NPASS Compound

Structure

NPC218300 OpenBabel07101718242D 30 34 0 0 1 0 0 0 0 0999 V2000 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.8660 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 2.5981 -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 0.8660 -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 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 2 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 2 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 0.0000 -2.0000 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 -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 -3.4641 -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 -2.0000 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 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 15 2 0 0 0 0 9 15 1 0 0 0 0 10 11 2 0 0 0 0 10 16 1 0 0 0 0 11 25 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 1 1 6 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 2 1 1 0 0 0 14 28 1 0 0 0 0 15 17 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 17 19 1 0 0 0 0 18 26 2 0 0 0 0 18 29 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 20 24 2 0 0 0 0 21 27 2 0 0 0 0 22 28 1 0 0 0 0 23 30 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.15
Volume:	415.76
LogP:	5.717
LogD:	4.358
LogS:	-6.413
# Rotatable Bonds:	1
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.521
Synthetic Accessibility Score:	3.765
Fsp3:	0.28
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.628
MDCK Permeability:	1.7330021364614367e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.212

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	96.78743743896484%
Volume Distribution (VD):	0.465
Pgp-substrate:	2.053591728210449%

ADMET: Metabolism

CYP1A2-inhibitor:	0.666
CYP1A2-substrate:	0.569
CYP2C19-inhibitor:	0.897
CYP2C19-substrate:	0.116
CYP2C9-inhibitor:	0.924
CYP2C9-substrate:	0.719
CYP2D6-inhibitor:	0.503
CYP2D6-substrate:	0.211
CYP3A4-inhibitor:	0.682
CYP3A4-substrate:	0.289

ADMET: Excretion

Clearance (CL):	1.85
Half-life (T1/2):	0.073

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.91
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.937
Maximum Recommended Daily Dose:	0.538
Skin Sensitization:	0.231
Carcinogencity:	0.839
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.515

Download Data

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

Natural Product: NPC218300

Natural Product ID:	NPC218300
*Common Name:**	YRHQANFINIANSK-ZIAGYGMSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YRHQANFINIANSK-ZIAGYGMSSA-N
Standard InCHI:	InChI=1S/C25H22O5/c1-13-14(2)28-22-16-10-11-25(3,4)30-23(16)19-17(15-8-6-5-7-9-15)12-18(26)29-24(19)20(22)21(13)27/h5-14H,1-4H3/t13-,14-/m1/s1
SMILES:	C[C@H]1Oc2c3C=CC(Oc3c3c(c2C(=O)[C@@H]1C)oc(=O)cc3c1ccccc1)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL334946
PubChem CID:	455252
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0003650] Prenylated neoflavonoids

*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
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15678383]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16045947]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[20188156]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	Malaysian	n.a.	PMID[7506311]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2804	Calophyllum inophyllum	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	3
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	10000.0	nM	PMID[494235]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	18000.0	nM	PMID[494235]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	8300.0	nM	PMID[494236]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	35300.0	nM	PMID[494236]

☑ 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 NPC218300 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	436
0.1-0.2	1710
0.2-0.3	4035
0.3-0.4	9899
0.4-0.5	9017
0.5-0.6	4389
0.6-0.7	6054
0.7-0.8	5231
0.8-0.85	1376
0.85-0.9	425
0.9-0.95	110
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC282335
0.9643	High Similarity	NPC201820
0.9643	High Similarity	NPC52576
0.9507	High Similarity	NPC59522
0.9448	High Similarity	NPC104236
0.9448	High Similarity	NPC164205
0.9448	High Similarity	NPC19238
0.9362	High Similarity	NPC473209
0.9315	High Similarity	NPC164299
0.931	High Similarity	NPC249942
0.931	High Similarity	NPC297886
0.9296	High Similarity	NPC472409
0.9291	High Similarity	NPC17848
0.9247	High Similarity	NPC469933
0.9247	High Similarity	NPC161191
0.9247	High Similarity	NPC208303
0.9247	High Similarity	NPC161864
0.9241	High Similarity	NPC57470
0.9225	High Similarity	NPC11566
0.922	High Similarity	NPC259685
0.922	High Similarity	NPC38153
0.9189	High Similarity	NPC209142
0.9189	High Similarity	NPC312549
0.9184	High Similarity	NPC469932
0.9178	High Similarity	NPC140120
0.9178	High Similarity	NPC180477
0.9172	High Similarity	NPC294365
0.9172	High Similarity	NPC179970
0.9149	High Similarity	NPC161196
0.9122	High Similarity	NPC474735
0.9122	High Similarity	NPC151973
0.9116	High Similarity	NPC321623
0.9116	High Similarity	NPC189087
0.911	High Similarity	NPC195621
0.911	High Similarity	NPC267375
0.911	High Similarity	NPC88964
0.911	High Similarity	NPC176229
0.911	High Similarity	NPC111786
0.911	High Similarity	NPC474161
0.911	High Similarity	NPC476088
0.911	High Similarity	NPC83357
0.911	High Similarity	NPC142405
0.911	High Similarity	NPC470322
0.911	High Similarity	NPC54577
0.911	High Similarity	NPC301276
0.911	High Similarity	NPC67805
0.911	High Similarity	NPC246948
0.911	High Similarity	NPC475052
0.911	High Similarity	NPC312973
0.911	High Similarity	NPC214774
0.911	High Similarity	NPC470647
0.911	High Similarity	NPC20488
0.9103	High Similarity	NPC87609
0.9103	High Similarity	NPC112791
0.9103	High Similarity	NPC196459
0.9103	High Similarity	NPC188632
0.9103	High Similarity	NPC470296
0.9103	High Similarity	NPC94794
0.9091	High Similarity	NPC136095
0.9085	High Similarity	NPC157855
0.9085	High Similarity	NPC253616
0.9078	High Similarity	NPC46869
0.9078	High Similarity	NPC99854
0.906	High Similarity	NPC290671
0.9048	High Similarity	NPC110303
0.9048	High Similarity	NPC473077
0.9048	High Similarity	NPC283234
0.9048	High Similarity	NPC296998
0.9048	High Similarity	NPC23728
0.9041	High Similarity	NPC469935
0.9041	High Similarity	NPC131579
0.9041	High Similarity	NPC319752
0.9041	High Similarity	NPC131568
0.9041	High Similarity	NPC1886
0.9041	High Similarity	NPC178627
0.9041	High Similarity	NPC469953
0.9041	High Similarity	NPC196137
0.9041	High Similarity	NPC171656
0.9034	High Similarity	NPC36181
0.9034	High Similarity	NPC147145
0.9021	High Similarity	NPC36414
0.9014	High Similarity	NPC268081
0.9	High Similarity	NPC469952
0.9	High Similarity	NPC469955
0.8986	High Similarity	NPC160821
0.8986	High Similarity	NPC132592
0.898	High Similarity	NPC285630
0.898	High Similarity	NPC127059
0.898	High Similarity	NPC154217
0.898	High Similarity	NPC181388
0.8973	High Similarity	NPC223812
0.8973	High Similarity	NPC77794
0.8973	High Similarity	NPC278249
0.8973	High Similarity	NPC478086
0.8973	High Similarity	NPC107177
0.8973	High Similarity	NPC85162
0.8973	High Similarity	NPC125894
0.8973	High Similarity	NPC214166
0.8973	High Similarity	NPC316816
0.8973	High Similarity	NPC81697
0.8966	High Similarity	NPC110038
0.8966	High Similarity	NPC470555
0.8966	High Similarity	NPC22467
0.8966	High Similarity	NPC248372
0.8958	High Similarity	NPC472515
0.8951	High Similarity	NPC103001
0.8947	High Similarity	NPC475797
0.8947	High Similarity	NPC78554
0.8947	High Similarity	NPC109967
0.8947	High Similarity	NPC321372
0.8947	High Similarity	NPC469936
0.8947	High Similarity	NPC474609
0.8947	High Similarity	NPC474738
0.8947	High Similarity	NPC129053
0.894	High Similarity	NPC88983
0.8933	High Similarity	NPC78835
0.8933	High Similarity	NPC204561
0.8933	High Similarity	NPC317715
0.8933	High Similarity	NPC316960
0.8933	High Similarity	NPC309512
0.8933	High Similarity	NPC148945
0.8926	High Similarity	NPC5173
0.8926	High Similarity	NPC473016
0.8919	High Similarity	NPC24673
0.8919	High Similarity	NPC177995
0.8919	High Similarity	NPC201731
0.8919	High Similarity	NPC97716
0.8919	High Similarity	NPC104406
0.8919	High Similarity	NPC237635
0.8919	High Similarity	NPC79469
0.8919	High Similarity	NPC474108
0.8919	High Similarity	NPC285748
0.8912	High Similarity	NPC235217
0.8912	High Similarity	NPC473015
0.8912	High Similarity	NPC473013
0.8912	High Similarity	NPC209040
0.8912	High Similarity	NPC473014
0.8904	High Similarity	NPC148757
0.8904	High Similarity	NPC32739
0.8904	High Similarity	NPC265040
0.8904	High Similarity	NPC40833
0.8904	High Similarity	NPC76372
0.8904	High Similarity	NPC296917
0.8904	High Similarity	NPC37496
0.8904	High Similarity	NPC62840
0.8904	High Similarity	NPC306829
0.8904	High Similarity	NPC324134
0.8904	High Similarity	NPC10937
0.8904	High Similarity	NPC76338
0.8904	High Similarity	NPC293852
0.8904	High Similarity	NPC227579
0.8904	High Similarity	NPC328164
0.8904	High Similarity	NPC324436
0.8904	High Similarity	NPC125855
0.8904	High Similarity	NPC223500
0.8904	High Similarity	NPC59739
0.8904	High Similarity	NPC167624
0.8904	High Similarity	NPC107572
0.8904	High Similarity	NPC78
0.8904	High Similarity	NPC166482
0.8904	High Similarity	NPC220998
0.8904	High Similarity	NPC299080
0.8904	High Similarity	NPC194432
0.8904	High Similarity	NPC177354
0.8904	High Similarity	NPC66515
0.8904	High Similarity	NPC1089
0.8904	High Similarity	NPC228504
0.8904	High Similarity	NPC214236
0.8904	High Similarity	NPC78803
0.8904	High Similarity	NPC182852
0.8904	High Similarity	NPC64915
0.8904	High Similarity	NPC217083
0.8904	High Similarity	NPC161506
0.8904	High Similarity	NPC166934
0.8897	High Similarity	NPC221173
0.8897	High Similarity	NPC150522
0.8882	High Similarity	NPC108937
0.8882	High Similarity	NPC477530
0.8882	High Similarity	NPC279218
0.8881	High Similarity	NPC254741
0.8873	High Similarity	NPC125269
0.8867	High Similarity	NPC472633
0.8867	High Similarity	NPC29777
0.8867	High Similarity	NPC471115
0.8865	High Similarity	NPC473655
0.8865	High Similarity	NPC101294
0.8859	High Similarity	NPC266572
0.8859	High Similarity	NPC6511
0.8851	High Similarity	NPC470131
0.8851	High Similarity	NPC470133
0.8851	High Similarity	NPC470134
0.8851	High Similarity	NPC109183
0.8851	High Similarity	NPC473078
0.8851	High Similarity	NPC470132
0.8851	High Similarity	NPC228779
0.8844	High Similarity	NPC39329
0.8844	High Similarity	NPC164980
0.8844	High Similarity	NPC143896
0.8844	High Similarity	NPC75049
0.8844	High Similarity	NPC175504

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 NPC218300 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	965
0.2-0.3	1619
0.3-0.4	2681
0.4-0.5	1980
0.5-0.6	1056
0.6-0.7	310
0.7-0.8	112
0.8-0.85	34
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8881	High Similarity	NPD2796	Approved
0.8808	High Similarity	NPD7411	Suspended
0.8693	High Similarity	NPD7096	Clinical (unspecified phase)
0.8658	High Similarity	NPD7410	Clinical (unspecified phase)
0.8627	High Similarity	NPD6801	Discontinued
0.8571	High Similarity	NPD7819	Suspended
0.8562	High Similarity	NPD1550	Clinical (unspecified phase)
0.8562	High Similarity	NPD1552	Clinical (unspecified phase)
0.8533	High Similarity	NPD4378	Clinical (unspecified phase)
0.8526	High Similarity	NPD7075	Discontinued
0.8516	High Similarity	NPD8443	Clinical (unspecified phase)
0.8503	High Similarity	NPD1549	Phase 2
0.8467	Intermediate Similarity	NPD6799	Approved
0.8446	Intermediate Similarity	NPD1243	Approved
0.8421	Intermediate Similarity	NPD920	Approved
0.84	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD4380	Phase 2
0.8345	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD5124	Phase 1
0.8333	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD5494	Approved
0.8301	Intermediate Similarity	NPD5403	Approved
0.8299	Intermediate Similarity	NPD3748	Approved
0.8289	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD5401	Approved
0.8258	Intermediate Similarity	NPD6599	Discontinued
0.82	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1510	Phase 2
0.8171	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD3817	Phase 2
0.8138	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6832	Phase 2
0.8113	Intermediate Similarity	NPD7768	Phase 2
0.8063	Intermediate Similarity	NPD3749	Approved
0.8038	Intermediate Similarity	NPD1934	Approved
0.8027	Intermediate Similarity	NPD1240	Approved
0.8026	Intermediate Similarity	NPD3750	Approved
0.8025	Intermediate Similarity	NPD6959	Discontinued
0.8012	Intermediate Similarity	NPD919	Approved
0.7937	Intermediate Similarity	NPD5402	Approved
0.7933	Intermediate Similarity	NPD2799	Discontinued
0.7919	Intermediate Similarity	NPD1607	Approved
0.7917	Intermediate Similarity	NPD3267	Approved
0.7917	Intermediate Similarity	NPD3266	Approved
0.7895	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD2313	Discontinued
0.7887	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6166	Phase 2
0.7879	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD5890	Approved
0.7862	Intermediate Similarity	NPD5889	Approved
0.7844	Intermediate Similarity	NPD5844	Phase 1
0.7844	Intermediate Similarity	NPD7054	Approved
0.7815	Intermediate Similarity	NPD7033	Discontinued
0.7799	Intermediate Similarity	NPD6585	Discontinued
0.7798	Intermediate Similarity	NPD7472	Approved
0.7798	Intermediate Similarity	NPD7074	Phase 3
0.7778	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD3268	Approved
0.7764	Intermediate Similarity	NPD2801	Approved
0.7763	Intermediate Similarity	NPD1551	Phase 2
0.7756	Intermediate Similarity	NPD1511	Approved
0.7751	Intermediate Similarity	NPD6797	Phase 2
0.7707	Intermediate Similarity	NPD2533	Approved
0.7707	Intermediate Similarity	NPD2534	Approved
0.7707	Intermediate Similarity	NPD2532	Approved
0.7706	Intermediate Similarity	NPD7251	Discontinued
0.7682	Intermediate Similarity	NPD6651	Approved
0.7671	Intermediate Similarity	NPD2797	Approved
0.7667	Intermediate Similarity	NPD4307	Phase 2
0.7665	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7808	Phase 3
0.7661	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1512	Approved
0.7651	Intermediate Similarity	NPD1296	Phase 2
0.7647	Intermediate Similarity	NPD5953	Discontinued
0.7647	Intermediate Similarity	NPD2935	Discontinued
0.764	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7286	Phase 2
0.7619	Intermediate Similarity	NPD7473	Discontinued
0.7616	Intermediate Similarity	NPD1933	Approved
0.7616	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD2800	Approved
0.7603	Intermediate Similarity	NPD3225	Approved
0.7602	Intermediate Similarity	NPD6559	Discontinued
0.7597	Intermediate Similarity	NPD2346	Discontinued
0.7574	Intermediate Similarity	NPD3818	Discontinued
0.7564	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4628	Phase 3
0.7561	Intermediate Similarity	NPD3882	Suspended
0.7558	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1203	Approved
0.7545	Intermediate Similarity	NPD6232	Discontinued
0.7533	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD1019	Discontinued
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1247	Approved
0.7484	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4308	Phase 3
0.7466	Intermediate Similarity	NPD9717	Approved
0.7452	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD4360	Phase 2
0.743	Intermediate Similarity	NPD4363	Phase 3
0.7407	Intermediate Similarity	NPD7458	Discontinued
0.7407	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD3887	Approved
0.74	Intermediate Similarity	NPD4908	Phase 1
0.7397	Intermediate Similarity	NPD422	Phase 1
0.7389	Intermediate Similarity	NPD2654	Approved
0.7379	Intermediate Similarity	NPD17	Approved
0.7368	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6100	Approved
0.7308	Intermediate Similarity	NPD6099	Approved
0.7303	Intermediate Similarity	NPD6798	Discontinued
0.7294	Intermediate Similarity	NPD3926	Phase 2
0.7289	Intermediate Similarity	NPD4288	Approved
0.7285	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1652	Phase 2
0.7268	Intermediate Similarity	NPD8285	Discontinued
0.7261	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5710	Approved
0.7235	Intermediate Similarity	NPD7229	Phase 3
0.7235	Intermediate Similarity	NPD5711	Approved
0.7233	Intermediate Similarity	NPD7003	Approved
0.723	Intermediate Similarity	NPD1608	Approved
0.723	Intermediate Similarity	NPD3972	Approved
0.7229	Intermediate Similarity	NPD8455	Phase 2
0.7229	Intermediate Similarity	NPD1465	Phase 2
0.7222	Intermediate Similarity	NPD6273	Approved
0.7216	Intermediate Similarity	NPD8312	Approved
0.7216	Intermediate Similarity	NPD8313	Approved
0.7207	Intermediate Similarity	NPD4287	Approved
0.7188	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD5535	Approved
0.7179	Intermediate Similarity	NPD7097	Phase 1
0.7162	Intermediate Similarity	NPD1610	Phase 2
0.7161	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD2344	Approved
0.7152	Intermediate Similarity	NPD2353	Approved
0.7152	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3787	Discontinued
0.7135	Intermediate Similarity	NPD6808	Phase 2
0.7133	Intermediate Similarity	NPD1241	Discontinued
0.7123	Intermediate Similarity	NPD1548	Phase 1
0.7117	Intermediate Similarity	NPD5049	Phase 3
0.7104	Intermediate Similarity	NPD4361	Phase 2
0.7104	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7390	Discontinued
0.709	Intermediate Similarity	NPD7584	Approved
0.7076	Intermediate Similarity	NPD7199	Phase 2
0.7069	Intermediate Similarity	NPD3751	Discontinued
0.7052	Intermediate Similarity	NPD2403	Approved
0.7051	Intermediate Similarity	NPD4622	Approved
0.7051	Intermediate Similarity	NPD4618	Approved
0.7044	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6002	Phase 3
0.7044	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6005	Phase 3
0.7044	Intermediate Similarity	NPD6004	Phase 3
0.7032	Intermediate Similarity	NPD6233	Phase 2
0.7025	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1894	Discontinued
0.7007	Intermediate Similarity	NPD9545	Approved
0.7	Intermediate Similarity	NPD8434	Phase 2
0.7	Intermediate Similarity	NPD8150	Discontinued
0.7	Intermediate Similarity	NPD7583	Approved
0.6994	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD3140	Approved
0.6987	Remote Similarity	NPD2979	Phase 3
0.6987	Remote Similarity	NPD3142	Approved
0.6982	Remote Similarity	NPD5353	Approved
0.6981	Remote Similarity	NPD4477	Approved
0.6981	Remote Similarity	NPD2438	Suspended
0.6981	Remote Similarity	NPD5404	Approved
0.6981	Remote Similarity	NPD5405	Approved
0.6981	Remote Similarity	NPD5406	Approved
0.6981	Remote Similarity	NPD4476	Approved
0.6981	Remote Similarity	NPD5408	Approved
0.6975	Remote Similarity	NPD2354	Approved
0.6975	Remote Similarity	NPD2309	Approved
0.6968	Remote Similarity	NPD411	Approved
0.6964	Remote Similarity	NPD6844	Discontinued
0.6963	Remote Similarity	NPD7585	Approved
0.6962	Remote Similarity	NPD5688	Approved
0.6962	Remote Similarity	NPD5689	Approved
0.6959	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD447	Suspended
0.6943	Remote Similarity	NPD7783	Phase 2
0.6943	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6937	Remote 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