NPASS Compound

Structure

CID323137 OpenBabel06191716172D 32 35 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 -3.0878 1.6750 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 1 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 0 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 6 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 30 1 0 0 0 0 6 14 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 15 2 0 0 0 0 11 15 1 0 0 0 0 12 17 1 0 0 0 0 12 18 2 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 2 1 6 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 16 20 1 0 0 0 0 17 24 2 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 18 31 1 0 0 0 0 19 27 2 0 0 0 0 19 32 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 21 25 2 0 0 0 0 22 28 2 0 0 0 0 23 29 1 0 0 0 0 24 32 1 0 0 0 0 25 31 1 0 0 0 0 26 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.17
Volume:	450.403
LogP:	5.63
LogD:	3.684
LogS:	-5.982
# Rotatable Bonds:	6
TPSA:	89.88
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.295
Synthetic Accessibility Score:	3.543
Fsp3:	0.308
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:	-4.786
MDCK Permeability:	2.284724178025499e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	94.32837677001953%
Volume Distribution (VD):	0.484
Pgp-substrate:	3.639478921890259%

ADMET: Metabolism

CYP1A2-inhibitor:	0.738
CYP1A2-substrate:	0.943
CYP2C19-inhibitor:	0.753
CYP2C19-substrate:	0.103
CYP2C9-inhibitor:	0.887
CYP2C9-substrate:	0.594
CYP2D6-inhibitor:	0.073
CYP2D6-substrate:	0.427
CYP3A4-inhibitor:	0.27
CYP3A4-substrate:	0.481

ADMET: Excretion

Clearance (CL):	4.496
Half-life (T1/2):	0.079

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.93
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.382
Rat Oral Acute Toxicity:	0.777
Maximum Recommended Daily Dose:	0.321
Skin Sensitization:	0.271
Carcinogencity:	0.537
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.542

Download Data

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

Natural Product: NPC323137

Natural Product ID:	NPC323137
*Common Name:**	Ochrocarpin D
IUPAC Name:	5-hydroxy-8-(2-methoxypropan-2-yl)-6-[(2S)-2-methylbutanoyl]-4-phenylfuro[2,3-h]chromen-2-one
Synonyms:	Ochrocarpin D
Standard InCHIKey:	PSBCHGQXBPONOM-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C26H26O6/c1-6-14(2)22(28)21-23(29)20-16(15-10-8-7-9-11-15)13-19(27)32-24(20)17-12-18(31-25(17)21)26(3,4)30-5/h7-14,29H,6H2,1-5H3/t14-/m0/s1
SMILES:	CCC(C)C(=O)C1=C2C(=C3C(=C1O)C(=CC(=O)O3)C4=CC=CC=C4)C=C(O2)C(C)(C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487416
PubChem CID:	44559858
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0001389] Neoflavones

*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
NPO369	Ochrocarpos punctatus	Species	Clusiaceae	Eukaryota	n.a.	bark	n.a.	PMID[12141854]
NPO369	Ochrocarpos punctatus	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	6.3	ug.mL-1	PMID[454272]

☑ 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 NPC323137 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	389
0.1-0.2	1628
0.2-0.3	3843
0.3-0.4	8855
0.4-0.5	9678
0.5-0.6	4380
0.6-0.7	5744
0.7-0.8	4684
0.8-0.85	2650
0.85-0.9	776
0.9-0.95	66
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9809	High Similarity	NPC259007
0.9809	High Similarity	NPC204088
0.9809	High Similarity	NPC329215
0.9313	High Similarity	NPC219861
0.9308	High Similarity	NPC260296
0.9308	High Similarity	NPC115432
0.9255	High Similarity	NPC155640
0.9245	High Similarity	NPC244750
0.9207	High Similarity	NPC120220
0.9152	High Similarity	NPC472584
0.9136	High Similarity	NPC472581
0.9119	High Similarity	NPC469936
0.9119	High Similarity	NPC474609
0.9119	High Similarity	NPC129053
0.9119	High Similarity	NPC474738
0.9119	High Similarity	NPC109967
0.9119	High Similarity	NPC321372
0.9119	High Similarity	NPC475797
0.9119	High Similarity	NPC78554
0.9114	High Similarity	NPC472462
0.9103	High Similarity	NPC37208
0.9103	High Similarity	NPC226644
0.9103	High Similarity	NPC37226
0.9103	High Similarity	NPC221868
0.9085	High Similarity	NPC476459
0.9062	High Similarity	NPC65504
0.9057	High Similarity	NPC108937
0.9057	High Similarity	NPC279218
0.9057	High Similarity	NPC469934
0.9038	High Similarity	NPC272194
0.9012	High Similarity	NPC92589
0.9012	High Similarity	NPC14822
0.9	High Similarity	NPC19860
0.8994	High Similarity	NPC213608
0.8994	High Similarity	NPC1477
0.8987	High Similarity	NPC98028
0.8987	High Similarity	NPC170169
0.8987	High Similarity	NPC290671
0.8974	High Similarity	NPC130581
0.8974	High Similarity	NPC12148
0.8957	High Similarity	NPC193998
0.8951	High Similarity	NPC49009
0.8951	High Similarity	NPC169
0.8951	High Similarity	NPC303210
0.8951	High Similarity	NPC95472
0.8951	High Similarity	NPC239270
0.8944	High Similarity	NPC269495
0.8944	High Similarity	NPC260902
0.8944	High Similarity	NPC210048
0.8944	High Similarity	NPC296957
0.8944	High Similarity	NPC268360
0.8931	High Similarity	NPC476238
0.8931	High Similarity	NPC31627
0.8931	High Similarity	NPC41326
0.8931	High Similarity	NPC5871
0.8931	High Similarity	NPC327269
0.8924	High Similarity	NPC78335
0.8924	High Similarity	NPC230713
0.8917	High Similarity	NPC135325
0.8917	High Similarity	NPC211811
0.891	High Similarity	NPC51641
0.891	High Similarity	NPC210826
0.891	High Similarity	NPC124729
0.891	High Similarity	NPC306488
0.891	High Similarity	NPC178343
0.891	High Similarity	NPC470322
0.891	High Similarity	NPC154217
0.891	High Similarity	NPC5820
0.891	High Similarity	NPC300267
0.8902	High Similarity	NPC109180
0.8896	High Similarity	NPC45124
0.8896	High Similarity	NPC30655
0.8896	High Similarity	NPC74854
0.8889	High Similarity	NPC311574
0.8889	High Similarity	NPC264932
0.8889	High Similarity	NPC40583
0.8882	High Similarity	NPC247677
0.8882	High Similarity	NPC160015
0.8876	High Similarity	NPC164384
0.8875	High Similarity	NPC236756
0.8875	High Similarity	NPC72370
0.8875	High Similarity	NPC311579
0.8869	High Similarity	NPC261471
0.8868	High Similarity	NPC295650
0.8868	High Similarity	NPC471675
0.8861	High Similarity	NPC317492
0.8861	High Similarity	NPC470461
0.8861	High Similarity	NPC39929
0.8861	High Similarity	NPC178202
0.8861	High Similarity	NPC296030
0.8855	High Similarity	NPC320789
0.8846	High Similarity	NPC273538
0.8846	High Similarity	NPC234629
0.8846	High Similarity	NPC1886
0.8846	High Similarity	NPC196137
0.8846	High Similarity	NPC326500
0.8846	High Similarity	NPC311741
0.8846	High Similarity	NPC216538
0.8846	High Similarity	NPC469953
0.8841	High Similarity	NPC272722
0.8834	High Similarity	NPC304839
0.8834	High Similarity	NPC220582
0.8834	High Similarity	NPC172687
0.8827	High Similarity	NPC476930
0.8827	High Similarity	NPC270044
0.8827	High Similarity	NPC161650
0.882	High Similarity	NPC476169
0.882	High Similarity	NPC148938
0.882	High Similarity	NPC99199
0.882	High Similarity	NPC198490
0.8812	High Similarity	NPC473996
0.8812	High Similarity	NPC285623
0.8812	High Similarity	NPC210597
0.8805	High Similarity	NPC61258
0.8805	High Similarity	NPC155882
0.8805	High Similarity	NPC472421
0.8805	High Similarity	NPC191104
0.8805	High Similarity	NPC474735
0.8805	High Similarity	NPC180351
0.8797	High Similarity	NPC296869
0.8797	High Similarity	NPC168085
0.8797	High Similarity	NPC470460
0.8797	High Similarity	NPC161864
0.8797	High Similarity	NPC208303
0.8797	High Similarity	NPC244407
0.879	High Similarity	NPC153758
0.879	High Similarity	NPC181388
0.8782	High Similarity	NPC158874
0.8782	High Similarity	NPC94794
0.8782	High Similarity	NPC112791
0.8782	High Similarity	NPC212932
0.8782	High Similarity	NPC190637
0.8782	High Similarity	NPC9117
0.8782	High Similarity	NPC24821
0.8782	High Similarity	NPC188632
0.8782	High Similarity	NPC87609
0.8782	High Similarity	NPC293053
0.8782	High Similarity	NPC17262
0.8782	High Similarity	NPC225884
0.8782	High Similarity	NPC470296
0.8782	High Similarity	NPC302181
0.8782	High Similarity	NPC470216
0.8782	High Similarity	NPC196459
0.8773	High Similarity	NPC476350
0.8773	High Similarity	NPC476349
0.8765	High Similarity	NPC13879
0.8765	High Similarity	NPC107244
0.8758	High Similarity	NPC209760
0.8758	High Similarity	NPC235333
0.8758	High Similarity	NPC183874
0.8758	High Similarity	NPC122365
0.8758	High Similarity	NPC100134
0.8758	High Similarity	NPC41719
0.8757	High Similarity	NPC37606
0.8757	High Similarity	NPC65885
0.8757	High Similarity	NPC233956
0.875	High Similarity	NPC471229
0.875	High Similarity	NPC472423
0.875	High Similarity	NPC472580
0.875	High Similarity	NPC474772
0.875	High Similarity	NPC472636
0.875	High Similarity	NPC78830
0.875	High Similarity	NPC474744
0.875	High Similarity	NPC51404
0.875	High Similarity	NPC218533
0.8742	High Similarity	NPC88445
0.8742	High Similarity	NPC469932
0.8742	High Similarity	NPC477941
0.8735	High Similarity	NPC136641
0.8735	High Similarity	NPC36320
0.8734	High Similarity	NPC180477
0.8734	High Similarity	NPC129650
0.8734	High Similarity	NPC249942
0.8734	High Similarity	NPC297886
0.8734	High Similarity	NPC17816
0.8734	High Similarity	NPC14001
0.8734	High Similarity	NPC140120
0.8734	High Similarity	NPC166757
0.8726	High Similarity	NPC230943
0.8726	High Similarity	NPC178627
0.8726	High Similarity	NPC469935
0.8721	High Similarity	NPC97523
0.872	High Similarity	NPC306978
0.8718	High Similarity	NPC473042
0.8718	High Similarity	NPC226636
0.8718	High Similarity	NPC53192
0.8718	High Similarity	NPC36181
0.8718	High Similarity	NPC200694
0.8718	High Similarity	NPC11561
0.8718	High Similarity	NPC313036
0.8712	High Similarity	NPC212967
0.8712	High Similarity	NPC96342
0.8712	High Similarity	NPC164110
0.8712	High Similarity	NPC246647
0.8706	High Similarity	NPC53917
0.8706	High Similarity	NPC224165
0.8704	High Similarity	NPC297531
0.8704	High Similarity	NPC474542
0.8704	High Similarity	NPC213936
0.8704	High Similarity	NPC250769

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 NPC323137 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	943
0.2-0.3	1696
0.3-0.4	2603
0.4-0.5	2028
0.5-0.6	1030
0.6-0.7	333
0.7-0.8	125
0.8-0.85	42
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8846	High Similarity	NPD4378	Clinical (unspecified phase)
0.8827	High Similarity	NPD7075	Discontinued
0.8758	High Similarity	NPD7096	Clinical (unspecified phase)
0.8712	High Similarity	NPD3749	Approved
0.8696	High Similarity	NPD6801	Discontinued
0.8616	High Similarity	NPD920	Approved
0.8545	High Similarity	NPD919	Approved
0.8544	High Similarity	NPD6799	Approved
0.8526	High Similarity	NPD1243	Approved
0.8491	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD3882	Suspended
0.8405	Intermediate Similarity	NPD7411	Suspended
0.8365	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD3817	Phase 2
0.8344	Intermediate Similarity	NPD6599	Discontinued
0.8344	Intermediate Similarity	NPD4380	Phase 2
0.8324	Intermediate Similarity	NPD6559	Discontinued
0.8256	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD7473	Discontinued
0.8225	Intermediate Similarity	NPD1247	Approved
0.8204	Intermediate Similarity	NPD7768	Phase 2
0.8193	Intermediate Similarity	NPD2801	Approved
0.8193	Intermediate Similarity	NPD7819	Suspended
0.8193	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6232	Discontinued
0.8165	Intermediate Similarity	NPD2344	Approved
0.816	Intermediate Similarity	NPD5403	Approved
0.8155	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD1510	Phase 2
0.8144	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD5402	Approved
0.8129	Intermediate Similarity	NPD3926	Phase 2
0.8113	Intermediate Similarity	NPD1549	Phase 2
0.8101	Intermediate Similarity	NPD2796	Approved
0.8098	Intermediate Similarity	NPD1512	Approved
0.8092	Intermediate Similarity	NPD3818	Discontinued
0.8063	Intermediate Similarity	NPD2800	Approved
0.8063	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD5494	Approved
0.805	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD5401	Approved
0.8024	Intermediate Similarity	NPD1934	Approved
0.8013	Intermediate Similarity	NPD1240	Approved
0.8012	Intermediate Similarity	NPD3750	Approved
0.7988	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD6166	Phase 2
0.7977	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1511	Approved
0.7966	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD2309	Approved
0.7943	Intermediate Similarity	NPD5844	Phase 1
0.7927	Intermediate Similarity	NPD2533	Approved
0.7927	Intermediate Similarity	NPD2532	Approved
0.7927	Intermediate Similarity	NPD2534	Approved
0.7925	Intermediate Similarity	NPD2799	Discontinued
0.7911	Intermediate Similarity	NPD1607	Approved
0.7888	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD2313	Discontinued
0.7875	Intermediate Similarity	NPD2935	Discontinued
0.7853	Intermediate Similarity	NPD6797	Phase 2
0.7826	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD7251	Discontinued
0.7803	Intermediate Similarity	NPD6959	Discontinued
0.779	Intermediate Similarity	NPD8434	Phase 2
0.7765	Intermediate Similarity	NPD7808	Phase 3
0.7764	Intermediate Similarity	NPD1551	Phase 2
0.7753	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD5953	Discontinued
0.7742	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7286	Phase 2
0.7738	Intermediate Similarity	NPD3226	Approved
0.7705	Intermediate Similarity	NPD4287	Approved
0.7702	Intermediate Similarity	NPD3748	Approved
0.7683	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD1465	Phase 2
0.7658	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7054	Approved
0.7622	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7074	Phase 3
0.7598	Intermediate Similarity	NPD7472	Approved
0.7584	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6651	Approved
0.7576	Intermediate Similarity	NPD4628	Phase 3
0.7564	Intermediate Similarity	NPD1203	Approved
0.7557	Intermediate Similarity	NPD7229	Phase 3
0.7547	Intermediate Similarity	NPD3268	Approved
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1471	Phase 3
0.75	Intermediate Similarity	NPD2346	Discontinued
0.7485	Intermediate Similarity	NPD7033	Discontinued
0.7485	Intermediate Similarity	NPD4308	Phase 3
0.7472	Intermediate Similarity	NPD2403	Approved
0.747	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2797	Approved
0.7438	Intermediate Similarity	NPD3764	Approved
0.7438	Intermediate Similarity	NPD6798	Discontinued
0.7421	Intermediate Similarity	NPD6832	Phase 2
0.7414	Intermediate Similarity	NPD2296	Approved
0.7407	Intermediate Similarity	NPD5124	Phase 1
0.7407	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6355	Discontinued
0.7407	Intermediate Similarity	NPD447	Suspended
0.7389	Intermediate Similarity	NPD3751	Discontinued
0.7386	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD9717	Approved
0.736	Intermediate Similarity	NPD5710	Approved
0.736	Intermediate Similarity	NPD5711	Approved
0.736	Intermediate Similarity	NPD6808	Phase 2
0.7353	Intermediate Similarity	NPD5049	Phase 3
0.7351	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD8313	Approved
0.7337	Intermediate Similarity	NPD8312	Approved
0.7337	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7458	Discontinued
0.7321	Intermediate Similarity	NPD2354	Approved
0.7308	Intermediate Similarity	NPD422	Phase 1
0.7303	Intermediate Similarity	NPD7199	Phase 2
0.7296	Intermediate Similarity	NPD2798	Approved
0.7294	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6233	Phase 2
0.7278	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD3787	Discontinued
0.7262	Intermediate Similarity	NPD7003	Approved
0.7239	Intermediate Similarity	NPD4060	Phase 1
0.7239	Intermediate Similarity	NPD943	Approved
0.7239	Intermediate Similarity	NPD4307	Phase 2
0.7235	Intermediate Similarity	NPD7390	Discontinued
0.7233	Intermediate Similarity	NPD3267	Approved
0.7233	Intermediate Similarity	NPD3266	Approved
0.7231	Intermediate Similarity	NPD7435	Discontinued
0.7229	Intermediate Similarity	NPD6100	Approved
0.7229	Intermediate Similarity	NPD6099	Approved
0.7225	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4361	Phase 2
0.7225	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8150	Discontinued
0.7219	Intermediate Similarity	NPD3887	Approved
0.7219	Intermediate Similarity	NPD6190	Approved
0.7205	Intermediate Similarity	NPD4908	Phase 1
0.72	Intermediate Similarity	NPD6280	Approved
0.72	Intermediate Similarity	NPD37	Approved
0.72	Intermediate Similarity	NPD6279	Approved
0.7195	Intermediate Similarity	NPD1933	Approved
0.7195	Intermediate Similarity	NPD230	Phase 1
0.7195	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6234	Discontinued
0.7186	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD2353	Approved
0.7175	Intermediate Similarity	NPD4967	Phase 2
0.7175	Intermediate Similarity	NPD4966	Approved
0.7175	Intermediate Similarity	NPD4965	Approved
0.7173	Intermediate Similarity	NPD4363	Phase 3
0.7173	Intermediate Similarity	NPD4360	Phase 2
0.717	Intermediate Similarity	NPD3225	Approved
0.7159	Intermediate Similarity	NPD5760	Phase 2
0.7159	Intermediate Similarity	NPD5761	Phase 2
0.7135	Intermediate Similarity	NPD6764	Approved
0.7135	Intermediate Similarity	NPD6765	Approved
0.7126	Intermediate Similarity	NPD5405	Approved
0.7126	Intermediate Similarity	NPD5406	Approved
0.7126	Intermediate Similarity	NPD5404	Approved
0.7126	Intermediate Similarity	NPD5408	Approved
0.7121	Intermediate Similarity	NPD7584	Approved
0.712	Intermediate Similarity	NPD1729	Discontinued
0.7119	Intermediate Similarity	NPD4288	Approved
0.7088	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6782	Approved
0.7077	Intermediate Similarity	NPD6777	Approved
0.7077	Intermediate Similarity	NPD6779	Approved
0.7077	Intermediate Similarity	NPD6778	Approved
0.7077	Intermediate Similarity	NPD6781	Approved
0.7077	Intermediate Similarity	NPD6776	Approved
0.7077	Intermediate Similarity	NPD6780	Approved
0.7065	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7783	Phase 2
0.7062	Intermediate Similarity	NPD8455	Phase 2
0.705	Intermediate Similarity	NPD8151	Discontinued
0.7044	Intermediate Similarity	NPD1608	Approved
0.702	Intermediate Similarity	NPD7870	Phase 2
0.702	Intermediate Similarity	NPD7871	Phase 2
0.7019	Intermediate Similarity	NPD1164	Approved
0.7015	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7874	Approved
0.7012	Intermediate Similarity	NPD411	Approved
0.7012	Intermediate Similarity	NPD1296	Phase 2
0.7	Intermediate Similarity	NPD2654	Approved
0.7	Intermediate Similarity	NPD1652	Phase 2
0.7	Intermediate Similarity	NPD7585	Approved
0.699	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6585	Discontinued

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