity	NPC85131
0.9257	High Similarity	NPC184136
0.9257	High Similarity	NPC3825
0.9257	High Similarity	NPC286342
0.9257	High Similarity	NPC248102
0.9257	High Similarity	NPC188871
0.9257	High Similarity	NPC88804
0.9252	High Similarity	NPC118726
0.9252	High Similarity	NPC120464
0.9252	High Similarity	NPC218490
0.9252	High Similarity	NPC203077
0.9252	High Similarity	NPC166036
0.9252	High Similarity	NPC238279
0.9252	High Similarity	NPC12367
0.9247	High Similarity	NPC12377
0.9247	High Similarity	NPC209278
0.9247	High Similarity	NPC20791
0.9247	High Similarity	NPC179271
0.9241	High Similarity	NPC59551
0.9231	High Similarity	NPC316480
0.9225	High Similarity	NPC290291
0.9225	High Similarity	NPC275055
0.9216	High Similarity	NPC266314

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 NPC105512 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	963
0.2-0.3	1686
0.3-0.4	2616
0.4-0.5	1754
0.5-0.6	1070
0.6-0.7	483
0.7-0.8	135
0.8-0.85	34
0.85-0.9	16
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9524	High Similarity	NPD1934	Approved
0.9459	High Similarity	NPD2393	Clinical (unspecified phase)
0.9375	High Similarity	NPD1511	Approved
0.9247	High Similarity	NPD1512	Approved
0.9161	High Similarity	NPD1549	Phase 2
0.9091	High Similarity	NPD1552	Clinical (unspecified phase)
0.9091	High Similarity	NPD1550	Clinical (unspecified phase)
0.9079	High Similarity	NPD3882	Suspended
0.9073	High Similarity	NPD2801	Approved
0.8951	High Similarity	NPD1510	Phase 2
0.8917	High Similarity	NPD6167	Clinical (unspecified phase)
0.8917	High Similarity	NPD6168	Clinical (unspecified phase)
0.8917	High Similarity	NPD6166	Phase 2
0.8831	High Similarity	NPD4868	Clinical (unspecified phase)
0.8805	High Similarity	NPD3818	Discontinued
0.875	High Similarity	NPD4380	Phase 2
0.8696	High Similarity	NPD7074	Phase 3
0.8671	High Similarity	NPD943	Approved
0.8671	High Similarity	NPD1240	Approved
0.8667	High Similarity	NPD4378	Clinical (unspecified phase)
0.8654	High Similarity	NPD4381	Clinical (unspecified phase)
0.8654	High Similarity	NPD7075	Discontinued
0.8645	High Similarity	NPD3817	Phase 2
0.8634	High Similarity	NPD7054	Approved
0.863	High Similarity	NPD2796	Approved
0.8581	High Similarity	NPD7096	Clinical (unspecified phase)
0.8581	High Similarity	NPD7819	Suspended
0.858	High Similarity	NPD7472	Approved
0.8552	High Similarity	NPD1607	Approved
0.8544	High Similarity	NPD5494	Approved
0.8528	High Similarity	NPD6797	Phase 2
0.8526	High Similarity	NPD8443	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD6799	Approved
0.8476	Intermediate Similarity	NPD7251	Discontinued
0.8452	Intermediate Similarity	NPD7411	Suspended
0.8424	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1465	Phase 2
0.8313	Intermediate Similarity	NPD7808	Phase 3
0.8303	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD1613	Approved
0.8288	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD6801	Discontinued
0.8278	Intermediate Similarity	NPD3750	Approved
0.8269	Intermediate Similarity	NPD6599	Discontinued
0.8267	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD1551	Phase 2
0.8194	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD3749	Approved
0.8171	Intermediate Similarity	NPD7473	Discontinued
0.8148	Intermediate Similarity	NPD6959	Discontinued
0.811	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD230	Phase 1
0.8098	Intermediate Similarity	NPD6232	Discontinued
0.8077	Intermediate Similarity	NPD5403	Approved
0.8072	Intermediate Similarity	NPD5844	Phase 1
0.8072	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD5401	Approved
0.8063	Intermediate Similarity	NPD5402	Approved
0.8036	Intermediate Similarity	NPD6559	Discontinued
0.8025	Intermediate Similarity	NPD919	Approved
0.8012	Intermediate Similarity	NPD7768	Phase 2
0.7974	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD3748	Approved
0.7947	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD3926	Phase 2
0.7927	Intermediate Similarity	NPD1247	Approved
0.7905	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD1610	Phase 2
0.7902	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD2935	Discontinued
0.7895	Intermediate Similarity	NPD6100	Approved
0.7895	Intermediate Similarity	NPD6099	Approved
0.7857	Intermediate Similarity	NPD2800	Approved
0.7848	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD2344	Approved
0.7821	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD1203	Approved
0.7806	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD4628	Phase 3
0.777	Intermediate Similarity	NPD4908	Phase 1
0.7748	Intermediate Similarity	NPD1933	Approved
0.7748	Intermediate Similarity	NPD447	Suspended
0.7742	Intermediate Similarity	NPD1243	Approved
0.7736	Intermediate Similarity	NPD920	Approved
0.7722	Intermediate Similarity	NPD2534	Approved
0.7722	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD2532	Approved
0.7722	Intermediate Similarity	NPD2533	Approved
0.7718	Intermediate Similarity	NPD3027	Phase 3
0.7712	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2799	Discontinued
0.7711	Intermediate Similarity	NPD7199	Phase 2
0.7703	Intermediate Similarity	NPD9494	Approved
0.7697	Intermediate Similarity	NPD6651	Approved
0.7692	Intermediate Similarity	NPD3751	Discontinued
0.7692	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2313	Discontinued
0.7661	Intermediate Similarity	NPD5953	Discontinued
0.7643	Intermediate Similarity	NPD2309	Approved
0.764	Intermediate Similarity	NPD3226	Approved
0.7624	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1548	Phase 1
0.7619	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD2346	Discontinued
0.761	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1653	Approved
0.7551	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7286	Phase 2
0.7533	Intermediate Similarity	NPD6832	Phase 2
0.7532	Intermediate Similarity	NPD6190	Approved
0.7517	Intermediate Similarity	NPD2798	Approved
0.7516	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6234	Discontinued
0.7483	Intermediate Similarity	NPD9717	Approved
0.7483	Intermediate Similarity	NPD9269	Phase 2
0.7483	Intermediate Similarity	NPD1608	Approved
0.7456	Intermediate Similarity	NPD3787	Discontinued
0.7443	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD3268	Approved
0.7429	Intermediate Similarity	NPD8312	Approved
0.7429	Intermediate Similarity	NPD8313	Approved
0.7423	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4308	Phase 3
0.7372	Intermediate Similarity	NPD7033	Discontinued
0.7351	Intermediate Similarity	NPD2861	Phase 2
0.7348	Intermediate Similarity	NPD4363	Phase 3
0.7348	Intermediate Similarity	NPD4360	Phase 2
0.7333	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1470	Approved
0.7333	Intermediate Similarity	NPD2797	Approved
0.7329	Intermediate Similarity	NPD7390	Discontinued
0.732	Intermediate Similarity	NPD411	Approved
0.7315	Intermediate Similarity	NPD4749	Approved
0.7314	Intermediate Similarity	NPD7685	Pre-registration
0.7305	Intermediate Similarity	NPD4288	Approved
0.7297	Intermediate Similarity	NPD1201	Approved
0.7297	Intermediate Similarity	NPD422	Phase 1
0.7289	Intermediate Similarity	NPD37	Approved
0.7284	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7228	Approved
0.7279	Intermediate Similarity	NPD17	Approved
0.7268	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3225	Approved
0.7262	Intermediate Similarity	NPD4966	Approved
0.7262	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4965	Approved
0.7262	Intermediate Similarity	NPD4967	Phase 2
0.726	Intermediate Similarity	NPD9545	Approved
0.7255	Intermediate Similarity	NPD4625	Phase 3
0.7251	Intermediate Similarity	NPD5711	Approved
0.7251	Intermediate Similarity	NPD5710	Approved
0.7229	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4287	Approved
0.7219	Intermediate Similarity	NPD3266	Approved
0.7219	Intermediate Similarity	NPD3267	Approved
0.7213	Intermediate Similarity	NPD4361	Phase 2
0.7213	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7458	Discontinued
0.7211	Intermediate Similarity	NPD9268	Approved
0.7209	Intermediate Similarity	NPD5242	Approved
0.7208	Intermediate Similarity	NPD6798	Discontinued
0.7208	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3764	Approved
0.7207	Intermediate Similarity	NPD8434	Phase 2
0.7202	Intermediate Similarity	NPD5353	Approved
0.7188	Intermediate Similarity	NPD2654	Approved
0.7186	Intermediate Similarity	NPD6844	Discontinued
0.7179	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6355	Discontinued
0.7179	Intermediate Similarity	NPD5124	Phase 1
0.7153	Intermediate Similarity	NPD1241	Discontinued
0.7151	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD8166	Discontinued
0.7133	Intermediate Similarity	NPD3972	Approved
0.7123	Intermediate Similarity	NPD9493	Approved
0.7119	Intermediate Similarity	NPD6104	Discontinued
0.7115	Intermediate Similarity	NPD4060	Phase 1
0.7115	Intermediate Similarity	NPD4307	Phase 2
0.7111	Intermediate Similarity	NPD8150	Discontinued
0.7107	Intermediate Similarity	NPD5408	Approved
0.7107	Intermediate Similarity	NPD5406	Approved
0.7107	Intermediate Similarity	NPD5405	Approved
0.7107	Intermediate Similarity	NPD5404	Approved
0.7105	Intermediate Similarity	NPD7584	Approved
0.7102	Intermediate Similarity	NPD1729	Discontinued
0.7101	Intermediate Similarity	NPD2296	Approved
0.7099	Intermediate Similarity	NPD2354	Approved
0.7097	Intermediate Similarity	NPD1296	Phase 2
0.7075	Intermediate Similarity	NPD5536	Phase 2
0.7073	Intermediate Similarity	NPD4661	Approved
0.7073	Intermediate Similarity	NPD4662	Approved
0.7069	Intermediate Similarity	NPD2403	Approved
0.7063	Intermediate Similarity	NPD7266	Discontinued
0.7063	Intermediate Similarity	NPD1471	Phase 3

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