NPASS Compound

Structure

CID219584 OpenBabel06191716012D 29 30 0 0 1 0 0 0 0 0999 V2000 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 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 0.0000 3.0000 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 -3.4641 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 -5.1962 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 1 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 -2.5981 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 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 -1.0000 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 -2.5981 0.5000 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 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 -3.4641 0.0000 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 6 1 0 0 0 0 2 7 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 6 8 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 16 1 0 0 0 0 11 12 1 0 0 0 0 11 14 2 0 0 0 0 12 17 1 0 0 0 0 13 16 2 0 0 0 0 13 18 1 0 0 0 0 15 5 1 1 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 25 2 0 0 0 0 18 29 1 0 0 0 0 19 22 1 0 0 0 0 19 24 2 0 0 0 0 20 21 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 21 26 2 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.22
Volume:	432.043
LogP:	6.642
LogD:	4.254
LogS:	-4.288
# Rotatable Bonds:	9
TPSA:	87.74
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.245
Synthetic Accessibility Score:	3.404
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.77
MDCK Permeability:	2.1128988009877503e-05
Pgp-inhibitor:	0.766
Pgp-substrate:	0.067
Human Intestinal Absorption (HIA):	0.047
20% Bioavailability (F20%):	0.739
30% Bioavailability (F30%):	0.451

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	98.08000946044922%
Volume Distribution (VD):	1.556
Pgp-substrate:	4.343690395355225%

ADMET: Metabolism

CYP1A2-inhibitor:	0.542
CYP1A2-substrate:	0.655
CYP2C19-inhibitor:	0.874
CYP2C19-substrate:	0.133
CYP2C9-inhibitor:	0.843
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.473
CYP2D6-substrate:	0.262
CYP3A4-inhibitor:	0.212
CYP3A4-substrate:	0.139

ADMET: Excretion

Clearance (CL):	9.057
Half-life (T1/2):	0.117

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.811
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.066
Rat Oral Acute Toxicity:	0.488
Maximum Recommended Daily Dose:	0.144
Skin Sensitization:	0.602
Carcinogencity:	0.133
Eye Corrosion:	0.003
Eye Irritation:	0.106
Respiratory Toxicity:	0.601

Download Data

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

Natural Product: NPC219584

Natural Product ID:	NPC219584
*Common Name:**	Mammea C/Bb
IUPAC Name:	5,7-dihydroxy-8-[(2S)-2-methylbutanoyl]-6-(3-methylbut-2-enyl)-4-pentylchromen-2-one
Synonyms:
Standard InCHIKey:	HHPBGHOULCFTMR-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C24H32O5/c1-6-8-9-10-16-13-18(25)29-24-19(16)22(27)17(12-11-14(3)4)23(28)20(24)21(26)15(5)7-2/h11,13,15,27-28H,6-10,12H2,1-5H3/t15-/m0/s1
SMILES:	CCCCCc1cc(=O)oc2c1c(O)c(CC=C(C)C)c(c2C(=O)[C@H](CC)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689180
PubChem CID:	53324072
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0002908] Hydroxycoumarins [CHEMONTID:0002909] 7-hydroxycoumarins

*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
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[21214226]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21214226]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21645	Mammea americana	Species	Calophyllaceae	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	4

Activity Type	# Activity
Cell Line	2
PROTEIN FAMILY	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	1560.0	nM	PMID[537105]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	2190.0	nM	PMID[537105]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	3730.0	nM	PMID[537105]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	3400.0	nM	PMID[537105]

☑ 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 NPC219584 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	370
0.1-0.2	1618
0.2-0.3	4031
0.3-0.4	9817
0.4-0.5	8902
0.5-0.6	3951
0.6-0.7	6074
0.7-0.8	4759
0.8-0.85	1965
0.85-0.9	959
0.9-0.95	203
0.95-1	48

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470083
0.9925	High Similarity	NPC19476
0.9925	High Similarity	NPC241975
0.9924	High Similarity	NPC138047
0.9924	High Similarity	NPC474624
0.9924	High Similarity	NPC131782
0.985	High Similarity	NPC183639
0.985	High Similarity	NPC199458
0.9635	High Similarity	NPC470553
0.9635	High Similarity	NPC307895
0.9632	High Similarity	NPC470555
0.9565	High Similarity	NPC469935
0.9565	High Similarity	NPC118059
0.9565	High Similarity	NPC288910
0.9565	High Similarity	NPC470554
0.9565	High Similarity	NPC133060
0.9565	High Similarity	NPC178627
0.9562	High Similarity	NPC470556
0.9562	High Similarity	NPC112829
0.9559	High Similarity	NPC221173
0.9496	High Similarity	NPC181388
0.9496	High Similarity	NPC470910
0.9493	High Similarity	NPC196459
0.9493	High Similarity	NPC33653
0.9493	High Similarity	NPC112791
0.9493	High Similarity	NPC184738
0.9493	High Similarity	NPC94794
0.9493	High Similarity	NPC188632
0.9493	High Similarity	NPC470296
0.9493	High Similarity	NPC87609
0.9493	High Similarity	NPC470909
0.9493	High Similarity	NPC96216
0.9493	High Similarity	NPC474939
0.9485	High Similarity	NPC472343
0.947	High Similarity	NPC185624
0.9424	High Similarity	NPC1886
0.9424	High Similarity	NPC196137
0.942	High Similarity	NPC294432
0.942	High Similarity	NPC36181
0.9362	High Similarity	NPC469933
0.9357	High Similarity	NPC470322
0.9357	High Similarity	NPC154217
0.9333	High Similarity	NPC101752
0.9328	High Similarity	NPC470984
0.9318	High Similarity	NPC21378
0.9318	High Similarity	NPC470987
0.9296	High Similarity	NPC469932
0.9291	High Similarity	NPC297886
0.9291	High Similarity	NPC249942
0.9281	High Similarity	NPC472344
0.927	High Similarity	NPC470668
0.927	High Similarity	NPC470669
0.9265	High Similarity	NPC470982
0.9265	High Similarity	NPC174999
0.9265	High Similarity	NPC470983
0.9254	High Similarity	NPC470988
0.9225	High Similarity	NPC208303
0.9225	High Similarity	NPC161864
0.922	High Similarity	NPC57470
0.9197	High Similarity	NPC332594
0.9185	High Similarity	NPC93756
0.9185	High Similarity	NPC108113
0.9161	High Similarity	NPC19238
0.9155	High Similarity	NPC140120
0.9155	High Similarity	NPC180477
0.9155	High Similarity	NPC474108
0.9155	High Similarity	NPC177995
0.9155	High Similarity	NPC285748
0.9149	High Similarity	NPC71184
0.9149	High Similarity	NPC469953
0.9149	High Similarity	NPC206212
0.9137	High Similarity	NPC16455
0.9137	High Similarity	NPC477272
0.9137	High Similarity	NPC471587
0.9137	High Similarity	NPC307990
0.913	High Similarity	NPC474487
0.913	High Similarity	NPC470672
0.913	High Similarity	NPC131130
0.913	High Similarity	NPC474504
0.913	High Similarity	NPC470671
0.9124	High Similarity	NPC156910
0.9124	High Similarity	NPC470985
0.9124	High Similarity	NPC470989
0.9124	High Similarity	NPC268081
0.9118	High Similarity	NPC125920
0.9111	High Similarity	NPC10971
0.9097	High Similarity	NPC327059
0.9097	High Similarity	NPC470908
0.9097	High Similarity	NPC474735
0.9097	High Similarity	NPC321387
0.9071	High Similarity	NPC282300
0.9071	High Similarity	NPC316911
0.9071	High Similarity	NPC316560
0.9065	High Similarity	NPC217186
0.9065	High Similarity	NPC55018
0.9065	High Similarity	NPC240305
0.9065	High Similarity	NPC96565
0.9065	High Similarity	NPC216978
0.9065	High Similarity	NPC220062
0.9065	High Similarity	NPC139554
0.9065	High Similarity	NPC473209
0.9065	High Similarity	NPC53181
0.9065	High Similarity	NPC301217
0.9065	High Similarity	NPC303633
0.9065	High Similarity	NPC23257
0.9058	High Similarity	NPC253616
0.9058	High Similarity	NPC38153
0.9051	High Similarity	NPC60667
0.9044	High Similarity	NPC16197
0.9034	High Similarity	NPC290671
0.9028	High Similarity	NPC104236
0.9028	High Similarity	NPC164205
0.9007	High Similarity	NPC321148
0.9007	High Similarity	NPC321629
0.9007	High Similarity	NPC204469
0.9007	High Similarity	NPC323884
0.9007	High Similarity	NPC326193
0.9	High Similarity	NPC241100
0.9	High Similarity	NPC172986
0.9	High Similarity	NPC270883
0.9	High Similarity	NPC261227
0.9	High Similarity	NPC159275
0.8993	High Similarity	NPC272844
0.8993	High Similarity	NPC254168
0.8993	High Similarity	NPC248995
0.8993	High Similarity	NPC54820
0.8993	High Similarity	NPC201395
0.8993	High Similarity	NPC36414
0.8993	High Similarity	NPC268178
0.8993	High Similarity	NPC180501
0.898	High Similarity	NPC469934
0.8978	High Similarity	NPC144027
0.8978	High Similarity	NPC236974
0.8971	High Similarity	NPC215875
0.8971	High Similarity	NPC285054
0.8971	High Similarity	NPC15834
0.8971	High Similarity	NPC25937
0.8966	High Similarity	NPC158866
0.8966	High Similarity	NPC151973
0.8963	High Similarity	NPC5515
0.8963	High Similarity	NPC270369
0.8936	High Similarity	NPC64908
0.8936	High Similarity	NPC156590
0.8936	High Similarity	NPC118840
0.8936	High Similarity	NPC110969
0.8936	High Similarity	NPC147688
0.8936	High Similarity	NPC205006
0.8936	High Similarity	NPC201820
0.8929	High Similarity	NPC78913
0.8929	High Similarity	NPC470986
0.8929	High Similarity	NPC18260
0.8929	High Similarity	NPC472515
0.8921	High Similarity	NPC255801
0.8921	High Similarity	NPC322301
0.8913	High Similarity	NPC151113
0.8904	High Similarity	NPC312549
0.8904	High Similarity	NPC209142
0.8897	High Similarity	NPC31872
0.8897	High Similarity	NPC473584
0.8897	High Similarity	NPC475589
0.8881	High Similarity	NPC473014
0.8881	High Similarity	NPC29577
0.8881	High Similarity	NPC235217
0.8881	High Similarity	NPC326500
0.8873	High Similarity	NPC299080
0.8873	High Similarity	NPC11561
0.8873	High Similarity	NPC266725
0.8873	High Similarity	NPC217083
0.8873	High Similarity	NPC78803
0.8873	High Similarity	NPC276565
0.8873	High Similarity	NPC293852
0.8873	High Similarity	NPC226636
0.8873	High Similarity	NPC59739
0.8873	High Similarity	NPC214236
0.8873	High Similarity	NPC200694
0.8873	High Similarity	NPC62840
0.8873	High Similarity	NPC325346
0.8865	High Similarity	NPC150522
0.8865	High Similarity	NPC69769
0.8865	High Similarity	NPC235239
0.8865	High Similarity	NPC305355
0.8865	High Similarity	NPC475680
0.8849	High Similarity	NPC470397
0.8849	High Similarity	NPC187826
0.8849	High Similarity	NPC470398
0.8849	High Similarity	NPC13408
0.8841	High Similarity	NPC103842
0.8836	High Similarity	NPC180351
0.8832	High Similarity	NPC203817
0.8828	High Similarity	NPC472345
0.8828	High Similarity	NPC37139
0.8828	High Similarity	NPC105415
0.8824	High Similarity	NPC250057
0.8824	High Similarity	NPC279566
0.8824	High Similarity	NPC324482
0.8819	High Similarity	NPC285630
0.8819	High Similarity	NPC476088
0.8819	High Similarity	NPC237208
0.8819	High Similarity	NPC329678
0.8819	High Similarity	NPC153758

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 NPC219584 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	330
0.1-0.2	986
0.2-0.3	1670
0.3-0.4	2634
0.4-0.5	1894
0.5-0.6	1122
0.6-0.7	338
0.7-0.8	118
0.8-0.85	41
0.85-0.9	12
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8768	High Similarity	NPD6651	Approved
0.875	High Similarity	NPD4378	Clinical (unspecified phase)
0.875	High Similarity	NPD7410	Clinical (unspecified phase)
0.8662	High Similarity	NPD2800	Approved
0.8592	High Similarity	NPD970	Clinical (unspecified phase)
0.8531	High Similarity	NPD1243	Approved
0.8523	High Similarity	NPD7411	Suspended
0.8493	Intermediate Similarity	NPD2532	Approved
0.8493	Intermediate Similarity	NPD2533	Approved
0.8493	Intermediate Similarity	NPD2534	Approved
0.8487	Intermediate Similarity	NPD7075	Discontinued
0.8411	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD7819	Suspended
0.8392	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8357	Intermediate Similarity	NPD1240	Approved
0.8355	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6801	Discontinued
0.8333	Intermediate Similarity	NPD1549	Phase 2
0.8299	Intermediate Similarity	NPD6799	Approved
0.8252	Intermediate Similarity	NPD1510	Phase 2
0.8239	Intermediate Similarity	NPD1607	Approved
0.8219	Intermediate Similarity	NPD3750	Approved
0.8214	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD2796	Approved
0.8182	Intermediate Similarity	NPD7768	Phase 2
0.817	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD5124	Phase 1
0.8151	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD920	Approved
0.8125	Intermediate Similarity	NPD2799	Discontinued
0.8108	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD6599	Discontinued
0.8092	Intermediate Similarity	NPD4380	Phase 2
0.8088	Intermediate Similarity	NPD422	Phase 1
0.8054	Intermediate Similarity	NPD1511	Approved
0.805	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD9717	Approved
0.8013	Intermediate Similarity	NPD3749	Approved
0.8	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1203	Approved
0.7973	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD3268	Approved
0.7958	Intermediate Similarity	NPD2313	Discontinued
0.7947	Intermediate Similarity	NPD1512	Approved
0.7945	Intermediate Similarity	NPD2935	Discontinued
0.7945	Intermediate Similarity	NPD1551	Phase 2
0.7935	Intermediate Similarity	NPD2801	Approved
0.7901	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD7286	Phase 2
0.7898	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD7473	Discontinued
0.7885	Intermediate Similarity	NPD3817	Phase 2
0.7877	Intermediate Similarity	NPD3748	Approved
0.7871	Intermediate Similarity	NPD1934	Approved
0.7857	Intermediate Similarity	NPD2797	Approved
0.7817	Intermediate Similarity	NPD6832	Phase 2
0.7812	Intermediate Similarity	NPD5710	Approved
0.7812	Intermediate Similarity	NPD5711	Approved
0.7805	Intermediate Similarity	NPD5953	Discontinued
0.7778	Intermediate Similarity	NPD5403	Approved
0.775	Intermediate Similarity	NPD6959	Discontinued
0.7736	Intermediate Similarity	NPD919	Approved
0.7722	Intermediate Similarity	NPD3882	Suspended
0.7708	Intermediate Similarity	NPD1296	Phase 2
0.7703	Intermediate Similarity	NPD6099	Approved
0.7703	Intermediate Similarity	NPD6100	Approved
0.7702	Intermediate Similarity	NPD6232	Discontinued
0.7677	Intermediate Similarity	NPD3226	Approved
0.7647	Intermediate Similarity	NPD5401	Approved
0.761	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD3267	Approved
0.7606	Intermediate Similarity	NPD3266	Approved
0.7605	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7054	Approved
0.7535	Intermediate Similarity	NPD3225	Approved
0.7533	Intermediate Similarity	NPD2346	Discontinued
0.7533	Intermediate Similarity	NPD2344	Approved
0.753	Intermediate Similarity	NPD7472	Approved
0.753	Intermediate Similarity	NPD7074	Phase 3
0.7517	Intermediate Similarity	NPD7033	Discontinued
0.7517	Intermediate Similarity	NPD4308	Phase 3
0.7515	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5844	Phase 1
0.7469	Intermediate Similarity	NPD5494	Approved
0.7468	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD411	Approved
0.744	Intermediate Similarity	NPD7251	Discontinued
0.744	Intermediate Similarity	NPD6559	Discontinued
0.7438	Intermediate Similarity	NPD5402	Approved
0.7434	Intermediate Similarity	NPD2654	Approved
0.7432	Intermediate Similarity	NPD447	Suspended
0.7431	Intermediate Similarity	NPD2798	Approved
0.741	Intermediate Similarity	NPD9545	Approved
0.74	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7808	Phase 3
0.7396	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1608	Approved
0.7391	Intermediate Similarity	NPD9493	Approved
0.7386	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6797	Phase 2
0.7375	Intermediate Similarity	NPD1465	Phase 2
0.7347	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2309	Approved
0.7329	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD230	Phase 1
0.731	Intermediate Similarity	NPD1019	Discontinued
0.7248	Intermediate Similarity	NPD943	Approved
0.7248	Intermediate Similarity	NPD4307	Phase 2
0.7244	Intermediate Similarity	NPD7390	Discontinued
0.7233	Intermediate Similarity	NPD7458	Discontinued
0.723	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4288	Approved
0.7212	Intermediate Similarity	NPD1247	Approved
0.7211	Intermediate Similarity	NPD4908	Phase 1
0.72	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6004	Phase 3
0.719	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6002	Phase 3
0.719	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6005	Phase 3
0.7188	Intermediate Similarity	NPD6585	Discontinued
0.7183	Intermediate Similarity	NPD17	Approved
0.7176	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4363	Phase 3
0.7175	Intermediate Similarity	NPD4360	Phase 2
0.7169	Intermediate Similarity	NPD7229	Phase 3
0.7163	Intermediate Similarity	NPD1548	Phase 1
0.7152	Intermediate Similarity	NPD5049	Phase 3
0.7143	Intermediate Similarity	NPD4287	Approved
0.7143	Intermediate Similarity	NPD5889	Approved
0.7143	Intermediate Similarity	NPD5890	Approved
0.7135	Intermediate Similarity	NPD4361	Phase 2
0.7135	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5405	Approved
0.7124	Intermediate Similarity	NPD5406	Approved
0.7124	Intermediate Similarity	NPD5404	Approved
0.7124	Intermediate Similarity	NPD5408	Approved
0.7123	Intermediate Similarity	NPD1164	Approved
0.7118	Intermediate Similarity	NPD1729	Discontinued
0.7113	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4749	Approved
0.7097	Intermediate Similarity	NPD1652	Phase 2
0.7089	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6355	Discontinued
0.7086	Intermediate Similarity	NPD1933	Approved
0.7083	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1610	Phase 2
0.7051	Intermediate Similarity	NPD7003	Approved
0.7035	Intermediate Similarity	NPD6104	Discontinued
0.7034	Intermediate Similarity	NPD1481	Phase 2
0.7024	Intermediate Similarity	NPD3926	Phase 2
0.7019	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2354	Approved
0.7	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3764	Approved
0.7	Intermediate Similarity	NPD6798	Discontinued
0.7	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2403	Approved
0.6982	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1535	Discovery
0.6966	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8312	Approved
0.6954	Remote Similarity	NPD8313	Approved
0.6934	Remote Similarity	NPD74	Approved
0.6934	Remote Similarity	NPD9266	Approved
0.6933	Remote Similarity	NPD4625	Phase 3
0.6929	Remote Similarity	NPD1241	Discontinued
0.6923	Remote Similarity	NPD1894	Discontinued
0.6918	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3972	Approved
0.6908	Remote Similarity	NPD4060	Phase 1
0.6905	Remote Similarity	NPD7199	Phase 2
0.6903	Remote Similarity	NPD4477	Approved
0.6903	Remote Similarity	NPD4476	Approved
0.6867	Remote Similarity	NPD2614	Approved
0.6861	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD9267	Approved
0.6861	Remote Similarity	NPD9263	Approved
0.6861	Remote Similarity	NPD9264	Approved
0.6859	Remote Similarity	NPD2353	Approved
0.6859	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5535	Approved
0.6855	Remote Similarity	NPD6666	Approved
0.6855	Remote Similarity	NPD6667	Approved
0.6854	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7584	Approved
0.6842	Remote Similarity	NPD8032	Phase 2
0.6839	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD8434	Phase 2
0.6832	Remote Similarity	NPD6273	Approved
0.6828	Remote Similarity	NPD4626	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