NPASS Compound

Structure

CID22467 OpenBabel06191715352D 23 25 0 0 1 0 0 0 0 0999 V2000 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 2.5981 1.5000 0.0000 C 0 0 0 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 1.7321 1.0000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -1.7321 0.0000 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 0.8660 -0.5000 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 -1.7321 -2.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 21 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 11 2 0 0 0 0 7 11 1 0 0 0 0 8 13 1 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 10 19 2 0 0 0 0 12 15 1 0 0 0 0 12 18 2 0 0 0 0 13 17 1 0 0 0 0 13 20 2 0 0 0 0 14 11 1 6 0 0 0 14 23 1 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.1
Volume:	317.074
LogP:	2.831
LogD:	2.493
LogS:	-4.98
# Rotatable Bonds:	4
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.811
Synthetic Accessibility Score:	2.929
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.571
MDCK Permeability:	2.222383045591414e-05
Pgp-inhibitor:	0.681
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.865
Plasma Protein Binding (PPB):	81.87748718261719%
Volume Distribution (VD):	1.085
Pgp-substrate:	9.568921089172363%

ADMET: Metabolism

CYP1A2-inhibitor:	0.552
CYP1A2-substrate:	0.796
CYP2C19-inhibitor:	0.922
CYP2C19-substrate:	0.83
CYP2C9-inhibitor:	0.78
CYP2C9-substrate:	0.833
CYP2D6-inhibitor:	0.154
CYP2D6-substrate:	0.683
CYP3A4-inhibitor:	0.629
CYP3A4-substrate:	0.435

ADMET: Excretion

Clearance (CL):	5.744
Half-life (T1/2):	0.166

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.237
Drug-inuced Liver Injury (DILI):	0.843
AMES Toxicity:	0.331
Rat Oral Acute Toxicity:	0.874
Maximum Recommended Daily Dose:	0.406
Skin Sensitization:	0.275
Carcinogencity:	0.874
Eye Corrosion:	0.005
Eye Irritation:	0.801
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC22467

Natural Product ID:	NPC22467
*Common Name:**	(2S)-5,7-Dimethoxy-8-Formylflavanone
IUPAC Name:	(2S)-5,7-dimethoxy-4-oxo-2-phenyl-2,3-dihydrochromene-8-carbaldehyde
Synonyms:
Standard InCHIKey:	FHKQMPVRIQJSEJ-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C18H16O5/c1-21-15-9-16(22-2)17-13(20)8-14(11-6-4-3-5-7-11)23-18(17)12(15)10-19/h3-7,9-10,14H,8H2,1-2H3/t14-/m0/s1
SMILES:	COc1cc(c2C(=O)C[C@@H](c3ccccc3)Oc2c1C=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454070
PubChem CID:	10335676
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	stem bark	Indonesia	1999-SEP	PMID[14510596]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[14510596]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	dry stem	n.a.	n.a.	PMID[25466192]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29482940]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19432	Millettia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19432	Millettia pinnata	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	1
Others	2

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	2.6	ug ml-1	PMID[490391]
NPT27	Others	Unspecified		IC50	>	10.0	ug.mL-1	PMID[490391]
NPT2	Others	Unspecified		Ratio	>	3.9	n.a.	PMID[490391]

☑ 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 NPC22467 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	441
0.1-0.2	1758
0.2-0.3	4717
0.3-0.4	12011
0.4-0.5	5908
0.5-0.6	4506
0.6-0.7	6089
0.7-0.8	4804
0.8-0.85	1460
0.85-0.9	821
0.9-0.95	170
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9704	High Similarity	NPC259685
0.9571	High Similarity	NPC2416
0.9571	High Similarity	NPC476153
0.9571	High Similarity	NPC215885
0.9562	High Similarity	NPC11566
0.9556	High Similarity	NPC99854
0.95	High Similarity	NPC110776
0.95	High Similarity	NPC271590
0.9371	High Similarity	NPC214493
0.9357	High Similarity	NPC182852
0.9357	High Similarity	NPC37496
0.9357	High Similarity	NPC227579
0.9357	High Similarity	NPC10937
0.9357	High Similarity	NPC40833
0.9357	High Similarity	NPC64915
0.9357	High Similarity	NPC167624
0.9357	High Similarity	NPC107572
0.9357	High Similarity	NPC76338
0.9357	High Similarity	NPC223500
0.9357	High Similarity	NPC1089
0.9357	High Similarity	NPC265040
0.9357	High Similarity	NPC78
0.9357	High Similarity	NPC177354
0.9357	High Similarity	NPC76372
0.9357	High Similarity	NPC32739
0.9357	High Similarity	NPC324436
0.9357	High Similarity	NPC161506
0.9357	High Similarity	NPC194432
0.9357	High Similarity	NPC66515
0.9357	High Similarity	NPC147145
0.9357	High Similarity	NPC306829
0.9357	High Similarity	NPC328164
0.9357	High Similarity	NPC148757
0.9357	High Similarity	NPC125855
0.9357	High Similarity	NPC166482
0.9357	High Similarity	NPC296917
0.9357	High Similarity	NPC324134
0.9357	High Similarity	NPC166934
0.9357	High Similarity	NPC228504
0.9357	High Similarity	NPC220998
0.9353	High Similarity	NPC472409
0.9343	High Similarity	NPC161196
0.9338	High Similarity	NPC125269
0.9291	High Similarity	NPC81697
0.9291	High Similarity	NPC143896
0.9291	High Similarity	NPC39329
0.9291	High Similarity	NPC169591
0.9291	High Similarity	NPC310130
0.9291	High Similarity	NPC316816
0.9291	High Similarity	NPC150408
0.9291	High Similarity	NPC478086
0.9291	High Similarity	NPC175504
0.9291	High Similarity	NPC221432
0.9291	High Similarity	NPC91560
0.9291	High Similarity	NPC185276
0.9291	High Similarity	NPC75049
0.9291	High Similarity	NPC164980
0.9291	High Similarity	NPC149026
0.9291	High Similarity	NPC214166
0.9291	High Similarity	NPC107177
0.9291	High Similarity	NPC257097
0.9291	High Similarity	NPC59522
0.9291	High Similarity	NPC125894
0.9291	High Similarity	NPC68104
0.9291	High Similarity	NPC278249
0.9291	High Similarity	NPC223812
0.9291	High Similarity	NPC471621
0.9291	High Similarity	NPC77794
0.9291	High Similarity	NPC85162
0.9286	High Similarity	NPC166689
0.9286	High Similarity	NPC324386
0.9286	High Similarity	NPC4743
0.9286	High Similarity	NPC52576
0.9286	High Similarity	NPC279650
0.9286	High Similarity	NPC17170
0.9286	High Similarity	NPC258630
0.9286	High Similarity	NPC110038
0.9286	High Similarity	NPC213322
0.9286	High Similarity	NPC156190
0.9286	High Similarity	NPC248372
0.9286	High Similarity	NPC96408
0.9286	High Similarity	NPC312391
0.9225	High Similarity	NPC236766
0.9225	High Similarity	NPC131579
0.9225	High Similarity	NPC473014
0.9225	High Similarity	NPC473015
0.9225	High Similarity	NPC197252
0.9225	High Similarity	NPC209040
0.9225	High Similarity	NPC473013
0.9225	High Similarity	NPC124780
0.9225	High Similarity	NPC87486
0.9225	High Similarity	NPC131568
0.9225	High Similarity	NPC235217
0.9214	High Similarity	NPC188243
0.9214	High Similarity	NPC110228
0.9214	High Similarity	NPC6407
0.9209	High Similarity	NPC17848
0.9203	High Similarity	NPC254741
0.9191	High Similarity	NPC101294
0.9191	High Similarity	NPC473655
0.9161	High Similarity	NPC470131
0.9161	High Similarity	NPC111786
0.9161	High Similarity	NPC214774
0.9161	High Similarity	NPC475052
0.9161	High Similarity	NPC20488
0.9161	High Similarity	NPC312973
0.9161	High Similarity	NPC473078
0.9161	High Similarity	NPC83357
0.9161	High Similarity	NPC267375
0.9161	High Similarity	NPC109183
0.9161	High Similarity	NPC285630
0.9161	High Similarity	NPC54577
0.9161	High Similarity	NPC246948
0.9161	High Similarity	NPC127059
0.9161	High Similarity	NPC142405
0.9161	High Similarity	NPC67805
0.9161	High Similarity	NPC301276
0.9161	High Similarity	NPC176229
0.9161	High Similarity	NPC195621
0.9161	High Similarity	NPC470132
0.9161	High Similarity	NPC472629
0.9161	High Similarity	NPC470134
0.9161	High Similarity	NPC88964
0.9161	High Similarity	NPC470133
0.9161	High Similarity	NPC470647
0.9149	High Similarity	NPC3188
0.9143	High Similarity	NPC274784
0.9143	High Similarity	NPC265871
0.9143	High Similarity	NPC222342
0.9143	High Similarity	NPC20709
0.9143	High Similarity	NPC310135
0.9143	High Similarity	NPC140890
0.9143	High Similarity	NPC329203
0.9143	High Similarity	NPC150648
0.9143	High Similarity	NPC225153
0.913	High Similarity	NPC46869
0.9118	High Similarity	NPC278556
0.9111	High Similarity	NPC228184
0.9097	High Similarity	NPC283234
0.9097	High Similarity	NPC23728
0.9097	High Similarity	NPC296998
0.9097	High Similarity	NPC472627
0.9097	High Similarity	NPC110303
0.9097	High Similarity	NPC473077
0.9097	High Similarity	NPC300988
0.9097	High Similarity	NPC471285
0.9097	High Similarity	NPC10990
0.9091	High Similarity	NPC470135
0.9091	High Similarity	NPC470890
0.9091	High Similarity	NPC271288
0.9091	High Similarity	NPC470136
0.9091	High Similarity	NPC39045
0.9091	High Similarity	NPC319752
0.9078	High Similarity	NPC76445
0.9078	High Similarity	NPC150522
0.9078	High Similarity	NPC284550
0.9078	High Similarity	NPC69769
0.9078	High Similarity	NPC159275
0.9078	High Similarity	NPC129853
0.9078	High Similarity	NPC241100
0.9041	High Similarity	NPC148423
0.9041	High Similarity	NPC135303
0.9034	High Similarity	NPC160821
0.9034	High Similarity	NPC476342
0.9034	High Similarity	NPC132592
0.9034	High Similarity	NPC161191
0.9028	High Similarity	NPC187282
0.9028	High Similarity	NPC228779
0.9028	High Similarity	NPC474161
0.9028	High Similarity	NPC476088
0.9028	High Similarity	NPC290133
0.9028	High Similarity	NPC24136
0.9021	High Similarity	NPC166138
0.9021	High Similarity	NPC18585
0.9021	High Similarity	NPC106985
0.9014	High Similarity	NPC103362
0.9014	High Similarity	NPC110969
0.9014	High Similarity	NPC282300
0.9007	High Similarity	NPC96565
0.9007	High Similarity	NPC220062
0.9007	High Similarity	NPC217186
0.9007	High Similarity	NPC55018
0.9007	High Similarity	NPC216978
0.9007	High Similarity	NPC78913
0.9007	High Similarity	NPC18260
0.9007	High Similarity	NPC301217
0.9007	High Similarity	NPC303633
0.9007	High Similarity	NPC53181
0.9	High Similarity	NPC243083
0.9	High Similarity	NPC32441
0.9	High Similarity	NPC287246
0.9	High Similarity	NPC296490
0.9	High Similarity	NPC295261
0.9	High Similarity	NPC12296
0.9	High Similarity	NPC157855
0.9	High Similarity	NPC13768
0.9	High Similarity	NPC107586
0.9	High Similarity	NPC79943
0.8986	High Similarity	NPC292998
0.8986	High Similarity	NPC122365

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 NPC22467 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	389
0.1-0.2	1001
0.2-0.3	1614
0.3-0.4	2727
0.4-0.5	1783
0.5-0.6	1102
0.6-0.7	376
0.7-0.8	113
0.8-0.85	30
0.85-0.9	13
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9203	High Similarity	NPD2796	Approved
0.9	High Similarity	NPD1550	Clinical (unspecified phase)
0.9	High Similarity	NPD1552	Clinical (unspecified phase)
0.898	High Similarity	NPD7411	Suspended
0.8936	High Similarity	NPD1549	Phase 2
0.8926	High Similarity	NPD8443	Clinical (unspecified phase)
0.8828	High Similarity	NPD4378	Clinical (unspecified phase)
0.8733	High Similarity	NPD2393	Clinical (unspecified phase)
0.8733	High Similarity	NPD7096	Clinical (unspecified phase)
0.8609	High Similarity	NPD7819	Suspended
0.8571	High Similarity	NPD7410	Clinical (unspecified phase)
0.8562	High Similarity	NPD7075	Discontinued
0.8543	High Similarity	NPD6801	Discontinued
0.8533	High Similarity	NPD4380	Phase 2
0.8503	High Similarity	NPD6799	Approved
0.8483	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD1510	Phase 2
0.8456	Intermediate Similarity	NPD920	Approved
0.8452	Intermediate Similarity	NPD5494	Approved
0.844	Intermediate Similarity	NPD1240	Approved
0.8435	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1934	Approved
0.8354	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1607	Approved
0.8322	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8309	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD6599	Discontinued
0.8231	Intermediate Similarity	NPD1243	Approved
0.8205	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD1247	Approved
0.8165	Intermediate Similarity	NPD6959	Discontinued
0.8086	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD3748	Approved
0.8077	Intermediate Similarity	NPD3817	Phase 2
0.8038	Intermediate Similarity	NPD919	Approved
0.8028	Intermediate Similarity	NPD6832	Phase 2
0.8027	Intermediate Similarity	NPD1551	Phase 2
0.8025	Intermediate Similarity	NPD7768	Phase 2
0.8013	Intermediate Similarity	NPD1511	Approved
0.8013	Intermediate Similarity	NPD2801	Approved
0.8012	Intermediate Similarity	NPD6166	Phase 2
0.8012	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD5403	Approved
0.7961	Intermediate Similarity	NPD5401	Approved
0.7939	Intermediate Similarity	NPD6559	Discontinued
0.7911	Intermediate Similarity	NPD3882	Suspended
0.7908	Intermediate Similarity	NPD1512	Approved
0.7867	Intermediate Similarity	NPD2800	Approved
0.7838	Intermediate Similarity	NPD2799	Discontinued
0.7823	Intermediate Similarity	NPD6651	Approved
0.7818	Intermediate Similarity	NPD7074	Phase 3
0.7817	Intermediate Similarity	NPD3266	Approved
0.7817	Intermediate Similarity	NPD3267	Approved
0.7815	Intermediate Similarity	NPD3750	Approved
0.7771	Intermediate Similarity	NPD5890	Approved
0.7771	Intermediate Similarity	NPD5889	Approved
0.7758	Intermediate Similarity	NPD7054	Approved
0.775	Intermediate Similarity	NPD3749	Approved
0.7748	Intermediate Similarity	NPD2654	Approved
0.7711	Intermediate Similarity	NPD7472	Approved
0.7697	Intermediate Similarity	NPD3818	Discontinued
0.7688	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD3268	Approved
0.7671	Intermediate Similarity	NPD2313	Discontinued
0.7671	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2935	Discontinued
0.7665	Intermediate Similarity	NPD5953	Discontinued
0.7665	Intermediate Similarity	NPD6797	Phase 2
0.7651	Intermediate Similarity	NPD5844	Phase 1
0.7651	Intermediate Similarity	NPD7286	Phase 2
0.7643	Intermediate Similarity	NPD3226	Approved
0.7635	Intermediate Similarity	NPD1933	Approved
0.7625	Intermediate Similarity	NPD5402	Approved
0.7622	Intermediate Similarity	NPD3926	Phase 2
0.7619	Intermediate Similarity	NPD7251	Discontinued
0.7613	Intermediate Similarity	NPD2534	Approved
0.7613	Intermediate Similarity	NPD2532	Approved
0.7613	Intermediate Similarity	NPD2533	Approved
0.7606	Intermediate Similarity	NPD3972	Approved
0.76	Intermediate Similarity	NPD7033	Discontinued
0.7595	Intermediate Similarity	NPD6585	Discontinued
0.759	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4628	Phase 3
0.7574	Intermediate Similarity	NPD7808	Phase 3
0.7561	Intermediate Similarity	NPD6232	Discontinued
0.7547	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD4908	Phase 1
0.753	Intermediate Similarity	NPD7473	Discontinued
0.7518	Intermediate Similarity	NPD1241	Discontinued
0.7517	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD5124	Phase 1
0.7517	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2798	Approved
0.7516	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD1471	Phase 3
0.75	Intermediate Similarity	NPD2346	Discontinued
0.7471	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1203	Approved
0.7443	Intermediate Similarity	NPD4363	Phase 3
0.7443	Intermediate Similarity	NPD4360	Phase 2
0.7434	Intermediate Similarity	NPD6099	Approved
0.7434	Intermediate Similarity	NPD6100	Approved
0.7432	Intermediate Similarity	NPD1296	Phase 2
0.7413	Intermediate Similarity	NPD1610	Phase 2
0.7397	Intermediate Similarity	NPD1019	Discontinued
0.7376	Intermediate Similarity	NPD1548	Phase 1
0.7368	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2403	Approved
0.7361	Intermediate Similarity	NPD9717	Approved
0.7349	Intermediate Similarity	NPD6808	Phase 2
0.7333	Intermediate Similarity	NPD4307	Phase 2
0.7333	Intermediate Similarity	NPD3140	Approved
0.7333	Intermediate Similarity	NPD3142	Approved
0.7329	Intermediate Similarity	NPD2797	Approved
0.7315	Intermediate Similarity	NPD6798	Discontinued
0.7308	Intermediate Similarity	NPD3887	Approved
0.7308	Intermediate Similarity	NPD2309	Approved
0.7278	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD17	Approved
0.7273	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3225	Approved
0.7251	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD943	Approved
0.7215	Intermediate Similarity	NPD7390	Discontinued
0.7209	Intermediate Similarity	NPD6104	Discontinued
0.7207	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD4361	Phase 2
0.7205	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD1729	Discontinued
0.7178	Intermediate Similarity	NPD6279	Approved
0.7178	Intermediate Similarity	NPD6280	Approved
0.7172	Intermediate Similarity	NPD422	Phase 1
0.717	Intermediate Similarity	NPD4661	Approved
0.717	Intermediate Similarity	NPD4662	Approved
0.7169	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD1876	Approved
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD5710	Approved
0.7133	Intermediate Similarity	NPD4625	Phase 3
0.7123	Intermediate Similarity	NPD1608	Approved
0.7115	Intermediate Similarity	NPD2424	Discontinued
0.7105	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1613	Approved
0.7102	Intermediate Similarity	NPD8434	Phase 2
0.7099	Intermediate Similarity	NPD7458	Discontinued
0.7091	Intermediate Similarity	NPD4288	Approved
0.7083	Intermediate Similarity	NPD1651	Approved
0.7073	Intermediate Similarity	NPD6844	Discontinued
0.7071	Intermediate Similarity	NPD5535	Approved
0.707	Intermediate Similarity	NPD1652	Phase 2
0.7067	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6355	Discontinued
0.7051	Intermediate Similarity	NPD2353	Approved
0.7051	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3787	Discontinued
0.7039	Intermediate Similarity	NPD6233	Phase 2
0.7039	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5760	Phase 2
0.703	Intermediate Similarity	NPD1465	Phase 2
0.703	Intermediate Similarity	NPD8455	Phase 2
0.703	Intermediate Similarity	NPD5761	Phase 2
0.7014	Intermediate Similarity	NPD9545	Approved
0.7005	Intermediate Similarity	NPD7584	Approved
0.6994	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4476	Approved
0.6987	Remote Similarity	NPD4477	Approved
0.6982	Remote Similarity	NPD7199	Phase 2
0.6977	Remote Similarity	NPD3751	Discontinued
0.6954	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4622	Approved
0.6948	Remote Similarity	NPD4618	Approved
0.6932	Remote Similarity	NPD8313	Approved
0.6932	Remote Similarity	NPD8312	Approved
0.6918	Remote Similarity	NPD7003	Approved
0.6914	Remote Similarity	NPD5049	Phase 3
0.6914	Remote Similarity	NPD6273	Approved
0.6902	Remote Similarity	NPD8285	Discontinued
0.6901	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5242	Approved
0.6897	Remote Similarity	NPD1894	Discontinued
0.6894	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7212	Phase 2
0.6894	Remote Similarity	NPD7213	Phase 3
0.6887	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2861	Phase 2
0.6886	Remote Similarity	NPD5353	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