NPASS Compound

Structure

NPC33913 OpenBabel07101718322D 29 32 0 0 1 0 0 0 0 0999 V2000 1.5417 4.0385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1816 5.7327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8363 2.9680 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 2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4980 4.4543 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 0.8660 1.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8508 4.9895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 2.7601 0.0000 C 0 0 2 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 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8289 5.1974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1379 6.1485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 6 11 2 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 19 2 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 25 1 0 0 0 0 18 3 1 1 0 0 0 18 22 1 0 0 0 0 19 26 1 0 0 0 0 20 28 1 1 0 0 0 21 8 1 6 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 27 1 1 0 0 0 23 27 1 1 0 0 0 24 26 1 1 0 0 0 25 29 2 0 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.32
Volume:	450.993
LogP:	5.93
LogD:	4.511
LogS:	-4.734
# Rotatable Bonds:	4
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.55
Synthetic Accessibility Score:	4.495
Fsp3:	0.815
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:	-4.562
MDCK Permeability:	1.1447083124949131e-05
Pgp-inhibitor:	0.959
Pgp-substrate:	0.878
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.927

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.743
Plasma Protein Binding (PPB):	95.25609588623047%
Volume Distribution (VD):	1.049
Pgp-substrate:	2.095768928527832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.161
CYP1A2-substrate:	0.256
CYP2C19-inhibitor:	0.15
CYP2C19-substrate:	0.843
CYP2C9-inhibitor:	0.335
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.059
CYP2D6-substrate:	0.595
CYP3A4-inhibitor:	0.813
CYP3A4-substrate:	0.456

ADMET: Excretion

Clearance (CL):	17.465
Half-life (T1/2):	0.084

ADMET: Toxicity

hERG Blockers:	0.432
Human Hepatotoxicity (H-HT):	0.409
Drug-inuced Liver Injury (DILI):	0.437
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.732
Maximum Recommended Daily Dose:	0.878
Skin Sensitization:	0.92
Carcinogencity:	0.907
Eye Corrosion:	0.041
Eye Irritation:	0.05
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC33913

Natural Product ID:	NPC33913
*Common Name:**	VMXMLOFNEQBYHM-INVHITAPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VMXMLOFNEQBYHM-INVHITAPSA-N
Standard InCHI:	InChI=1S/C27H42O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h6-7,11,17-18,20-24,28H,8-10,12-16H2,1-5H3/b11-6+/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1
SMILES:	CC(C)C(=O)/C=C/[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3356400
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids [CHEMONTID:0001469] Cholesterols and derivatives

*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
NPO22674	Caulerpa racemosa	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23548547]
NPO22674	Caulerpa racemosa	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25497963]
NPO22674	Caulerpa racemosa	Species	Caulerpaceae	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	3
Others	6

Activity Type	# Activity
Cell Line	2
Individual Protein	6
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1210	Individual Protein	T-cell protein-tyrosine phosphatase	Homo sapiens	Inhibition	<	50.0	%	PMID[486891]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	49970.0	nM	PMID[486891]
NPT205	Individual Protein	Protein-tyrosine phosphatase 1C	Homo sapiens	Inhibition	<	50.0	%	PMID[486891]
NPT206	Individual Protein	Protein-tyrosine phosphatase 2C	Homo sapiens	Inhibition	<	50.0	%	PMID[486891]
NPT1870	Individual Protein	Receptor-type tyrosine-protein phosphatase F (LAR)	Homo sapiens	Inhibition	<	50.0	%	PMID[486891]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	15.98	%	PMID[486891]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[486891]
NPT911	Individual Protein	Dual specificity phosphatase Cdc25B	Homo sapiens	Inhibition	<	50.0	%	PMID[486891]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[486891]

☑ 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 NPC33913 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	153
0.1-0.2	1014
0.2-0.3	5186
0.3-0.4	15548
0.4-0.5	7674
0.5-0.6	6385
0.6-0.7	4604
0.7-0.8	1797
0.8-0.85	213
0.85-0.9	104
0.9-0.95	17
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9747	High Similarity	NPC472265
0.939	High Similarity	NPC58063
0.9268	High Similarity	NPC474733
0.9268	High Similarity	NPC145879
0.9268	High Similarity	NPC474732
0.9268	High Similarity	NPC474778
0.9268	High Similarity	NPC31564
0.9157	High Similarity	NPC475740
0.9125	High Similarity	NPC6434
0.9036	High Similarity	NPC118648
0.9036	High Similarity	NPC222613
0.9036	High Similarity	NPC475022
0.9024	High Similarity	NPC59453
0.9024	High Similarity	NPC214043
0.9024	High Similarity	NPC85774
0.9024	High Similarity	NPC221758
0.8974	High Similarity	NPC113733
0.8974	High Similarity	NPC321381
0.8974	High Similarity	NPC107059
0.8974	High Similarity	NPC321016
0.8953	High Similarity	NPC272746
0.8941	High Similarity	NPC26959
0.8941	High Similarity	NPC186688
0.8941	High Similarity	NPC146554
0.8941	High Similarity	NPC1015
0.8941	High Similarity	NPC268406
0.8941	High Similarity	NPC31985
0.8929	High Similarity	NPC93778
0.8916	High Similarity	NPC22133
0.8916	High Similarity	NPC469948
0.8861	High Similarity	NPC318495
0.8861	High Similarity	NPC155986
0.8861	High Similarity	NPC198968
0.8851	High Similarity	NPC474736
0.8846	High Similarity	NPC288035
0.8846	High Similarity	NPC304309
0.8846	High Similarity	NPC28657
0.8846	High Similarity	NPC162742
0.8846	High Similarity	NPC136188
0.8846	High Similarity	NPC230301
0.8846	High Similarity	NPC22105
0.8846	High Similarity	NPC285893
0.8846	High Similarity	NPC134847
0.8837	High Similarity	NPC48010
0.8824	High Similarity	NPC471722
0.881	High Similarity	NPC51014
0.8795	High Similarity	NPC473246
0.878	High Similarity	NPC151519
0.8765	High Similarity	NPC241290
0.8765	High Similarity	NPC209944
0.8765	High Similarity	NPC234193
0.8765	High Similarity	NPC164840
0.875	High Similarity	NPC18603
0.875	High Similarity	NPC307965
0.875	High Similarity	NPC76931
0.875	High Similarity	NPC474216
0.875	High Similarity	NPC477522
0.875	High Similarity	NPC87604
0.875	High Similarity	NPC473943
0.8736	High Similarity	NPC475806
0.8734	High Similarity	NPC300324
0.8734	High Similarity	NPC240604
0.8734	High Similarity	NPC134330
0.8734	High Similarity	NPC129165
0.8721	High Similarity	NPC119416
0.8721	High Similarity	NPC472240
0.8721	High Similarity	NPC473999
0.8721	High Similarity	NPC309603
0.8721	High Similarity	NPC262858
0.8706	High Similarity	NPC475772
0.8706	High Similarity	NPC89747
0.869	High Similarity	NPC470574
0.8667	High Similarity	NPC108078
0.8659	High Similarity	NPC47761
0.8659	High Similarity	NPC264245
0.8642	High Similarity	NPC47982
0.8642	High Similarity	NPC143182
0.8642	High Similarity	NPC84694
0.8642	High Similarity	NPC81306
0.8642	High Similarity	NPC109546
0.8642	High Similarity	NPC328714
0.8642	High Similarity	NPC28862
0.8625	High Similarity	NPC34019
0.8621	High Similarity	NPC85173
0.8621	High Similarity	NPC126993
0.8621	High Similarity	NPC191684
0.8608	High Similarity	NPC141071
0.8608	High Similarity	NPC257347
0.8608	High Similarity	NPC471723
0.8605	High Similarity	NPC328313
0.8605	High Similarity	NPC328539
0.859	High Similarity	NPC471799
0.8588	High Similarity	NPC155011
0.8588	High Similarity	NPC72133
0.8571	High Similarity	NPC237712
0.8571	High Similarity	NPC321187
0.8571	High Similarity	NPC329043
0.8571	High Similarity	NPC82902
0.8571	High Similarity	NPC161423
0.8571	High Similarity	NPC227064
0.8571	High Similarity	NPC58841
0.8554	High Similarity	NPC50964
0.8554	High Similarity	NPC49964
0.8539	High Similarity	NPC196485
0.8539	High Similarity	NPC245972
0.8539	High Similarity	NPC8993
0.8537	High Similarity	NPC472478
0.8537	High Similarity	NPC2482
0.8537	High Similarity	NPC26117
0.8523	High Similarity	NPC131872
0.8523	High Similarity	NPC473998
0.8519	High Similarity	NPC275910
0.8506	High Similarity	NPC32830
0.8506	High Similarity	NPC76879
0.8506	High Similarity	NPC474245
0.8506	High Similarity	NPC86319
0.8506	High Similarity	NPC275740
0.8506	High Similarity	NPC477943
0.85	High Similarity	NPC96319
0.85	High Similarity	NPC470362
0.85	High Similarity	NPC189883
0.8488	Intermediate Similarity	NPC141292
0.8488	Intermediate Similarity	NPC136548
0.8481	Intermediate Similarity	NPC471797
0.8471	Intermediate Similarity	NPC29447
0.8471	Intermediate Similarity	NPC471224
0.8471	Intermediate Similarity	NPC474218
0.8452	Intermediate Similarity	NPC476082
0.8452	Intermediate Similarity	NPC278648
0.8434	Intermediate Similarity	NPC209620
0.8434	Intermediate Similarity	NPC82986
0.8434	Intermediate Similarity	NPC23852
0.8434	Intermediate Similarity	NPC474759
0.8434	Intermediate Similarity	NPC474531
0.8434	Intermediate Similarity	NPC470383
0.8434	Intermediate Similarity	NPC474683
0.8434	Intermediate Similarity	NPC474752
0.8434	Intermediate Similarity	NPC7505
0.8434	Intermediate Similarity	NPC474731
0.8427	Intermediate Similarity	NPC475255
0.8427	Intermediate Similarity	NPC470923
0.8427	Intermediate Similarity	NPC134826
0.8427	Intermediate Similarity	NPC12722
0.8427	Intermediate Similarity	NPC474807
0.8427	Intermediate Similarity	NPC109305
0.8427	Intermediate Similarity	NPC250575
0.8415	Intermediate Similarity	NPC1319
0.8415	Intermediate Similarity	NPC30986
0.8415	Intermediate Similarity	NPC209430
0.8395	Intermediate Similarity	NPC214570
0.8391	Intermediate Similarity	NPC143767
0.8391	Intermediate Similarity	NPC53911
0.8391	Intermediate Similarity	NPC474677
0.8391	Intermediate Similarity	NPC292491
0.8391	Intermediate Similarity	NPC471724
0.8391	Intermediate Similarity	NPC131470
0.8391	Intermediate Similarity	NPC310752
0.8372	Intermediate Similarity	NPC94666
0.8372	Intermediate Similarity	NPC327115
0.8372	Intermediate Similarity	NPC20688
0.8372	Intermediate Similarity	NPC469994
0.8372	Intermediate Similarity	NPC474970
0.837	Intermediate Similarity	NPC103051
0.837	Intermediate Similarity	NPC114274
0.8354	Intermediate Similarity	NPC474140
0.8353	Intermediate Similarity	NPC205845
0.8333	Intermediate Similarity	NPC189972
0.8333	Intermediate Similarity	NPC470614
0.8333	Intermediate Similarity	NPC279410
0.8333	Intermediate Similarity	NPC101462
0.8333	Intermediate Similarity	NPC1272
0.8333	Intermediate Similarity	NPC476186
0.8333	Intermediate Similarity	NPC5985
0.8333	Intermediate Similarity	NPC111015
0.8333	Intermediate Similarity	NPC119562
0.8315	Intermediate Similarity	NPC185936
0.8315	Intermediate Similarity	NPC110923
0.8315	Intermediate Similarity	NPC74296
0.8315	Intermediate Similarity	NPC212948
0.8315	Intermediate Similarity	NPC168027
0.8313	Intermediate Similarity	NPC236112
0.8295	Intermediate Similarity	NPC2983
0.8295	Intermediate Similarity	NPC177141
0.8293	Intermediate Similarity	NPC167037
0.8293	Intermediate Similarity	NPC244385
0.8293	Intermediate Similarity	NPC285761
0.8293	Intermediate Similarity	NPC82635
0.8293	Intermediate Similarity	NPC477514
0.8293	Intermediate Similarity	NPC6978
0.8293	Intermediate Similarity	NPC138621
0.8276	Intermediate Similarity	NPC474684
0.8276	Intermediate Similarity	NPC317590
0.8276	Intermediate Similarity	NPC90652
0.8276	Intermediate Similarity	NPC142361
0.8272	Intermediate Similarity	NPC237460
0.8272	Intermediate Similarity	NPC202642
0.8272	Intermediate Similarity	NPC247325
0.8272	Intermediate Similarity	NPC244488
0.8272	Intermediate Similarity	NPC73875
0.8272	Intermediate Similarity	NPC46160

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 NPC33913 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	1255
0.2-0.3	4224
0.3-0.4	2510
0.4-0.5	548
0.5-0.6	165
0.6-0.7	120
0.7-0.8	146
0.8-0.85	32
0.85-0.9	11
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9024	High Similarity	NPD4786	Approved
0.8953	High Similarity	NPD6079	Approved
0.8846	High Similarity	NPD6942	Approved
0.8846	High Similarity	NPD7339	Approved
0.878	High Similarity	NPD3667	Approved
0.8721	High Similarity	NPD5328	Approved
0.8642	High Similarity	NPD4195	Approved
0.8588	High Similarity	NPD3618	Phase 1
0.8571	High Similarity	NPD3666	Approved
0.8571	High Similarity	NPD3665	Phase 1
0.8571	High Similarity	NPD3133	Approved
0.85	High Similarity	NPD3701	Clinical (unspecified phase)
0.8352	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8352	Intermediate Similarity	NPD5221	Approved
0.8352	Intermediate Similarity	NPD5222	Approved
0.8261	Intermediate Similarity	NPD5173	Approved
0.8222	Intermediate Similarity	NPD4202	Approved
0.8161	Intermediate Similarity	NPD5279	Phase 3
0.8118	Intermediate Similarity	NPD4221	Approved
0.8118	Intermediate Similarity	NPD4223	Phase 3
0.8095	Intermediate Similarity	NPD7525	Registered
0.809	Intermediate Similarity	NPD4753	Phase 2
0.8085	Intermediate Similarity	NPD5286	Approved
0.8085	Intermediate Similarity	NPD4696	Approved
0.8085	Intermediate Similarity	NPD5285	Approved
0.8046	Intermediate Similarity	NPD5329	Approved
0.8043	Intermediate Similarity	NPD5210	Approved
0.8043	Intermediate Similarity	NPD4629	Approved
0.8025	Intermediate Similarity	NPD6924	Approved
0.8025	Intermediate Similarity	NPD4784	Approved
0.8025	Intermediate Similarity	NPD6926	Approved
0.8025	Intermediate Similarity	NPD4785	Approved
0.8022	Intermediate Similarity	NPD6399	Phase 3
0.8	Intermediate Similarity	NPD7152	Approved
0.8	Intermediate Similarity	NPD7150	Approved
0.8	Intermediate Similarity	NPD5223	Approved
0.8	Intermediate Similarity	NPD7151	Approved
0.7957	Intermediate Similarity	NPD4697	Phase 3
0.7955	Intermediate Similarity	NPD5690	Phase 2
0.7931	Intermediate Similarity	NPD4197	Approved
0.7931	Intermediate Similarity	NPD3668	Phase 3
0.7917	Intermediate Similarity	NPD5224	Approved
0.7917	Intermediate Similarity	NPD5226	Approved
0.7917	Intermediate Similarity	NPD5225	Approved
0.7917	Intermediate Similarity	NPD4633	Approved
0.7917	Intermediate Similarity	NPD5211	Phase 2
0.7875	Intermediate Similarity	NPD7144	Approved
0.7875	Intermediate Similarity	NPD7143	Approved
0.7872	Intermediate Similarity	NPD4755	Approved
0.7835	Intermediate Similarity	NPD5175	Approved
0.7835	Intermediate Similarity	NPD5174	Approved
0.7831	Intermediate Similarity	NPD6933	Approved
0.7816	Intermediate Similarity	NPD4788	Approved
0.7789	Intermediate Similarity	NPD5290	Discontinued
0.7778	Intermediate Similarity	NPD4243	Approved
0.7755	Intermediate Similarity	NPD5141	Approved
0.7753	Intermediate Similarity	NPD4690	Approved
0.7753	Intermediate Similarity	NPD7146	Approved
0.7753	Intermediate Similarity	NPD5205	Approved
0.7753	Intermediate Similarity	NPD5330	Approved
0.7753	Intermediate Similarity	NPD7334	Approved
0.7753	Intermediate Similarity	NPD4138	Approved
0.7753	Intermediate Similarity	NPD4689	Approved
0.7753	Intermediate Similarity	NPD4693	Phase 3
0.7753	Intermediate Similarity	NPD4688	Approved
0.7753	Intermediate Similarity	NPD6409	Approved
0.7753	Intermediate Similarity	NPD6684	Approved
0.7753	Intermediate Similarity	NPD7521	Approved
0.775	Intermediate Similarity	NPD6923	Approved
0.775	Intermediate Similarity	NPD6922	Approved
0.7717	Intermediate Similarity	NPD7515	Phase 2
0.7708	Intermediate Similarity	NPD4700	Approved
0.77	Intermediate Similarity	NPD6881	Approved
0.77	Intermediate Similarity	NPD6899	Approved
0.7684	Intermediate Similarity	NPD6084	Phase 2
0.7684	Intermediate Similarity	NPD6083	Phase 2
0.7674	Intermediate Similarity	NPD4695	Discontinued
0.7667	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3617	Approved
0.76	Intermediate Similarity	NPD5697	Approved
0.7582	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6672	Approved
0.7582	Intermediate Similarity	NPD5737	Approved
0.7582	Intermediate Similarity	NPD6903	Approved
0.7558	Intermediate Similarity	NPD7645	Phase 2
0.7558	Intermediate Similarity	NPD6929	Approved
0.7556	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD5280	Approved
0.7556	Intermediate Similarity	NPD4694	Approved
0.7549	Intermediate Similarity	NPD7290	Approved
0.7549	Intermediate Similarity	NPD6883	Approved
0.7549	Intermediate Similarity	NPD7102	Approved
0.7529	Intermediate Similarity	NPD6932	Approved
0.7525	Intermediate Similarity	NPD4730	Approved
0.7525	Intermediate Similarity	NPD6011	Approved
0.7525	Intermediate Similarity	NPD5168	Approved
0.7525	Intermediate Similarity	NPD4729	Approved
0.75	Intermediate Similarity	NPD5739	Approved
0.75	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD6402	Approved
0.7476	Intermediate Similarity	NPD6650	Approved
0.7476	Intermediate Similarity	NPD6617	Approved
0.7476	Intermediate Similarity	NPD6869	Approved
0.7476	Intermediate Similarity	NPD6649	Approved
0.7476	Intermediate Similarity	NPD6847	Approved
0.7476	Intermediate Similarity	NPD8130	Phase 1
0.7475	Intermediate Similarity	NPD4754	Approved
0.7471	Intermediate Similarity	NPD6930	Phase 2
0.7471	Intermediate Similarity	NPD6931	Approved
0.7471	Intermediate Similarity	NPD4748	Discontinued
0.7451	Intermediate Similarity	NPD6012	Approved
0.7451	Intermediate Similarity	NPD6013	Approved
0.7451	Intermediate Similarity	NPD6014	Approved
0.7444	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7145	Approved
0.7439	Intermediate Similarity	NPD4691	Approved
0.7439	Intermediate Similarity	NPD4747	Approved
0.7423	Intermediate Similarity	NPD7638	Approved
0.7404	Intermediate Similarity	NPD8297	Approved
0.7404	Intermediate Similarity	NPD6882	Approved
0.7381	Intermediate Similarity	NPD4058	Approved
0.7379	Intermediate Similarity	NPD5251	Approved
0.7379	Intermediate Similarity	NPD5247	Approved
0.7379	Intermediate Similarity	NPD5249	Phase 3
0.7379	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5248	Approved
0.7379	Intermediate Similarity	NPD5135	Approved
0.7379	Intermediate Similarity	NPD5169	Approved
0.7379	Intermediate Similarity	NPD5250	Approved
0.7379	Intermediate Similarity	NPD4634	Approved
0.7368	Intermediate Similarity	NPD7748	Approved
0.7363	Intermediate Similarity	NPD4623	Approved
0.7363	Intermediate Similarity	NPD4519	Discontinued
0.7353	Intermediate Similarity	NPD5128	Approved
0.7353	Intermediate Similarity	NPD7320	Approved
0.7347	Intermediate Similarity	NPD7640	Approved
0.7347	Intermediate Similarity	NPD7639	Approved
0.734	Intermediate Similarity	NPD5284	Approved
0.734	Intermediate Similarity	NPD5281	Approved
0.7327	Intermediate Similarity	NPD4768	Approved
0.7327	Intermediate Similarity	NPD4767	Approved
0.7326	Intermediate Similarity	NPD5776	Phase 2
0.7326	Intermediate Similarity	NPD6925	Approved
0.7317	Intermediate Similarity	NPD4137	Phase 3
0.7308	Intermediate Similarity	NPD5216	Approved
0.7308	Intermediate Similarity	NPD5215	Approved
0.7308	Intermediate Similarity	NPD5217	Approved
0.7308	Intermediate Similarity	NPD5127	Approved
0.7294	Intermediate Similarity	NPD4190	Phase 3
0.7294	Intermediate Similarity	NPD5275	Approved
0.7292	Intermediate Similarity	NPD5695	Phase 3
0.729	Intermediate Similarity	NPD7115	Discovery
0.7282	Intermediate Similarity	NPD6373	Approved
0.7282	Intermediate Similarity	NPD6372	Approved
0.7273	Intermediate Similarity	NPD7509	Discontinued
0.7273	Intermediate Similarity	NPD7514	Phase 3
0.7255	Intermediate Similarity	NPD5701	Approved
0.7245	Intermediate Similarity	NPD5696	Approved
0.7241	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6695	Phase 3
0.7204	Intermediate Similarity	NPD4518	Approved
0.7196	Intermediate Similarity	NPD6868	Approved
0.7191	Intermediate Similarity	NPD6902	Approved
0.7176	Intermediate Similarity	NPD4687	Approved
0.7176	Intermediate Similarity	NPD5733	Approved
0.717	Intermediate Similarity	NPD4632	Approved
0.7159	Intermediate Similarity	NPD6683	Phase 2
0.7143	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7902	Approved
0.7143	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6673	Approved
0.7128	Intermediate Similarity	NPD6904	Approved
0.7128	Intermediate Similarity	NPD6080	Approved
0.7103	Intermediate Similarity	NPD5167	Approved
0.7093	Intermediate Similarity	NPD8264	Approved
0.7087	Intermediate Similarity	NPD6412	Phase 2
0.7079	Intermediate Similarity	NPD7332	Phase 2
0.7079	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6893	Approved
0.7064	Intermediate Similarity	NPD6335	Approved
0.7053	Intermediate Similarity	NPD4096	Approved
0.703	Intermediate Similarity	NPD5091	Approved
0.7021	Intermediate Similarity	NPD5208	Approved
0.7	Intermediate Similarity	NPD4692	Approved
0.7	Intermediate Similarity	NPD7100	Approved
0.7	Intermediate Similarity	NPD7101	Approved
0.7	Intermediate Similarity	NPD4139	Approved
0.6989	Remote Similarity	NPD6098	Approved
0.6979	Remote Similarity	NPD7637	Suspended
0.6972	Remote Similarity	NPD6009	Approved
0.6972	Remote Similarity	NPD6317	Approved
0.6947	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6051	Approved
0.6941	Remote Similarity	NPD5276	Approved
0.6939	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6054	Approved
0.6915	Remote Similarity	NPD7524	Approved

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