NPASS Compound

Structure

NPC469880 OpenBabel07101718242D 53 53 0 0 1 0 0 0 0 0999 V2000 -1.4603 4.1809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4507 -2.3129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8037 1.3748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4641 4.0937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0415 3.1874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6585 -4.5566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5414 -9.5979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7559 -7.3471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6321 -9.2559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7716 -3.5566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5566 1.6585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6585 -3.5566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6151 2.3682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4811 -9.2559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1131 -8.1131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5566 -9.7716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2559 -6.4811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5718 -9.5979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7716 -4.5566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4848 -5.5414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7660 -8.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5979 -2.5718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5414 1.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5566 1.6585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1428 -1.6321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6428 -7.3471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7559 -0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3471 0.6428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6321 1.1428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4848 -2.5718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1925 1.4619 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -7.3471 -8.7559 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.5566 -9.7716 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -9.5979 -5.5414 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.1428 -6.4811 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -8.1131 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2559 -1.6321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4811 1.1428 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5718 1.4848 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -8.1131 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7660 0.6428 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6428 -0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9207 -9.5751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4694 -10.7678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5639 -5.8002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0491 -6.9037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -8.8202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1622 -1.2095 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9037 2.0491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3129 2.4507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8202 0.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4619 -0.1925 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 4 1 0 0 0 0 2 30 1 0 0 0 0 3 31 1 0 0 0 0 4 5 1 0 0 0 0 5 13 1 0 0 0 0 6 12 1 0 0 0 0 6 20 1 0 0 0 0 7 14 1 0 0 0 0 7 16 1 0 0 0 0 8 15 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 9 21 1 0 0 0 0 10 19 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 11 24 1 0 0 0 0 12 30 1 0 0 0 0 13 31 1 0 0 0 0 14 32 1 0 0 0 0 15 32 1 0 0 0 0 16 33 1 0 0 0 0 17 34 1 0 0 0 0 18 33 1 0 0 0 0 19 34 1 0 0 0 0 20 35 1 0 0 0 0 21 36 1 0 0 0 0 22 37 1 0 0 0 0 23 38 1 0 0 0 0 24 39 1 0 0 0 0 25 30 2 0 0 0 0 25 42 1 0 0 0 0 26 35 1 0 0 0 0 26 36 1 0 0 0 0 27 37 1 0 0 0 0 27 40 1 0 0 0 0 28 38 1 0 0 0 0 28 40 1 0 0 0 0 29 39 1 0 0 0 0 29 41 1 0 0 0 0 31 41 1 0 0 0 0 32 43 1 0 0 0 0 33 44 1 0 0 0 0 34 45 1 0 0 0 0 35 46 1 6 0 0 0 36 47 1 6 0 0 0 37 48 1 6 0 0 0 38 49 1 1 0 0 0 39 50 1 0 0 0 0 40 51 1 6 0 0 0 41 53 1 0 0 0 0 42 52 2 0 0 0 0 42 53 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	760.57
Volume:	817.851
LogP:	4.146
LogD:	3.121
LogS:	-5.223
# Rotatable Bonds:	4
TPSA:	208.37
# H-Bond Aceptor:	11
# H-Bond Donor:	9
# Rings:	1
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.129
Synthetic Accessibility Score:	5.67
Fsp3:	0.929
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.747
MDCK Permeability:	8.424123370787129e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.687
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	67.68000030517578%
Volume Distribution (VD):	0.849
Pgp-substrate:	5.9955878257751465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.009
CYP3A4-inhibitor:	0.321
CYP3A4-substrate:	0.056

ADMET: Excretion

Clearance (CL):	10.799
Half-life (T1/2):	0.705

ADMET: Toxicity

hERG Blockers:	0.156
Human Hepatotoxicity (H-HT):	0.599
Drug-inuced Liver Injury (DILI):	0.0
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.984
Carcinogencity:	0.198
Eye Corrosion:	0.003
Eye Irritation:	0.038
Respiratory Toxicity:	0.583

Download Data

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

Natural Product: NPC469880

Natural Product ID:	NPC469880
*Common Name:**	Caylobolide B
IUPAC Name:	(3E,8S,10R,26S,28S,30S)-36-hexan-2-yl-8,10,14,18,22,26,28,30,34-nonahydroxy-4-methyl-1-oxacyclohexatriacont-3-en-2-one
Synonyms:
Standard InCHIKey:	XCMPEWXFVPCAPO-UHFHEBRASA-N
Standard InCHI:	InChI=1S/C42H80O11/c1-4-5-13-31(3)41-29-39(50)24-11-23-38(49)28-40(51)27-37(48)22-10-19-34(45)17-8-15-32(43)14-7-16-33(44)18-9-21-36(47)26-35(46)20-6-12-30(2)25-42(52)53-41/h25,31-41,43-51H,4-24,26-29H2,1-3H3/b30-25+/t31?,32?,33?,34?,35-,36+,37-,38-,39?,40-,41?/m0/s1
SMILES:	CCCCC(C)C1CC(CCCC(CC(CC(CCCC(CCCC(CCCC(CCCC(CC(CCCC(=CC(=O)O1)C)O)O)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224775
PubChem CID:	46938851
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO32448	phormidium sp.	Species	Oscillatoriaceae	Bacteria	n.a.	Florida	n.a.	PMID[20806908]

☑ 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

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	4500.0	nM	PMID[522928]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	12200.0	nM	PMID[522928]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	9900.0	nM	PMID[522928]

☑ 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 NPC469880 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	184
0.1-0.2	1335
0.2-0.3	5155
0.3-0.4	14207
0.4-0.5	10914
0.5-0.6	7084
0.6-0.7	3218
0.7-0.8	566
0.8-0.85	18
0.85-0.9	7
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9444	High Similarity	NPC477202
0.9315	High Similarity	NPC477203
0.9079	High Similarity	NPC184208
0.9079	High Similarity	NPC8538
0.9079	High Similarity	NPC315731
0.8873	High Similarity	NPC101622
0.8816	High Similarity	NPC139712
0.8767	High Similarity	NPC477085
0.875	High Similarity	NPC4299
0.8649	High Similarity	NPC477204
0.863	High Similarity	NPC477087
0.863	High Similarity	NPC477086
0.8553	High Similarity	NPC84360
0.8519	High Similarity	NPC47220
0.8519	High Similarity	NPC186332
0.8415	Intermediate Similarity	NPC199382
0.8333	Intermediate Similarity	NPC477088
0.8333	Intermediate Similarity	NPC472266
0.8289	Intermediate Similarity	NPC327041
0.8289	Intermediate Similarity	NPC285840
0.8272	Intermediate Similarity	NPC160517
0.8272	Intermediate Similarity	NPC78673
0.8272	Intermediate Similarity	NPC186155
0.8235	Intermediate Similarity	NPC114172
0.8235	Intermediate Similarity	NPC476084
0.8235	Intermediate Similarity	NPC206679
0.8235	Intermediate Similarity	NPC476075
0.8235	Intermediate Similarity	NPC471324
0.8171	Intermediate Similarity	NPC242233
0.8171	Intermediate Similarity	NPC471494
0.814	Intermediate Similarity	NPC472196
0.814	Intermediate Similarity	NPC238090
0.814	Intermediate Similarity	NPC472195
0.814	Intermediate Similarity	NPC109406
0.814	Intermediate Similarity	NPC159092
0.8133	Intermediate Similarity	NPC477084
0.8133	Intermediate Similarity	NPC472254
0.8125	Intermediate Similarity	NPC112868
0.8125	Intermediate Similarity	NPC475944
0.8118	Intermediate Similarity	NPC177668
0.8108	Intermediate Similarity	NPC269841
0.8101	Intermediate Similarity	NPC55304
0.8101	Intermediate Similarity	NPC86971
0.8101	Intermediate Similarity	NPC226226
0.8077	Intermediate Similarity	NPC315394
0.8072	Intermediate Similarity	NPC61527
0.8072	Intermediate Similarity	NPC311163
0.8046	Intermediate Similarity	NPC159698
0.8026	Intermediate Similarity	NPC329890
0.8026	Intermediate Similarity	NPC327383
0.8026	Intermediate Similarity	NPC329914
0.8026	Intermediate Similarity	NPC185186
0.8025	Intermediate Similarity	NPC123908
0.8025	Intermediate Similarity	NPC10080
0.8	Intermediate Similarity	NPC469660
0.8	Intermediate Similarity	NPC133450
0.7976	Intermediate Similarity	NPC316138
0.7976	Intermediate Similarity	NPC313658
0.7975	Intermediate Similarity	NPC209135
0.7975	Intermediate Similarity	NPC474816
0.7955	Intermediate Similarity	NPC300710
0.7927	Intermediate Similarity	NPC231601
0.7927	Intermediate Similarity	NPC116543
0.7927	Intermediate Similarity	NPC474809
0.7907	Intermediate Similarity	NPC473448
0.7907	Intermediate Similarity	NPC3952
0.7901	Intermediate Similarity	NPC474894
0.7895	Intermediate Similarity	NPC316185
0.7875	Intermediate Similarity	NPC325869
0.7875	Intermediate Similarity	NPC471537
0.7865	Intermediate Similarity	NPC255410
0.7865	Intermediate Similarity	NPC173329
0.7865	Intermediate Similarity	NPC288350
0.7857	Intermediate Similarity	NPC469483
0.7857	Intermediate Similarity	NPC164393
0.7848	Intermediate Similarity	NPC262747
0.7841	Intermediate Similarity	NPC256368
0.7838	Intermediate Similarity	NPC193029
0.7838	Intermediate Similarity	NPC473357
0.7821	Intermediate Similarity	NPC329852
0.7805	Intermediate Similarity	NPC471298
0.7778	Intermediate Similarity	NPC470147
0.7778	Intermediate Similarity	NPC133226
0.7778	Intermediate Similarity	NPC120299
0.7778	Intermediate Similarity	NPC475332
0.7765	Intermediate Similarity	NPC477959
0.7763	Intermediate Similarity	NPC476037
0.7763	Intermediate Similarity	NPC329904
0.7763	Intermediate Similarity	NPC473361
0.7763	Intermediate Similarity	NPC476012
0.7738	Intermediate Similarity	NPC137033
0.7738	Intermediate Similarity	NPC477014
0.7738	Intermediate Similarity	NPC477013
0.7722	Intermediate Similarity	NPC188860
0.7711	Intermediate Similarity	NPC11620
0.7711	Intermediate Similarity	NPC471297
0.7711	Intermediate Similarity	NPC311070
0.7701	Intermediate Similarity	NPC202886
0.7692	Intermediate Similarity	NPC315843
0.7692	Intermediate Similarity	NPC475653
0.7692	Intermediate Similarity	NPC474758
0.7692	Intermediate Similarity	NPC107654
0.7674	Intermediate Similarity	NPC227379
0.7674	Intermediate Similarity	NPC474471
0.7667	Intermediate Similarity	NPC472995
0.7654	Intermediate Similarity	NPC470148
0.7654	Intermediate Similarity	NPC321728
0.7654	Intermediate Similarity	NPC470149
0.7654	Intermediate Similarity	NPC180725
0.7647	Intermediate Similarity	NPC122502
0.7647	Intermediate Similarity	NPC305475
0.7647	Intermediate Similarity	NPC477015
0.7647	Intermediate Similarity	NPC475461
0.7647	Intermediate Similarity	NPC131813
0.764	Intermediate Similarity	NPC474247
0.7632	Intermediate Similarity	NPC151481
0.7625	Intermediate Similarity	NPC40049
0.7625	Intermediate Similarity	NPC474026
0.7625	Intermediate Similarity	NPC233071
0.7625	Intermediate Similarity	NPC476439
0.7619	Intermediate Similarity	NPC266718
0.7619	Intermediate Similarity	NPC474776
0.7619	Intermediate Similarity	NPC163093
0.7614	Intermediate Similarity	NPC158061
0.76	Intermediate Similarity	NPC259299
0.759	Intermediate Similarity	NPC65930
0.759	Intermediate Similarity	NPC180363
0.759	Intermediate Similarity	NPC475159
0.759	Intermediate Similarity	NPC323251
0.759	Intermediate Similarity	NPC131002
0.759	Intermediate Similarity	NPC473712
0.759	Intermediate Similarity	NPC473529
0.759	Intermediate Similarity	NPC474291
0.759	Intermediate Similarity	NPC73310
0.759	Intermediate Similarity	NPC145914
0.759	Intermediate Similarity	NPC94875
0.759	Intermediate Similarity	NPC329829
0.759	Intermediate Similarity	NPC11332
0.759	Intermediate Similarity	NPC473780
0.7586	Intermediate Similarity	NPC295312
0.7586	Intermediate Similarity	NPC477748
0.7568	Intermediate Similarity	NPC282760
0.7564	Intermediate Similarity	NPC222244
0.7564	Intermediate Similarity	NPC16349
0.7561	Intermediate Similarity	NPC474739
0.7558	Intermediate Similarity	NPC86005
0.7558	Intermediate Similarity	NPC178215
0.7558	Intermediate Similarity	NPC471796
0.7558	Intermediate Similarity	NPC248602
0.7556	Intermediate Similarity	NPC36954
0.7556	Intermediate Similarity	NPC276110
0.7534	Intermediate Similarity	NPC217940
0.7532	Intermediate Similarity	NPC64234
0.7532	Intermediate Similarity	NPC37929
0.7531	Intermediate Similarity	NPC108816
0.7531	Intermediate Similarity	NPC93763
0.7531	Intermediate Similarity	NPC248775
0.7531	Intermediate Similarity	NPC3852
0.7529	Intermediate Similarity	NPC471567
0.7529	Intermediate Similarity	NPC120398
0.7529	Intermediate Similarity	NPC261380
0.7529	Intermediate Similarity	NPC329615
0.7529	Intermediate Similarity	NPC329838
0.7529	Intermediate Similarity	NPC11804
0.7529	Intermediate Similarity	NPC67081
0.7529	Intermediate Similarity	NPC255307
0.7529	Intermediate Similarity	NPC471223
0.7528	Intermediate Similarity	NPC320089
0.7528	Intermediate Similarity	NPC475838
0.7528	Intermediate Similarity	NPC125674
0.7528	Intermediate Similarity	NPC228451
0.7528	Intermediate Similarity	NPC476300
0.75	Intermediate Similarity	NPC40746
0.75	Intermediate Similarity	NPC16488
0.75	Intermediate Similarity	NPC170377
0.75	Intermediate Similarity	NPC161045
0.75	Intermediate Similarity	NPC78973
0.75	Intermediate Similarity	NPC313670
0.75	Intermediate Similarity	NPC476004
0.75	Intermediate Similarity	NPC301525
0.75	Intermediate Similarity	NPC474761
0.75	Intermediate Similarity	NPC44261
0.75	Intermediate Similarity	NPC69469
0.75	Intermediate Similarity	NPC203627
0.75	Intermediate Similarity	NPC169575
0.75	Intermediate Similarity	NPC144415
0.75	Intermediate Similarity	NPC276290
0.75	Intermediate Similarity	NPC310210
0.75	Intermediate Similarity	NPC42476
0.75	Intermediate Similarity	NPC23748
0.75	Intermediate Similarity	NPC305698
0.75	Intermediate Similarity	NPC253801
0.75	Intermediate Similarity	NPC472377
0.75	Intermediate Similarity	NPC161855
0.75	Intermediate Similarity	NPC475855
0.7473	Intermediate Similarity	NPC279621
0.7473	Intermediate Similarity	NPC473291
0.7473	Intermediate Similarity	NPC472997
0.7473	Intermediate Similarity	NPC230800
0.7473	Intermediate Similarity	NPC472996

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 NPC469880 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1894
0.2-0.3	3790
0.3-0.4	2359
0.4-0.5	648
0.5-0.6	232
0.6-0.7	63
0.7-0.8	6
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD7838	Discovery
0.8118	Intermediate Similarity	NPD6698	Approved
0.8118	Intermediate Similarity	NPD46	Approved
0.7808	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7983	Approved
0.7412	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7154	Phase 3
0.7158	Intermediate Similarity	NPD5344	Discontinued
0.7143	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7638	Approved
0.7097	Intermediate Similarity	NPD7839	Suspended
0.7053	Intermediate Similarity	NPD7639	Approved
0.7053	Intermediate Similarity	NPD7640	Approved
0.697	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4251	Approved
0.6966	Remote Similarity	NPD4250	Approved
0.6957	Remote Similarity	NPD5778	Approved
0.6957	Remote Similarity	NPD5779	Approved
0.6941	Remote Similarity	NPD4820	Approved
0.6941	Remote Similarity	NPD4821	Approved
0.6941	Remote Similarity	NPD4822	Approved
0.6941	Remote Similarity	NPD4819	Approved
0.6923	Remote Similarity	NPD5785	Approved
0.6905	Remote Similarity	NPD4268	Approved
0.6905	Remote Similarity	NPD4271	Approved
0.69	Remote Similarity	NPD6686	Approved
0.6897	Remote Similarity	NPD5362	Discontinued
0.6875	Remote Similarity	NPD6648	Approved
0.6854	Remote Similarity	NPD4249	Approved
0.6848	Remote Similarity	NPD7637	Suspended
0.6782	Remote Similarity	NPD6435	Approved
0.6771	Remote Similarity	NPD4225	Approved
0.6747	Remote Similarity	NPD8039	Approved
0.6742	Remote Similarity	NPD5363	Approved
0.6706	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5332	Approved
0.6705	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD4790	Discontinued
0.6632	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6371	Approved
0.6591	Remote Similarity	NPD5209	Approved
0.6591	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4269	Approved
0.6591	Remote Similarity	NPD4270	Approved
0.6556	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5368	Approved
0.6538	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6695	Phase 3
0.6484	Remote Similarity	NPD5786	Approved
0.6477	Remote Similarity	NPD5369	Approved
0.6476	Remote Similarity	NPD6053	Discontinued
0.6452	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6101	Approved
0.6444	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD7750	Discontinued
0.64	Remote Similarity	NPD7632	Discontinued
0.6373	Remote Similarity	NPD4211	Phase 1
0.6364	Remote Similarity	NPD8294	Approved
0.6364	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4252	Approved
0.6364	Remote Similarity	NPD8377	Approved
0.6354	Remote Similarity	NPD7748	Approved
0.6333	Remote Similarity	NPD6110	Phase 1
0.633	Remote Similarity	NPD7328	Approved
0.633	Remote Similarity	NPD7327	Approved
0.6316	Remote Similarity	NPD6411	Approved
0.6306	Remote Similarity	NPD8380	Approved
0.6306	Remote Similarity	NPD8335	Approved
0.6306	Remote Similarity	NPD8379	Approved
0.6306	Remote Similarity	NPD8033	Approved
0.6306	Remote Similarity	NPD8378	Approved
0.6306	Remote Similarity	NPD8296	Approved
0.6296	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD368	Approved
0.6277	Remote Similarity	NPD1695	Approved
0.6277	Remote Similarity	NPD6051	Approved
0.6273	Remote Similarity	NPD7516	Approved
0.625	Remote Similarity	NPD6929	Approved
0.625	Remote Similarity	NPD6927	Phase 3
0.6237	Remote Similarity	NPD7524	Approved
0.6224	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5776	Phase 2
0.6207	Remote Similarity	NPD6925	Approved
0.6196	Remote Similarity	NPD1694	Approved
0.618	Remote Similarity	NPD6930	Phase 2
0.618	Remote Similarity	NPD7332	Phase 2
0.618	Remote Similarity	NPD6931	Approved
0.618	Remote Similarity	NPD7514	Phase 3
0.6173	Remote Similarity	NPD7331	Phase 2
0.6163	Remote Similarity	NPD8264	Approved
0.6162	Remote Similarity	NPD6084	Phase 2
0.6162	Remote Similarity	NPD7902	Approved
0.6162	Remote Similarity	NPD6083	Phase 2
0.6161	Remote Similarity	NPD7503	Approved
0.6146	Remote Similarity	NPD7515	Phase 2
0.6136	Remote Similarity	NPD7145	Approved
0.6133	Remote Similarity	NPD342	Phase 1
0.6125	Remote Similarity	NPD3197	Phase 1
0.6111	Remote Similarity	NPD6902	Approved
0.6105	Remote Similarity	NPD5370	Suspended
0.6091	Remote Similarity	NPD7505	Discontinued
0.6076	Remote Similarity	NPD4193	Approved
0.6076	Remote Similarity	NPD4192	Approved
0.6076	Remote Similarity	NPD4191	Approved
0.6076	Remote Similarity	NPD4194	Approved
0.6053	Remote Similarity	NPD7830	Approved
0.6053	Remote Similarity	NPD7829	Approved
0.6038	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD6932	Approved
0.6023	Remote Similarity	NPD4756	Discovery
0.602	Remote Similarity	NPD5282	Discontinued
0.6019	Remote Similarity	NPD6647	Phase 2
0.6018	Remote Similarity	NPD8517	Approved
0.6018	Remote Similarity	NPD8513	Phase 3
0.6018	Remote Similarity	NPD8515	Approved
0.6018	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD7087	Discontinued
0.5979	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5695	Phase 3
0.5957	Remote Similarity	NPD6409	Approved
0.5957	Remote Similarity	NPD6422	Discontinued
0.5957	Remote Similarity	NPD7334	Approved
0.5957	Remote Similarity	NPD5330	Approved
0.5957	Remote Similarity	NPD6684	Approved
0.5957	Remote Similarity	NPD7146	Approved
0.5957	Remote Similarity	NPD7521	Approved
0.5948	Remote Similarity	NPD7507	Approved
0.5946	Remote Similarity	NPD7115	Discovery
0.5934	Remote Similarity	NPD6898	Phase 1
0.593	Remote Similarity	NPD4732	Discontinued
0.5926	Remote Similarity	NPD7909	Approved
0.5918	Remote Similarity	NPD6399	Phase 3
0.5905	Remote Similarity	NPD5739	Approved
0.5905	Remote Similarity	NPD7128	Approved
0.5905	Remote Similarity	NPD6402	Approved
0.5905	Remote Similarity	NPD6675	Approved
0.5889	Remote Similarity	NPD6683	Phase 2
0.5889	Remote Similarity	NPD7645	Phase 2
0.5888	Remote Similarity	NPD6373	Approved
0.5888	Remote Similarity	NPD6372	Approved
0.5877	Remote Similarity	NPD8444	Approved
0.5872	Remote Similarity	NPD8297	Approved
0.5862	Remote Similarity	NPD6926	Approved
0.5862	Remote Similarity	NPD6924	Approved
0.5859	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7900	Approved
0.5854	Remote Similarity	NPD7341	Phase 2
0.5851	Remote Similarity	NPD6893	Approved
0.5849	Remote Similarity	NPD6685	Approved
0.5849	Remote Similarity	NPD6412	Phase 2
0.5833	Remote Similarity	NPD6903	Approved
0.5833	Remote Similarity	NPD5737	Approved
0.5833	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6672	Approved
0.5812	Remote Similarity	NPD8273	Phase 1
0.5798	Remote Similarity	NPD7319	Approved
0.5794	Remote Similarity	NPD7320	Approved
0.5794	Remote Similarity	NPD6899	Approved
0.5794	Remote Similarity	NPD6881	Approved
0.5789	Remote Similarity	NPD3195	Phase 2
0.5789	Remote Similarity	NPD4266	Approved
0.5789	Remote Similarity	NPD3196	Approved
0.5789	Remote Similarity	NPD3194	Approved
0.5784	Remote Similarity	NPD5696	Approved
0.578	Remote Similarity	NPD6650	Approved
0.578	Remote Similarity	NPD8130	Phase 1
0.578	Remote Similarity	NPD6649	Approved
0.578	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD3732	Approved
0.5776	Remote Similarity	NPD7642	Approved
0.5775	Remote Similarity	NPD4265	Approved
0.5765	Remote Similarity	NPD6923	Approved
0.5765	Remote Similarity	NPD6922	Approved
0.5763	Remote Similarity	NPD8074	Phase 3
0.5755	Remote Similarity	NPD6640	Phase 3
0.5752	Remote Similarity	NPD7641	Discontinued
0.5745	Remote Similarity	NPD3665	Phase 1
0.5745	Remote Similarity	NPD3666	Approved
0.5745	Remote Similarity	NPD3133	Approved
0.573	Remote Similarity	NPD6933	Approved
0.5727	Remote Similarity	NPD6882	Approved
0.5701	Remote Similarity	NPD5701	Approved
0.5701	Remote Similarity	NPD5697	Approved
0.5701	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD7144	Approved
0.5698	Remote Similarity	NPD7143	Approved
0.5696	Remote Similarity	NPD6109	Phase 1
0.5688	Remote Similarity	NPD7102	Approved
0.5688	Remote Similarity	NPD7290	Approved
0.5688	Remote Similarity	NPD6421	Discontinued
0.5688	Remote Similarity	NPD6883	Approved
0.5678	Remote Similarity	NPD8451	Approved
0.5676	Remote Similarity	NPD8133	Approved
0.5664	Remote Similarity	NPD7500	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