NPASS Compound

Structure

CID325740 OpenBabel06191716182D 39 42 0 0 1 0 0 0 0 0999 V2000 -0.0011 5.5730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6100 5.5727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4453 0.6949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2813 -0.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2184 2.7856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4141 3.2502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4651 -1.7331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9292 -0.9285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1405 2.9443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 3.1633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4020 2.0532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5971 2.4912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7611 1.3812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8053 4.1795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6096 3.7149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9020 1.1479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0005 0.9289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6085 -0.9295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8050 2.3216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8054 5.1084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5429 0.4759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8587 1.6002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6094 2.7861 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.6088 -0.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8039 -1.3936 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.2178 0.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4135 0.4638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8046 0.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 1.8572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4139 2.3213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0004 -0.9289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8048 1.3930 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.4137 1.3927 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.7409 -0.8539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2178 -0.0007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6093 2.7860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6077 -2.7872 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 -0.8035 -2.3225 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 7 31 1 0 0 0 0 8 31 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 22 2 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 20 2 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 17 32 1 0 0 0 0 18 24 1 0 0 0 0 18 25 1 0 0 0 0 19 23 1 0 0 0 0 19 32 1 0 0 0 0 22 26 1 0 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 28 2 0 0 0 0 25 31 1 0 0 0 0 25 39 1 0 0 0 0 26 33 1 0 0 0 0 26 34 2 0 0 0 0 27 33 1 0 0 0 0 27 35 2 0 0 0 0 28 32 1 0 0 0 0 28 38 1 0 0 0 0 29 32 1 0 0 0 0 29 33 1 0 0 0 0 29 36 2 0 0 0 0 30 33 1 0 0 0 0 31 38 1 0 0 0 0 37 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.3
Volume:	574.111
LogP:	6.924
LogD:	5.828
LogS:	-4.699
# Rotatable Bonds:	7
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.132
Synthetic Accessibility Score:	5.636
Fsp3:	0.545
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.03
MDCK Permeability:	1.928188794408925e-05
Pgp-inhibitor:	0.399
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.062
20% Bioavailability (F20%):	0.208
30% Bioavailability (F30%):	0.637

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	96.05994415283203%
Volume Distribution (VD):	2.197
Pgp-substrate:	4.627281188964844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.303
CYP2C19-inhibitor:	0.442
CYP2C19-substrate:	0.928
CYP2C9-inhibitor:	0.618
CYP2C9-substrate:	0.734
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.709
CYP3A4-substrate:	0.917

ADMET: Excretion

Clearance (CL):	12.391
Half-life (T1/2):	0.015

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.687
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.637
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.023
Carcinogencity:	0.687
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC325740

Natural Product ID:	NPC325740
*Common Name:**	Ochrocarpinone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LCJOSIBQVUSWIH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C33H42O6/c1-20(2)14-15-23-19-32(17-16-21(3)4)28-24(18-25(39-37)31(7,8)38-28)27(35)33(29(32)36,30(23,5)6)26(34)22-12-10-9-11-13-22/h9-14,16,23,25,37H,15,17-19H2,1-8H3
SMILES:	CC(=CCC1CC2(C3=C(CC(C(O3)(C)C)OO)C(=O)C(C2=O)(C1(C)C)C(=O)C4=CC=CC=C4)CC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486622
PubChem CID:	10347061
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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	=	6.9	ug.mL-1	PMID[468091]

☑ 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 NPC325740 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	275
0.1-0.2	1194
0.2-0.3	2186
0.3-0.4	6334
0.4-0.5	13228
0.5-0.6	13767
0.6-0.7	5348
0.7-0.8	317
0.8-0.85	14
0.85-0.9	20
0.9-0.95	13
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9339	High Similarity	NPC328997
0.9339	High Similarity	NPC294050
0.9187	High Similarity	NPC316553
0.9106	High Similarity	NPC146239
0.9068	High Similarity	NPC61651
0.906	High Similarity	NPC260886
0.8908	High Similarity	NPC268930
0.8828	High Similarity	NPC144257
0.8689	High Similarity	NPC476225
0.8559	High Similarity	NPC218855
0.8417	Intermediate Similarity	NPC234637
0.8417	Intermediate Similarity	NPC130591
0.8385	Intermediate Similarity	NPC471334
0.8376	Intermediate Similarity	NPC470007
0.8346	Intermediate Similarity	NPC472694
0.8346	Intermediate Similarity	NPC472693
0.8346	Intermediate Similarity	NPC478108
0.8333	Intermediate Similarity	NPC471481
0.832	Intermediate Similarity	NPC476234
0.8125	Intermediate Similarity	NPC328107
0.8125	Intermediate Similarity	NPC472681
0.803	Intermediate Similarity	NPC471832
0.7958	Intermediate Similarity	NPC273798
0.7956	Intermediate Similarity	NPC118366
0.7953	Intermediate Similarity	NPC472680
0.7953	Intermediate Similarity	NPC472679
0.7953	Intermediate Similarity	NPC105709
0.7907	Intermediate Similarity	NPC65627
0.7886	Intermediate Similarity	NPC477475
0.7886	Intermediate Similarity	NPC477476
0.7874	Intermediate Similarity	NPC202015
0.7869	Intermediate Similarity	NPC137315
0.7857	Intermediate Similarity	NPC323440
0.7857	Intermediate Similarity	NPC222968
0.7857	Intermediate Similarity	NPC80605
0.7847	Intermediate Similarity	NPC132810
0.7846	Intermediate Similarity	NPC318067
0.7836	Intermediate Similarity	NPC472692
0.7836	Intermediate Similarity	NPC472682
0.7823	Intermediate Similarity	NPC326664
0.7823	Intermediate Similarity	NPC241851
0.7823	Intermediate Similarity	NPC294458
0.7812	Intermediate Similarity	NPC475827
0.7812	Intermediate Similarity	NPC474223
0.7803	Intermediate Similarity	NPC81135
0.7795	Intermediate Similarity	NPC472697
0.7795	Intermediate Similarity	NPC472698
0.7778	Intermediate Similarity	NPC209851
0.7769	Intermediate Similarity	NPC474159
0.7769	Intermediate Similarity	NPC474254
0.7761	Intermediate Similarity	NPC262819
0.776	Intermediate Similarity	NPC215419
0.7744	Intermediate Similarity	NPC115797
0.7744	Intermediate Similarity	NPC51448
0.7742	Intermediate Similarity	NPC470253
0.7724	Intermediate Similarity	NPC46549
0.7724	Intermediate Similarity	NPC264229
0.7724	Intermediate Similarity	NPC265513
0.7724	Intermediate Similarity	NPC306799
0.7724	Intermediate Similarity	NPC101043
0.7708	Intermediate Similarity	NPC471970
0.7705	Intermediate Similarity	NPC192577
0.7692	Intermediate Similarity	NPC144247
0.7692	Intermediate Similarity	NPC469375
0.7692	Intermediate Similarity	NPC294679
0.7692	Intermediate Similarity	NPC8493
0.7692	Intermediate Similarity	NPC145301
0.768	Intermediate Similarity	NPC196075
0.7674	Intermediate Similarity	NPC238861
0.7674	Intermediate Similarity	NPC77000
0.7669	Intermediate Similarity	NPC473423
0.7669	Intermediate Similarity	NPC48992
0.7669	Intermediate Similarity	NPC470648
0.7656	Intermediate Similarity	NPC318173
0.7647	Intermediate Similarity	NPC472394
0.763	Intermediate Similarity	NPC25736
0.7627	Intermediate Similarity	NPC476042
0.7619	Intermediate Similarity	NPC217111
0.7615	Intermediate Similarity	NPC472981
0.7612	Intermediate Similarity	NPC472678
0.7612	Intermediate Similarity	NPC478165
0.7612	Intermediate Similarity	NPC478162
0.7609	Intermediate Similarity	NPC23894
0.76	Intermediate Similarity	NPC143768
0.7594	Intermediate Similarity	NPC236405
0.7583	Intermediate Similarity	NPC475939
0.7583	Intermediate Similarity	NPC474866
0.7583	Intermediate Similarity	NPC471829
0.7583	Intermediate Similarity	NPC472691
0.7578	Intermediate Similarity	NPC94425
0.7578	Intermediate Similarity	NPC152812
0.7576	Intermediate Similarity	NPC51079
0.7576	Intermediate Similarity	NPC469742
0.7569	Intermediate Similarity	NPC469854
0.7569	Intermediate Similarity	NPC469856
0.7559	Intermediate Similarity	NPC226093
0.7559	Intermediate Similarity	NPC62138
0.7559	Intermediate Similarity	NPC471616
0.7556	Intermediate Similarity	NPC225103
0.7552	Intermediate Similarity	NPC30846
0.7552	Intermediate Similarity	NPC471972
0.7552	Intermediate Similarity	NPC469855
0.7552	Intermediate Similarity	NPC471971
0.7538	Intermediate Similarity	NPC474222
0.7538	Intermediate Similarity	NPC475804
0.7537	Intermediate Similarity	NPC470753
0.7537	Intermediate Similarity	NPC473220
0.7536	Intermediate Similarity	NPC203486
0.7536	Intermediate Similarity	NPC329913
0.7534	Intermediate Similarity	NPC112216
0.7534	Intermediate Similarity	NPC7095
0.752	Intermediate Similarity	NPC292834
0.752	Intermediate Similarity	NPC212415
0.752	Intermediate Similarity	NPC280789
0.7518	Intermediate Similarity	NPC183270
0.7518	Intermediate Similarity	NPC477904
0.75	Intermediate Similarity	NPC7464
0.75	Intermediate Similarity	NPC472388
0.75	Intermediate Similarity	NPC127857
0.75	Intermediate Similarity	NPC473443
0.75	Intermediate Similarity	NPC184109
0.7483	Intermediate Similarity	NPC477468
0.7481	Intermediate Similarity	NPC144547
0.7481	Intermediate Similarity	NPC195224
0.748	Intermediate Similarity	NPC228936
0.748	Intermediate Similarity	NPC470764
0.7467	Intermediate Similarity	NPC305710
0.7466	Intermediate Similarity	NPC81698
0.7466	Intermediate Similarity	NPC60509
0.7466	Intermediate Similarity	NPC250046
0.7465	Intermediate Similarity	NPC294330
0.7464	Intermediate Similarity	NPC472656
0.7463	Intermediate Similarity	NPC470765
0.7462	Intermediate Similarity	NPC476645
0.7462	Intermediate Similarity	NPC204784
0.7447	Intermediate Similarity	NPC472371
0.7447	Intermediate Similarity	NPC472395
0.7445	Intermediate Similarity	NPC472361
0.7445	Intermediate Similarity	NPC472418
0.7444	Intermediate Similarity	NPC140118
0.7444	Intermediate Similarity	NPC85511
0.7444	Intermediate Similarity	NPC12881
0.7442	Intermediate Similarity	NPC471553
0.7438	Intermediate Similarity	NPC247976
0.7432	Intermediate Similarity	NPC472548
0.7422	Intermediate Similarity	NPC135730
0.7419	Intermediate Similarity	NPC475282
0.7415	Intermediate Similarity	NPC254558
0.7415	Intermediate Similarity	NPC165260
0.7415	Intermediate Similarity	NPC161239
0.7415	Intermediate Similarity	NPC198455
0.7415	Intermediate Similarity	NPC91730
0.7413	Intermediate Similarity	NPC63737
0.741	Intermediate Similarity	NPC310662
0.741	Intermediate Similarity	NPC126516
0.7407	Intermediate Similarity	NPC190849
0.7407	Intermediate Similarity	NPC171007
0.7407	Intermediate Similarity	NPC474106
0.7405	Intermediate Similarity	NPC988
0.7405	Intermediate Similarity	NPC232958
0.7405	Intermediate Similarity	NPC289432
0.7402	Intermediate Similarity	NPC477411
0.7402	Intermediate Similarity	NPC67377
0.7398	Intermediate Similarity	NPC25385
0.7398	Intermediate Similarity	NPC193640
0.7398	Intermediate Similarity	NPC100767
0.7398	Intermediate Similarity	NPC475905
0.7395	Intermediate Similarity	NPC145052
0.7394	Intermediate Similarity	NPC473779
0.7394	Intermediate Similarity	NPC473479
0.7394	Intermediate Similarity	NPC46242
0.7394	Intermediate Similarity	NPC165191
0.7394	Intermediate Similarity	NPC149773
0.7394	Intermediate Similarity	NPC28592
0.7394	Intermediate Similarity	NPC91887
0.7394	Intermediate Similarity	NPC5014
0.7394	Intermediate Similarity	NPC114333
0.7394	Intermediate Similarity	NPC469857
0.7394	Intermediate Similarity	NPC157284
0.7394	Intermediate Similarity	NPC477849
0.7394	Intermediate Similarity	NPC475400
0.7394	Intermediate Similarity	NPC245760
0.7394	Intermediate Similarity	NPC23667
0.7394	Intermediate Similarity	NPC289358
0.7394	Intermediate Similarity	NPC42384
0.7394	Intermediate Similarity	NPC50615
0.7394	Intermediate Similarity	NPC51531
0.7394	Intermediate Similarity	NPC297797
0.7391	Intermediate Similarity	NPC475493
0.7388	Intermediate Similarity	NPC295664
0.7383	Intermediate Similarity	NPC237549
0.7383	Intermediate Similarity	NPC473414
0.7383	Intermediate Similarity	NPC1173
0.7383	Intermediate Similarity	NPC77719
0.7383	Intermediate Similarity	NPC265395
0.7383	Intermediate Similarity	NPC472005
0.7383	Intermediate Similarity	NPC256142
0.7383	Intermediate Similarity	NPC304876
0.7383	Intermediate Similarity	NPC472030
0.7383	Intermediate Similarity	NPC472022

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 NPC325740 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	843
0.2-0.3	1327
0.3-0.4	3076
0.4-0.5	2360
0.5-0.6	1123
0.6-0.7	158
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7752	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7094	Approved
0.76	Intermediate Similarity	NPD6858	Approved
0.752	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7961	Discontinued
0.7311	Intermediate Similarity	NPD3495	Discontinued
0.7308	Intermediate Similarity	NPD7610	Discontinued
0.7252	Intermediate Similarity	NPD7009	Phase 2
0.7154	Intermediate Similarity	NPD3317	Approved
0.7143	Intermediate Similarity	NPD7236	Approved
0.7119	Intermediate Similarity	NPD7631	Approved
0.7101	Intermediate Similarity	NPD7084	Phase 3
0.7034	Intermediate Similarity	NPD7609	Phase 3
0.7016	Intermediate Similarity	NPD1929	Approved
0.7016	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD1930	Approved
0.7	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD7798	Approved
0.6911	Remote Similarity	NPD2066	Phase 3
0.6908	Remote Similarity	NPD7239	Suspended
0.6875	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD3972	Approved
0.6838	Remote Similarity	NPD4879	Approved
0.6825	Remote Similarity	NPD5909	Discontinued
0.6818	Remote Similarity	NPD5951	Approved
0.6818	Remote Similarity	NPD2629	Approved
0.68	Remote Similarity	NPD1932	Approved
0.6779	Remote Similarity	NPD8166	Discontinued
0.6777	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7008	Discontinued
0.6753	Remote Similarity	NPD7458	Discontinued
0.6748	Remote Similarity	NPD7799	Discontinued
0.6744	Remote Similarity	NPD2329	Discontinued
0.6742	Remote Similarity	NPD6010	Discontinued
0.6739	Remote Similarity	NPD4878	Approved
0.6736	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD650	Approved
0.6692	Remote Similarity	NPD2067	Discontinued
0.669	Remote Similarity	NPD7055	Discontinued
0.6667	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD1989	Approved
0.6667	Remote Similarity	NPD7713	Phase 3
0.6667	Remote Similarity	NPD2798	Approved
0.6615	Remote Similarity	NPD2182	Approved
0.6614	Remote Similarity	NPD6647	Phase 2
0.6588	Remote Similarity	NPD8434	Phase 2
0.6587	Remote Similarity	NPD8368	Discontinued
0.6577	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD1237	Approved
0.6549	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD6287	Discontinued
0.651	Remote Similarity	NPD2796	Approved
0.65	Remote Similarity	NPD7058	Phase 2
0.65	Remote Similarity	NPD7057	Phase 3
0.6497	Remote Similarity	NPD4380	Phase 2
0.6483	Remote Similarity	NPD2313	Discontinued
0.6479	Remote Similarity	NPD1470	Approved
0.6471	Remote Similarity	NPD8407	Phase 2
0.6467	Remote Similarity	NPD2346	Discontinued
0.6467	Remote Similarity	NPD1471	Phase 3
0.6452	Remote Similarity	NPD6273	Approved
0.6444	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD7305	Phase 1
0.6443	Remote Similarity	NPD2799	Discontinued
0.6439	Remote Similarity	NPD1317	Discontinued
0.6438	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD1088	Approved
0.6423	Remote Similarity	NPD1508	Approved
0.6416	Remote Similarity	NPD8360	Approved
0.6416	Remote Similarity	NPD8361	Approved
0.6416	Remote Similarity	NPD8435	Approved
0.6408	Remote Similarity	NPD1876	Approved
0.6403	Remote Similarity	NPD2932	Approved
0.6397	Remote Similarity	NPD4198	Discontinued
0.6395	Remote Similarity	NPD8150	Discontinued
0.6393	Remote Similarity	NPD3672	Approved
0.6393	Remote Similarity	NPD3673	Approved
0.6392	Remote Similarity	NPD6599	Discontinued
0.6385	Remote Similarity	NPD5048	Discontinued
0.6383	Remote Similarity	NPD6637	Approved
0.638	Remote Similarity	NPD5494	Approved
0.6375	Remote Similarity	NPD7819	Suspended
0.6375	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3300	Phase 2
0.6357	Remote Similarity	NPD3026	Approved
0.6357	Remote Similarity	NPD3023	Approved
0.634	Remote Similarity	NPD7003	Approved
0.6331	Remote Similarity	NPD3025	Approved
0.6331	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD3024	Approved
0.6327	Remote Similarity	NPD7715	Approved
0.6327	Remote Similarity	NPD7714	Approved
0.6327	Remote Similarity	NPD6663	Approved
0.6325	Remote Similarity	NPD942	Approved
0.632	Remote Similarity	NPD1693	Approved
0.6312	Remote Similarity	NPD1201	Approved
0.6308	Remote Similarity	NPD164	Approved
0.6304	Remote Similarity	NPD6065	Approved
0.6301	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD3019	Approved
0.6282	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD1087	Approved
0.6276	Remote Similarity	NPD5736	Approved
0.6273	Remote Similarity	NPD5760	Phase 2
0.6273	Remote Similarity	NPD5761	Phase 2
0.627	Remote Similarity	NPD1843	Approved
0.626	Remote Similarity	NPD1090	Approved
0.626	Remote Similarity	NPD1089	Approved
0.626	Remote Similarity	NPD1086	Approved
0.6259	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD7741	Discontinued
0.6258	Remote Similarity	NPD7075	Discontinued
0.625	Remote Similarity	NPD2652	Approved
0.625	Remote Similarity	NPD2344	Approved
0.625	Remote Similarity	NPD2650	Approved
0.625	Remote Similarity	NPD1238	Approved
0.624	Remote Similarity	NPD1202	Approved
0.6233	Remote Similarity	NPD6832	Phase 2
0.6232	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD1510	Phase 2
0.6225	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD8165	Discontinued
0.6218	Remote Similarity	NPD3950	Discontinued
0.6216	Remote Similarity	NPD8032	Phase 2
0.6213	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD6685	Approved
0.6211	Remote Similarity	NPD6801	Discontinued
0.6204	Remote Similarity	NPD4766	Approved
0.6201	Remote Similarity	NPD8485	Approved
0.6197	Remote Similarity	NPD4807	Approved
0.6197	Remote Similarity	NPD4806	Approved
0.6194	Remote Similarity	NPD4233	Approved
0.6194	Remote Similarity	NPD3887	Approved
0.6194	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD4234	Approved
0.619	Remote Similarity	NPD6039	Approved
0.619	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD7028	Phase 2
0.6181	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD800	Approved
0.6178	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.617	Remote Similarity	NPD5306	Approved
0.617	Remote Similarity	NPD2345	Approved
0.617	Remote Similarity	NPD5305	Approved
0.6169	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD7115	Discovery
0.6158	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD3764	Approved
0.6145	Remote Similarity	NPD8127	Discontinued
0.6144	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD1241	Discontinued
0.6129	Remote Similarity	NPD7487	Discontinued
0.6127	Remote Similarity	NPD8313	Approved
0.6127	Remote Similarity	NPD8312	Approved
0.6125	Remote Similarity	NPD3226	Approved
0.6125	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD3748	Approved
0.6118	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD4576	Approved
0.6115	Remote Similarity	NPD6799	Approved
0.6115	Remote Similarity	NPD4574	Approved
0.6111	Remote Similarity	NPD6844	Discontinued
0.6111	Remote Similarity	NPD5157	Phase 1
0.6111	Remote Similarity	NPD1563	Approved
0.6111	Remote Similarity	NPD5159	Phase 2
0.6111	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6764	Approved
0.6105	Remote Similarity	NPD6765	Approved
0.6104	Remote Similarity	NPD1549	Phase 2
0.6101	Remote Similarity	NPD5403	Approved
0.6099	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD6085	Phase 2
0.6095	Remote Similarity	NPD7473	Discontinued
0.6094	Remote Similarity	NPD1564	Approved
0.6094	Remote Similarity	NPD1565	Approved
0.6094	Remote Similarity	NPD1566	Phase 3
0.6093	Remote Similarity	NPD6651	Approved
0.609	Remote Similarity	NPD2309	Approved
0.609	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD1711	Phase 2
0.608	Remote Similarity	NPD1239	Approved
0.6078	Remote Similarity	NPD5405	Approved
0.6078	Remote Similarity	NPD2438	Suspended
0.6078	Remote Similarity	NPD6100	Approved
0.6078	Remote Similarity	NPD5406	Approved
0.6078	Remote Similarity	NPD5404	Approved
0.6078	Remote Similarity	NPD6099	Approved
0.6078	Remote Similarity	NPD5408	Approved
0.6077	Remote Similarity	NPD3135	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