NPASS Compound

Structure

NPC474738 OpenBabel07101718322D 31 34 0 0 1 0 0 0 0 0999 V2000 0.0850 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0850 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4538 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 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 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 13 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 14 2 0 0 0 0 10 14 1 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 15 19 1 0 0 0 0 16 23 2 0 0 0 0 16 24 1 0 0 0 0 17 25 1 6 0 0 0 17 30 1 0 0 0 0 18 26 2 0 0 0 0 18 31 1 0 0 0 0 19 22 2 0 0 0 0 19 23 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 31 1 0 0 0 0 24 30 1 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.17
Volume:	435.743
LogP:	4.937
LogD:	3.239
LogS:	-3.919
# Rotatable Bonds:	5
TPSA:	96.97
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.465
Synthetic Accessibility Score:	3.76
Fsp3:	0.36
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:	-4.776
MDCK Permeability:	1.9131866793031804e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.095

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	98.67789459228516%
Volume Distribution (VD):	0.437
Pgp-substrate:	1.6080130338668823%

ADMET: Metabolism

CYP1A2-inhibitor:	0.404
CYP1A2-substrate:	0.566
CYP2C19-inhibitor:	0.421
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.844
CYP2C9-substrate:	0.738
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.272
CYP3A4-inhibitor:	0.278
CYP3A4-substrate:	0.295

ADMET: Excretion

Clearance (CL):	3.33
Half-life (T1/2):	0.102

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.7
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.13
Rat Oral Acute Toxicity:	0.732
Maximum Recommended Daily Dose:	0.605
Skin Sensitization:	0.277
Carcinogencity:	0.463
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.392

Download Data

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

Natural Product: NPC474738

Natural Product ID:	NPC474738
*Common Name:**	Mammea A/Ab Cyclo F
IUPAC Name:	(8S)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylbutanoyl)-4-phenyl-8,9-dihydrofuro[2,3-h]chromen-2-one
Synonyms:
Standard InCHIKey:	AVIZABGQXBMRCJ-RUINGEJQSA-N
Standard InCHI:	InChI=1S/C25H26O6/c1-5-13(2)21(27)20-22(28)19-15(14-9-7-6-8-10-14)12-18(26)31-23(19)16-11-17(25(3,4)29)30-24(16)20/h6-10,12-13,17,28-29H,5,11H2,1-4H3/t13?,17-/m0/s1
SMILES:	CCC(C)C(=O)C1=C2C(=C3C(=C1O)C(=CC(=O)O3)C4=CC=CC=C4)CC(O2)C(C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481039
PubChem CID:	44593589
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
NPO27228	Calophyllum dispar	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374944]
NPO33501	marila pluricostata	Species	Calophyllaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15787438]
NPO27228	Calophyllum dispar	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
ED50	1
GI50	3

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	5.0	ug ml-1	PMID[533164]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	3.4	ug.mL-1	PMID[533165]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	4.4	ug.mL-1	PMID[533165]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	4.8	ug.mL-1	PMID[533165]

☑ 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 NPC474738 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	1442
0.2-0.3	3266
0.3-0.4	7500
0.4-0.5	10911
0.5-0.6	4370
0.6-0.7	5365
0.7-0.8	4879
0.8-0.85	3026
0.85-0.9	1320
0.9-0.95	230
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC78554
1.0	High Similarity	NPC321372
1.0	High Similarity	NPC475797
1.0	High Similarity	NPC109967
1.0	High Similarity	NPC469936
1.0	High Similarity	NPC474609
1.0	High Similarity	NPC129053
0.9932	High Similarity	NPC108937
0.9932	High Similarity	NPC279218
0.973	High Similarity	NPC290671
0.9667	High Similarity	NPC469934
0.9597	High Similarity	NPC471675
0.9533	High Similarity	NPC327269
0.9533	High Similarity	NPC31627
0.9533	High Similarity	NPC476238
0.953	High Similarity	NPC327059
0.953	High Similarity	NPC470908
0.953	High Similarity	NPC321387
0.953	High Similarity	NPC474735
0.9481	High Similarity	NPC92589
0.9467	High Similarity	NPC472636
0.9404	High Similarity	NPC285623
0.9404	High Similarity	NPC473996
0.94	High Similarity	NPC472421
0.9392	High Similarity	NPC470322
0.9338	High Similarity	NPC472423
0.9338	High Similarity	NPC474772
0.9338	High Similarity	NPC472580
0.9338	High Similarity	NPC474744
0.9333	High Similarity	NPC104236
0.9333	High Similarity	NPC19238
0.9333	High Similarity	NPC164205
0.9324	High Similarity	NPC196137
0.9324	High Similarity	NPC1886
0.9276	High Similarity	NPC477957
0.9276	High Similarity	NPC256141
0.9272	High Similarity	NPC180351
0.9267	High Similarity	NPC208303
0.9267	High Similarity	NPC168085
0.9267	High Similarity	NPC161864
0.9262	High Similarity	NPC154217
0.9262	High Similarity	NPC181388
0.9257	High Similarity	NPC188632
0.9257	High Similarity	NPC87609
0.9257	High Similarity	NPC470296
0.9257	High Similarity	NPC94794
0.9257	High Similarity	NPC196459
0.9257	High Similarity	NPC112791
0.9216	High Similarity	NPC472583
0.9216	High Similarity	NPC223701
0.9216	High Similarity	NPC7989
0.9216	High Similarity	NPC248793
0.9216	High Similarity	NPC180301
0.9211	High Similarity	NPC263384
0.9211	High Similarity	NPC244577
0.9211	High Similarity	NPC209142
0.9211	High Similarity	NPC471677
0.9211	High Similarity	NPC472422
0.9211	High Similarity	NPC472420
0.9211	High Similarity	NPC312549
0.9211	High Similarity	NPC471676
0.9205	High Similarity	NPC469932
0.9205	High Similarity	NPC317492
0.92	High Similarity	NPC297886
0.92	High Similarity	NPC249942
0.92	High Similarity	NPC202494
0.92	High Similarity	NPC285748
0.92	High Similarity	NPC14875
0.92	High Similarity	NPC140120
0.9195	High Similarity	NPC469953
0.9195	High Similarity	NPC178627
0.9195	High Similarity	NPC469935
0.9189	High Similarity	NPC472344
0.9189	High Similarity	NPC36181
0.9189	High Similarity	NPC470556
0.9177	High Similarity	NPC204088
0.9177	High Similarity	NPC259007
0.9177	High Similarity	NPC329215
0.9167	High Similarity	NPC328102
0.9156	High Similarity	NPC470681
0.9156	High Similarity	NPC259710
0.9156	High Similarity	NPC217706
0.9156	High Similarity	NPC304207
0.9156	High Similarity	NPC207809
0.9156	High Similarity	NPC48579
0.915	High Similarity	NPC150123
0.915	High Similarity	NPC56232
0.915	High Similarity	NPC244583
0.915	High Similarity	NPC475790
0.915	High Similarity	NPC161881
0.915	High Similarity	NPC10807
0.915	High Similarity	NPC217149
0.915	High Similarity	NPC216035
0.9145	High Similarity	NPC105136
0.9145	High Similarity	NPC321896
0.9145	High Similarity	NPC476185
0.9145	High Similarity	NPC476509
0.9139	High Similarity	NPC469933
0.9133	High Similarity	NPC57470
0.9128	High Similarity	NPC307895
0.9128	High Similarity	NPC474939
0.9128	High Similarity	NPC470909
0.9128	High Similarity	NPC96216
0.9128	High Similarity	NPC470553
0.9122	High Similarity	NPC74397
0.9119	High Similarity	NPC323137
0.9114	High Similarity	NPC91288
0.9108	High Similarity	NPC97812
0.9108	High Similarity	NPC14822
0.9097	High Similarity	NPC215917
0.9097	High Similarity	NPC20530
0.9097	High Similarity	NPC10754
0.9091	High Similarity	NPC469405
0.9091	High Similarity	NPC236756
0.9091	High Similarity	NPC311579
0.9085	High Similarity	NPC262038
0.9085	High Similarity	NPC295650
0.9085	High Similarity	NPC254412
0.9085	High Similarity	NPC278476
0.9085	High Similarity	NPC328740
0.9085	High Similarity	NPC319910
0.9085	High Similarity	NPC474023
0.9085	High Similarity	NPC474021
0.9085	High Similarity	NPC477897
0.9085	High Similarity	NPC262039
0.9085	High Similarity	NPC289774
0.9085	High Similarity	NPC209846
0.9079	High Similarity	NPC472628
0.9079	High Similarity	NPC307052
0.9079	High Similarity	NPC164299
0.9079	High Similarity	NPC139966
0.9079	High Similarity	NPC5173
0.9073	High Similarity	NPC51070
0.9073	High Similarity	NPC296998
0.9073	High Similarity	NPC85773
0.9073	High Similarity	NPC474108
0.9073	High Similarity	NPC473077
0.9073	High Similarity	NPC177995
0.9073	High Similarity	NPC472627
0.9073	High Similarity	NPC180477
0.9073	High Similarity	NPC47388
0.9073	High Similarity	NPC473133
0.9073	High Similarity	NPC222298
0.9073	High Similarity	NPC470670
0.9068	High Similarity	NPC120220
0.9067	High Similarity	NPC470554
0.9067	High Similarity	NPC131568
0.9067	High Similarity	NPC297788
0.9067	High Similarity	NPC133060
0.9067	High Similarity	NPC224714
0.9067	High Similarity	NPC131579
0.9067	High Similarity	NPC294365
0.9067	High Similarity	NPC288910
0.9067	High Similarity	NPC118059
0.906	High Similarity	NPC294432
0.906	High Similarity	NPC130206
0.906	High Similarity	NPC112829
0.9045	High Similarity	NPC49009
0.9045	High Similarity	NPC95472
0.9045	High Similarity	NPC169
0.9045	High Similarity	NPC472624
0.9045	High Similarity	NPC239270
0.9045	High Similarity	NPC303210
0.9038	High Similarity	NPC108456
0.9038	High Similarity	NPC210048
0.9032	High Similarity	NPC111341
0.9032	High Similarity	NPC473241
0.9032	High Similarity	NPC304745
0.9032	High Similarity	NPC476169
0.9032	High Similarity	NPC477958
0.9026	High Similarity	NPC243171
0.9026	High Similarity	NPC210597
0.9026	High Similarity	NPC171651
0.9026	High Similarity	NPC35567
0.9026	High Similarity	NPC138288
0.902	High Similarity	NPC471115
0.902	High Similarity	NPC472633
0.902	High Similarity	NPC29777
0.902	High Similarity	NPC61258
0.9013	High Similarity	NPC10097
0.9013	High Similarity	NPC472345
0.9012	High Similarity	NPC472584
0.9007	High Similarity	NPC20488
0.9007	High Similarity	NPC83357
0.9007	High Similarity	NPC88964
0.9007	High Similarity	NPC195621
0.9007	High Similarity	NPC267375
0.9007	High Similarity	NPC214774
0.9007	High Similarity	NPC54577
0.9007	High Similarity	NPC111786
0.9007	High Similarity	NPC301276
0.9007	High Similarity	NPC470647
0.9007	High Similarity	NPC470910
0.9007	High Similarity	NPC312973
0.9007	High Similarity	NPC472629
0.9007	High Similarity	NPC127059
0.9007	High Similarity	NPC475052
0.9007	High Similarity	NPC67805
0.9007	High Similarity	NPC474161
0.9007	High Similarity	NPC124729

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 NPC474738 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	321
0.1-0.2	869
0.2-0.3	1671
0.3-0.4	2546
0.4-0.5	2022
0.5-0.6	1101
0.6-0.7	408
0.7-0.8	141
0.8-0.85	56
0.85-0.9	13
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9038	High Similarity	NPD7075	Discontinued
0.8968	High Similarity	NPD7096	Clinical (unspecified phase)
0.894	High Similarity	NPD4378	Clinical (unspecified phase)
0.8903	High Similarity	NPD6801	Discontinued
0.8896	High Similarity	NPD4380	Phase 2
0.8846	High Similarity	NPD2393	Clinical (unspecified phase)
0.8693	High Similarity	NPD7410	Clinical (unspecified phase)
0.8679	High Similarity	NPD4381	Clinical (unspecified phase)
0.8662	High Similarity	NPD1934	Approved
0.8627	High Similarity	NPD6799	Approved
0.86	High Similarity	NPD1550	Clinical (unspecified phase)
0.86	High Similarity	NPD1552	Clinical (unspecified phase)
0.8599	High Similarity	NPD7411	Suspended
0.8553	High Similarity	NPD8443	Clinical (unspecified phase)
0.8553	High Similarity	NPD3817	Phase 2
0.8545	High Similarity	NPD7804	Clinical (unspecified phase)
0.8543	High Similarity	NPD1549	Phase 2
0.8533	High Similarity	NPD2796	Approved
0.8491	Intermediate Similarity	NPD7819	Suspended
0.8491	Intermediate Similarity	NPD2801	Approved
0.8485	Intermediate Similarity	NPD3818	Discontinued
0.8467	Intermediate Similarity	NPD1510	Phase 2
0.8462	Intermediate Similarity	NPD920	Approved
0.8418	Intermediate Similarity	NPD6599	Discontinued
0.8393	Intermediate Similarity	NPD6559	Discontinued
0.8387	Intermediate Similarity	NPD1511	Approved
0.8385	Intermediate Similarity	NPD3882	Suspended
0.8366	Intermediate Similarity	NPD1243	Approved
0.8344	Intermediate Similarity	NPD5494	Approved
0.8344	Intermediate Similarity	NPD5403	Approved
0.8333	Intermediate Similarity	NPD2532	Approved
0.8333	Intermediate Similarity	NPD3749	Approved
0.8333	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2533	Approved
0.8333	Intermediate Similarity	NPD2534	Approved
0.8323	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD1512	Approved
0.8272	Intermediate Similarity	NPD7768	Phase 2
0.8272	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD6166	Phase 2
0.8253	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD2800	Approved
0.8247	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD5401	Approved
0.8214	Intermediate Similarity	NPD7054	Approved
0.821	Intermediate Similarity	NPD5402	Approved
0.8204	Intermediate Similarity	NPD7473	Discontinued
0.82	Intermediate Similarity	NPD1240	Approved
0.8194	Intermediate Similarity	NPD3750	Approved
0.8182	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD919	Approved
0.8166	Intermediate Similarity	NPD7074	Phase 3
0.8166	Intermediate Similarity	NPD7472	Approved
0.8133	Intermediate Similarity	NPD6232	Discontinued
0.8129	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD6797	Phase 2
0.8107	Intermediate Similarity	NPD5844	Phase 1
0.8092	Intermediate Similarity	NPD1607	Approved
0.8077	Intermediate Similarity	NPD4628	Phase 3
0.8072	Intermediate Similarity	NPD6959	Discontinued
0.807	Intermediate Similarity	NPD7251	Discontinued
0.8067	Intermediate Similarity	NPD2313	Discontinued
0.8067	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD2935	Discontinued
0.8052	Intermediate Similarity	NPD1551	Phase 2
0.8026	Intermediate Similarity	NPD5124	Phase 1
0.8026	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7808	Phase 3
0.7987	Intermediate Similarity	NPD7033	Discontinued
0.7987	Intermediate Similarity	NPD2799	Discontinued
0.7907	Intermediate Similarity	NPD5953	Discontinued
0.7895	Intermediate Similarity	NPD7286	Phase 2
0.7871	Intermediate Similarity	NPD3748	Approved
0.7857	Intermediate Similarity	NPD6651	Approved
0.7848	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD3268	Approved
0.7803	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3226	Approved
0.779	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD1247	Approved
0.774	Intermediate Similarity	NPD8434	Phase 2
0.7733	Intermediate Similarity	NPD2797	Approved
0.7733	Intermediate Similarity	NPD1203	Approved
0.7711	Intermediate Similarity	NPD1465	Phase 2
0.7706	Intermediate Similarity	NPD5711	Approved
0.7706	Intermediate Similarity	NPD5710	Approved
0.7697	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6832	Phase 2
0.7677	Intermediate Similarity	NPD6355	Discontinued
0.7669	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2346	Discontinued
0.7658	Intermediate Similarity	NPD2344	Approved
0.7658	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7199	Phase 2
0.7643	Intermediate Similarity	NPD4308	Phase 3
0.7633	Intermediate Similarity	NPD6234	Discontinued
0.7625	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7229	Phase 3
0.7597	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6798	Discontinued
0.7584	Intermediate Similarity	NPD422	Phase 1
0.7582	Intermediate Similarity	NPD4363	Phase 3
0.7582	Intermediate Similarity	NPD4360	Phase 2
0.7576	Intermediate Similarity	NPD7458	Discontinued
0.7571	Intermediate Similarity	NPD8313	Approved
0.7571	Intermediate Similarity	NPD8312	Approved
0.7562	Intermediate Similarity	NPD1652	Phase 2
0.7558	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6004	Phase 3
0.7547	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6005	Phase 3
0.7547	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6002	Phase 3
0.7546	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD37	Approved
0.7541	Intermediate Similarity	NPD4361	Phase 2
0.7541	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD9717	Approved
0.7515	Intermediate Similarity	NPD4967	Phase 2
0.7515	Intermediate Similarity	NPD4966	Approved
0.7515	Intermediate Similarity	NPD4965	Approved
0.7513	Intermediate Similarity	NPD7584	Approved
0.75	Intermediate Similarity	NPD3267	Approved
0.75	Intermediate Similarity	NPD3266	Approved
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6100	Approved
0.7484	Intermediate Similarity	NPD6099	Approved
0.7469	Intermediate Similarity	NPD2309	Approved
0.7468	Intermediate Similarity	NPD4908	Phase 1
0.7459	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD4287	Approved
0.7457	Intermediate Similarity	NPD3926	Phase 2
0.7452	Intermediate Similarity	NPD447	Suspended
0.7452	Intermediate Similarity	NPD230	Phase 1
0.7452	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2798	Approved
0.7436	Intermediate Similarity	NPD6233	Phase 2
0.7434	Intermediate Similarity	NPD3225	Approved
0.7396	Intermediate Similarity	NPD8455	Phase 2
0.7394	Intermediate Similarity	NPD5049	Phase 3
0.7391	Intermediate Similarity	NPD2424	Discontinued
0.7389	Intermediate Similarity	NPD4307	Phase 2
0.7389	Intermediate Similarity	NPD943	Approved
0.7389	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1613	Approved
0.7389	Intermediate Similarity	NPD4060	Phase 1
0.7382	Intermediate Similarity	NPD7585	Approved
0.7372	Intermediate Similarity	NPD3764	Approved
0.7365	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1610	Phase 2
0.7351	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD8150	Discontinued
0.7342	Intermediate Similarity	NPD1933	Approved
0.733	Intermediate Similarity	NPD7228	Approved
0.733	Intermediate Similarity	NPD3751	Discontinued
0.733	Intermediate Similarity	NPD7583	Approved
0.733	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1548	Phase 1
0.7314	Intermediate Similarity	NPD2403	Approved
0.7314	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1653	Approved
0.7303	Intermediate Similarity	NPD1608	Approved
0.7299	Intermediate Similarity	NPD3787	Discontinued
0.7289	Intermediate Similarity	NPD6273	Approved
0.7278	Intermediate Similarity	NPD5890	Approved
0.7278	Intermediate Similarity	NPD5889	Approved
0.7273	Intermediate Similarity	NPD7390	Discontinued
0.7268	Intermediate Similarity	NPD7783	Phase 2
0.7268	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7685	Pre-registration
0.7263	Intermediate Similarity	NPD7435	Discontinued
0.7261	Intermediate Similarity	NPD1296	Phase 2
0.7261	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3887	Approved
0.7256	Intermediate Similarity	NPD2354	Approved
0.7256	Intermediate Similarity	NPD6190	Approved
0.7251	Intermediate Similarity	NPD4288	Approved
0.7247	Intermediate Similarity	NPD1729	Discontinued
0.7244	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2654	Approved
0.7226	Intermediate Similarity	NPD1019	Discontinued
0.7219	Intermediate Similarity	NPD6585	Discontinued
0.72	Intermediate Similarity	NPD9545	Approved
0.7197	Intermediate Similarity	NPD3027	Phase 3
0.7196	Intermediate Similarity	NPD6778	Approved
0.7196	Intermediate Similarity	NPD6779	Approved
0.7196	Intermediate Similarity	NPD6777	Approved
0.7196	Intermediate Similarity	NPD6776	Approved
0.7196	Intermediate Similarity	NPD6782	Approved
0.7196	Intermediate Similarity	NPD6780	Approved
0.7196	Intermediate Similarity	NPD6781	Approved
0.7195	Intermediate Similarity	NPD7003	Approved
0.7193	Intermediate Similarity	NPD5760	Phase 2
0.7193	Intermediate Similarity	NPD5761	Phase 2

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