NPASS Compound

Structure

CID288910 OpenBabel06191716092D 30 31 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 6.0622 1.5000 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 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 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 -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 -2.5000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 1 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 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 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 0.8660 3.5000 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 -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 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 13 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 13 2 0 0 0 0 10 15 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 15 22 2 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 17 25 1 6 0 0 0 18 21 1 0 0 0 0 18 26 2 0 0 0 0 19 27 2 0 0 0 0 19 30 1 0 0 0 0 20 22 1 0 0 0 0 20 24 2 0 0 0 0 21 23 2 0 0 0 0 21 24 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.22
Volume:	440.833
LogP:	5.405
LogD:	3.48
LogS:	-3.778
# Rotatable Bonds:	9
TPSA:	107.97
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.296
Synthetic Accessibility Score:	3.592
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:	-4.809
MDCK Permeability:	1.4960260159568861e-05
Pgp-inhibitor:	0.057
Pgp-substrate:	0.922
Human Intestinal Absorption (HIA):	0.218
20% Bioavailability (F20%):	0.428
30% Bioavailability (F30%):	0.914

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	94.85919952392578%
Volume Distribution (VD):	1.131
Pgp-substrate:	5.0284833908081055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.219
CYP1A2-substrate:	0.51
CYP2C19-inhibitor:	0.568
CYP2C19-substrate:	0.137
CYP2C9-inhibitor:	0.851
CYP2C9-substrate:	0.936
CYP2D6-inhibitor:	0.223
CYP2D6-substrate:	0.159
CYP3A4-inhibitor:	0.12
CYP3A4-substrate:	0.062

ADMET: Excretion

Clearance (CL):	9.959
Half-life (T1/2):	0.369

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.688
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.309
Maximum Recommended Daily Dose:	0.424
Skin Sensitization:	0.573
Carcinogencity:	0.167
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.153

Download Data

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

Natural Product: NPC288910

Natural Product ID:	NPC288910
*Common Name:**	5,7-Dihydroxy-4-[(1S)-1-Hydroxypentyl]-8-(3-Methylbutanoyl)-6-(3-Methylbut-2-Enyl)Chromen-2-One
IUPAC Name:	5,7-dihydroxy-4-[(1S)-1-hydroxypentyl]-8-(3-methylbutanoyl)-6-(3-methylbut-2-enyl)chromen-2-one
Synonyms:
Standard InCHIKey:	KDXSRMVJFBSRCC-KRWDZBQOSA-N
Standard InCHI:	InChI=1S/C24H32O6/c1-6-7-8-17(25)16-12-19(27)30-24-20(16)22(28)15(10-9-13(2)3)23(29)21(24)18(26)11-14(4)5/h9,12,14,17,25,28-29H,6-8,10-11H2,1-5H3/t17-/m0/s1
SMILES:	CCCC[C@@H](c1cc(=O)oc2c1c(O)c(CC=C(C)C)c(c2C(=O)CC(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689176
PubChem CID:	51040688
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.	n.a.	n.a.	PMID[21214226]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	n.a.	stem	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	=	910.0	nM	PMID[491411]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	1140.0	nM	PMID[491411]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	1720.0	nM	PMID[491411]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	1810.0	nM	PMID[491411]

☑ 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 NPC288910 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	349
0.1-0.2	1451
0.2-0.3	3611
0.3-0.4	7971
0.4-0.5	10894
0.5-0.6	3961
0.6-0.7	5847
0.7-0.8	4885
0.8-0.85	2512
0.85-0.9	990
0.9-0.95	192
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC133060
1.0	High Similarity	NPC470554
1.0	High Similarity	NPC118059
0.9928	High Similarity	NPC184738
0.9928	High Similarity	NPC474939
0.9928	High Similarity	NPC470910
0.9928	High Similarity	NPC470553
0.9928	High Similarity	NPC307895
0.9928	High Similarity	NPC96216
0.9928	High Similarity	NPC470909
0.9928	High Similarity	NPC33653
0.9855	High Similarity	NPC294432
0.9855	High Similarity	NPC470556
0.9855	High Similarity	NPC112829
0.9638	High Similarity	NPC19476
0.9638	High Similarity	NPC241975
0.9577	High Similarity	NPC285748
0.9571	High Similarity	NPC472344
0.9565	High Similarity	NPC470083
0.9565	High Similarity	NPC199458
0.9565	High Similarity	NPC219584
0.9565	High Similarity	NPC183639
0.9514	High Similarity	NPC470908
0.9514	High Similarity	NPC474735
0.9493	High Similarity	NPC138047
0.9493	High Similarity	NPC474624
0.9493	High Similarity	NPC131782
0.9441	High Similarity	NPC177995
0.9441	High Similarity	NPC474108
0.9379	High Similarity	NPC327059
0.9379	High Similarity	NPC321387
0.9315	High Similarity	NPC290671
0.9241	High Similarity	NPC472345
0.9236	High Similarity	NPC181388
0.9236	High Similarity	NPC470322
0.9231	High Similarity	NPC18886
0.9225	High Similarity	NPC470555
0.922	High Similarity	NPC139554
0.9178	High Similarity	NPC19238
0.9167	High Similarity	NPC178627
0.9167	High Similarity	NPC1886
0.9167	High Similarity	NPC469935
0.9167	High Similarity	NPC224714
0.9167	High Similarity	NPC196137
0.9161	High Similarity	NPC276565
0.9155	High Similarity	NPC221173
0.9122	High Similarity	NPC256141
0.9116	High Similarity	NPC180351
0.9103	High Similarity	NPC154217
0.9097	High Similarity	NPC196459
0.9097	High Similarity	NPC470296
0.9097	High Similarity	NPC87609
0.9097	High Similarity	NPC94794
0.9097	High Similarity	NPC188632
0.9097	High Similarity	NPC112791
0.9091	High Similarity	NPC476508
0.9085	High Similarity	NPC472343
0.9071	High Similarity	NPC101752
0.9067	High Similarity	NPC469936
0.9067	High Similarity	NPC474738
0.9067	High Similarity	NPC475797
0.9067	High Similarity	NPC474609
0.9067	High Similarity	NPC129053
0.9067	High Similarity	NPC109967
0.9067	High Similarity	NPC78554
0.9067	High Similarity	NPC321372
0.9065	High Similarity	NPC470984
0.9058	High Similarity	NPC185624
0.9054	High Similarity	NPC209142
0.9054	High Similarity	NPC312549
0.9048	High Similarity	NPC139966
0.9048	High Similarity	NPC307052
0.9048	High Similarity	NPC104236
0.9048	High Similarity	NPC164205
0.9048	High Similarity	NPC469932
0.9041	High Similarity	NPC473133
0.9041	High Similarity	NPC47388
0.9041	High Similarity	NPC470670
0.9041	High Similarity	NPC91902
0.9034	High Similarity	NPC470890
0.9028	High Similarity	NPC36181
0.9021	High Similarity	NPC471587
0.9021	High Similarity	NPC307990
0.9021	High Similarity	NPC16455
0.9014	High Similarity	NPC131130
0.9007	High Similarity	NPC470397
0.9007	High Similarity	NPC156910
0.9007	High Similarity	NPC470983
0.9007	High Similarity	NPC470982
0.9007	High Similarity	NPC174999
0.9	High Similarity	NPC108937
0.9	High Similarity	NPC279218
0.8993	High Similarity	NPC470988
0.898	High Similarity	NPC469933
0.898	High Similarity	NPC10097
0.898	High Similarity	NPC208303
0.898	High Similarity	NPC161864
0.898	High Similarity	NPC470460
0.8973	High Similarity	NPC472629
0.8958	High Similarity	NPC74397
0.8958	High Similarity	NPC201820
0.8951	High Similarity	NPC23257
0.8936	High Similarity	NPC84699
0.8936	High Similarity	NPC60667
0.8919	High Similarity	NPC470461
0.8919	High Similarity	NPC5173
0.8913	High Similarity	NPC21378
0.8913	High Similarity	NPC470987
0.8912	High Similarity	NPC249942
0.8912	High Similarity	NPC202494
0.8912	High Similarity	NPC140120
0.8912	High Similarity	NPC85773
0.8912	High Similarity	NPC297886
0.8904	High Similarity	NPC294365
0.8904	High Similarity	NPC206212
0.8904	High Similarity	NPC473014
0.8904	High Similarity	NPC235217
0.8904	High Similarity	NPC297788
0.8904	High Similarity	NPC124780
0.8904	High Similarity	NPC71184
0.8904	High Similarity	NPC87486
0.8904	High Similarity	NPC469953
0.8889	High Similarity	NPC477272
0.8882	High Similarity	NPC269495
0.8881	High Similarity	NPC470671
0.8881	High Similarity	NPC470669
0.8881	High Similarity	NPC470672
0.8881	High Similarity	NPC474487
0.8881	High Similarity	NPC474504
0.8881	High Similarity	NPC470668
0.8881	High Similarity	NPC36414
0.8874	High Similarity	NPC469934
0.8873	High Similarity	NPC470398
0.8873	High Similarity	NPC470985
0.8873	High Similarity	NPC470989
0.8873	High Similarity	NPC268081
0.8867	High Similarity	NPC273483
0.8865	High Similarity	NPC125920
0.8865	High Similarity	NPC236974
0.8865	High Similarity	NPC144027
0.8859	High Similarity	NPC38775
0.8859	High Similarity	NPC61258
0.8859	High Similarity	NPC37348
0.8859	High Similarity	NPC476509
0.8857	High Similarity	NPC285054
0.8851	High Similarity	NPC145467
0.8851	High Similarity	NPC240622
0.8851	High Similarity	NPC168085
0.8851	High Similarity	NPC471641
0.8851	High Similarity	NPC471642
0.8851	High Similarity	NPC240253
0.8844	High Similarity	NPC474302
0.8844	High Similarity	NPC474161
0.8844	High Similarity	NPC57470
0.8844	High Similarity	NPC127059
0.8844	High Similarity	NPC470458
0.8844	High Similarity	NPC24136
0.8844	High Similarity	NPC187282
0.8844	High Similarity	NPC290133
0.8844	High Similarity	NPC285630
0.8844	High Similarity	NPC476088
0.8836	High Similarity	NPC125894
0.8836	High Similarity	NPC475705
0.8836	High Similarity	NPC117836
0.8836	High Similarity	NPC185276
0.8836	High Similarity	NPC85162
0.8836	High Similarity	NPC107177
0.8836	High Similarity	NPC223812
0.8836	High Similarity	NPC278249
0.8836	High Similarity	NPC476178
0.8836	High Similarity	NPC77794
0.8836	High Similarity	NPC81697
0.8836	High Similarity	NPC51887
0.8828	High Similarity	NPC110038
0.8828	High Similarity	NPC248372
0.8828	High Similarity	NPC166689
0.8828	High Similarity	NPC282300
0.8828	High Similarity	NPC17170
0.8828	High Similarity	NPC156190
0.8828	High Similarity	NPC96408
0.8828	High Similarity	NPC321980
0.8828	High Similarity	NPC279650
0.8828	High Similarity	NPC258630
0.8828	High Similarity	NPC470087
0.8819	High Similarity	NPC471697
0.8819	High Similarity	NPC53181
0.8819	High Similarity	NPC472515
0.8819	High Similarity	NPC240305
0.8819	High Similarity	NPC217186
0.8819	High Similarity	NPC37206
0.8819	High Similarity	NPC473209
0.8811	High Similarity	NPC38153
0.8811	High Similarity	NPC332594
0.8811	High Similarity	NPC253616
0.8811	High Similarity	NPC255801
0.8811	High Similarity	NPC322301
0.8808	High Similarity	NPC193200
0.88	High Similarity	NPC204561
0.88	High Similarity	NPC309512
0.88	High Similarity	NPC471677

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 NPC288910 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	931
0.2-0.3	1786
0.3-0.4	2520
0.4-0.5	1977
0.5-0.6	1078
0.6-0.7	365
0.7-0.8	122
0.8-0.85	47
0.85-0.9	9
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8776	High Similarity	NPD4378	Clinical (unspecified phase)
0.8649	High Similarity	NPD2534	Approved
0.8649	High Similarity	NPD2533	Approved
0.8649	High Similarity	NPD2532	Approved
0.8636	High Similarity	NPD7075	Discontinued
0.8562	High Similarity	NPD2800	Approved
0.8562	High Similarity	NPD7096	Clinical (unspecified phase)
0.8531	High Similarity	NPD6651	Approved
0.8506	High Similarity	NPD8443	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD6801	Discontinued
0.8493	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD4380	Phase 2
0.8442	Intermediate Similarity	NPD7819	Suspended
0.8442	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD7411	Suspended
0.8425	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD1549	Phase 2
0.8356	Intermediate Similarity	NPD2796	Approved
0.8333	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5124	Phase 1
0.8311	Intermediate Similarity	NPD1243	Approved
0.8289	Intermediate Similarity	NPD920	Approved
0.8288	Intermediate Similarity	NPD1510	Phase 2
0.828	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD7768	Phase 2
0.8212	Intermediate Similarity	NPD6799	Approved
0.8158	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD1934	Approved
0.8138	Intermediate Similarity	NPD1240	Approved
0.8133	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD3817	Phase 2
0.8027	Intermediate Similarity	NPD1607	Approved
0.8013	Intermediate Similarity	NPD6599	Discontinued
0.8013	Intermediate Similarity	NPD3750	Approved
0.8012	Intermediate Similarity	NPD6959	Discontinued
0.7987	Intermediate Similarity	NPD1551	Phase 2
0.7987	Intermediate Similarity	NPD2935	Discontinued
0.7975	Intermediate Similarity	NPD2801	Approved
0.7974	Intermediate Similarity	NPD1511	Approved
0.7963	Intermediate Similarity	NPD5710	Approved
0.7963	Intermediate Similarity	NPD5711	Approved
0.7939	Intermediate Similarity	NPD7054	Approved
0.7939	Intermediate Similarity	NPD7286	Phase 2
0.7935	Intermediate Similarity	NPD5403	Approved
0.7927	Intermediate Similarity	NPD7473	Discontinued
0.7919	Intermediate Similarity	NPD2799	Discontinued
0.7892	Intermediate Similarity	NPD7074	Phase 3
0.7892	Intermediate Similarity	NPD7472	Approved
0.7879	Intermediate Similarity	NPD3818	Discontinued
0.7877	Intermediate Similarity	NPD2313	Discontinued
0.7875	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1512	Approved
0.7866	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6166	Phase 2
0.7844	Intermediate Similarity	NPD5953	Discontinued
0.7831	Intermediate Similarity	NPD5844	Phase 1
0.7826	Intermediate Similarity	NPD3749	Approved
0.7812	Intermediate Similarity	NPD5402	Approved
0.7806	Intermediate Similarity	NPD5401	Approved
0.7798	Intermediate Similarity	NPD7251	Discontinued
0.7798	Intermediate Similarity	NPD6559	Discontinued
0.7778	Intermediate Similarity	NPD919	Approved
0.7778	Intermediate Similarity	NPD4628	Phase 3
0.7778	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD3882	Suspended
0.7751	Intermediate Similarity	NPD7808	Phase 3
0.7751	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD422	Phase 1
0.7744	Intermediate Similarity	NPD6232	Discontinued
0.774	Intermediate Similarity	NPD6832	Phase 2
0.7738	Intermediate Similarity	NPD6797	Phase 2
0.773	Intermediate Similarity	NPD5494	Approved
0.7692	Intermediate Similarity	NPD9717	Approved
0.7682	Intermediate Similarity	NPD3748	Approved
0.7682	Intermediate Similarity	NPD7033	Discontinued
0.7655	Intermediate Similarity	NPD1203	Approved
0.7635	Intermediate Similarity	NPD3268	Approved
0.7625	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD3226	Approved
0.7582	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6002	Phase 3
0.7582	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6005	Phase 3
0.7582	Intermediate Similarity	NPD6004	Phase 3
0.7534	Intermediate Similarity	NPD2797	Approved
0.7529	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6100	Approved
0.7516	Intermediate Similarity	NPD6099	Approved
0.7514	Intermediate Similarity	NPD4363	Phase 3
0.7514	Intermediate Similarity	NPD4360	Phase 2
0.7483	Intermediate Similarity	NPD230	Phase 1
0.7468	Intermediate Similarity	NPD2346	Discontinued
0.74	Intermediate Similarity	NPD1296	Phase 2
0.74	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1652	Phase 2
0.7368	Intermediate Similarity	NPD447	Suspended
0.7368	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1019	Discontinued
0.7365	Intermediate Similarity	NPD1247	Approved
0.7358	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2344	Approved
0.7343	Intermediate Similarity	NPD9545	Approved
0.7338	Intermediate Similarity	NPD4308	Phase 3
0.7321	Intermediate Similarity	NPD7229	Phase 3
0.7317	Intermediate Similarity	NPD1465	Phase 2
0.7303	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD8312	Approved
0.7299	Intermediate Similarity	NPD8313	Approved
0.7297	Intermediate Similarity	NPD3267	Approved
0.7297	Intermediate Similarity	NPD3266	Approved
0.7285	Intermediate Similarity	NPD411	Approved
0.7284	Intermediate Similarity	NPD7458	Discontinued
0.7284	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4361	Phase 2
0.7278	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4908	Phase 1
0.7261	Intermediate Similarity	NPD2654	Approved
0.7255	Intermediate Similarity	NPD6355	Discontinued
0.7248	Intermediate Similarity	NPD2798	Approved
0.723	Intermediate Similarity	NPD3225	Approved
0.7226	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1608	Approved
0.7203	Intermediate Similarity	NPD9493	Approved
0.7188	Intermediate Similarity	NPD7390	Discontinued
0.7175	Intermediate Similarity	NPD8434	Phase 2
0.7171	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2309	Approved
0.7166	Intermediate Similarity	NPD7584	Approved
0.7152	Intermediate Similarity	NPD37	Approved
0.7151	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1610	Phase 2
0.7126	Intermediate Similarity	NPD4965	Approved
0.7126	Intermediate Similarity	NPD4967	Phase 2
0.7126	Intermediate Similarity	NPD4966	Approved
0.7117	Intermediate Similarity	NPD1653	Approved
0.7108	Intermediate Similarity	NPD8455	Phase 2
0.7103	Intermediate Similarity	NPD1548	Phase 1
0.7099	Intermediate Similarity	NPD6273	Approved
0.7095	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5890	Approved
0.7091	Intermediate Similarity	NPD5889	Approved
0.7089	Intermediate Similarity	NPD2424	Discontinued
0.7078	Intermediate Similarity	NPD4307	Phase 2
0.7078	Intermediate Similarity	NPD943	Approved
0.7069	Intermediate Similarity	NPD1729	Discontinued
0.7066	Intermediate Similarity	NPD5353	Approved
0.7066	Intermediate Similarity	NPD4288	Approved
0.7059	Intermediate Similarity	NPD7199	Phase 2
0.7059	Intermediate Similarity	NPD6798	Discontinued
0.7055	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6234	Discontinued
0.7039	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7585	Approved
0.7035	Intermediate Similarity	NPD2403	Approved
0.7035	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6667	Approved
0.7019	Intermediate Similarity	NPD6666	Approved
0.7007	Intermediate Similarity	NPD17	Approved
0.7006	Intermediate Similarity	NPD5761	Phase 2
0.7006	Intermediate Similarity	NPD5760	Phase 2
0.7	Intermediate Similarity	NPD4287	Approved
0.7	Intermediate Similarity	NPD7003	Approved
0.7	Intermediate Similarity	NPD8151	Discontinued
0.6989	Remote Similarity	NPD6104	Discontinued
0.6984	Remote Similarity	NPD7583	Approved
0.6983	Remote Similarity	NPD8150	Discontinued
0.6977	Remote Similarity	NPD3926	Phase 2
0.6968	Remote Similarity	NPD1613	Approved
0.6968	Remote Similarity	NPD4060	Phase 1
0.6968	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4477	Approved
0.6962	Remote Similarity	NPD4476	Approved
0.6962	Remote Similarity	NPD5408	Approved
0.6962	Remote Similarity	NPD5404	Approved
0.6962	Remote Similarity	NPD5406	Approved
0.6962	Remote Similarity	NPD5405	Approved
0.6954	Remote Similarity	NPD1164	Approved
0.6954	Remote Similarity	NPD7228	Approved
0.6946	Remote Similarity	NPD6844	Discontinued
0.6941	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4749	Approved
0.6928	Remote Similarity	NPD6585	Discontinued
0.6927	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7783	Phase 2
0.6923	Remote Similarity	NPD1933	Approved
0.6915	Remote Similarity	NPD7435	Discontinued
0.6908	Remote Similarity	NPD6917	Clinical (unspecified phase)

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