NPASS Compound

Structure

NPC182292 OpenBabel07101718182D 36 36 0 0 1 0 0 0 0 0999 V2000 0.9914 -1.1305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3320 -4.0391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4659 -3.5391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2979 -4.2979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3369 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3320 3.0391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7588 -2.8320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2979 -4.2979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5958 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8369 1.8320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2979 3.2979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4659 2.5391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2638 -4.0391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5958 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1298 2.5391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2979 3.2979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7588 1.8320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8116 6.4735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4204 5.6802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8369 -2.8320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1298 -3.5391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3369 -1.9659 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2638 3.0391 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1943 7.3974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0377 4.7563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7386 -4.3324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2608 -2.3486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1858 7.5279 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5856 8.1908 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6651 1.3486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0463 4.6258 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 -5.6465 3.9629 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 1 0 0 0 0 2 4 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 25 1 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 20 28 1 0 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 1 1 6 0 0 0 22 35 1 0 0 0 0 23 29 2 0 0 0 0 24 30 1 1 0 0 0 25 36 1 1 0 0 0 26 31 2 0 0 0 0 26 32 1 0 0 0 0 27 33 2 0 0 0 0 27 35 1 0 0 0 0 28 34 2 0 0 0 0 28 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.26
Volume:	530.881
LogP:	2.24
LogD:	1.033
LogS:	-4.439
# Rotatable Bonds:	5
TPSA:	127.2
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.424
Synthetic Accessibility Score:	4.919
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.334
MDCK Permeability:	2.8687210942734964e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.643
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.886
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	96.43342590332031%
Volume Distribution (VD):	0.295
Pgp-substrate:	2.507284164428711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.028
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.074
CYP2C9-substrate:	0.982
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.428
CYP3A4-substrate:	0.061

ADMET: Excretion

Clearance (CL):	2.221
Half-life (T1/2):	0.931

ADMET: Toxicity

hERG Blockers:	0.217
Human Hepatotoxicity (H-HT):	0.931
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.515
Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.947
Carcinogencity:	0.767
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.68

Download Data

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

Natural Product: NPC182292

Natural Product ID:	NPC182292
*Common Name:**	7-O-Succinyl Macrolactin F
IUPAC Name:	4-[[(3Z,5E,8S,9E,11Z,14S,19E,24R)-14-hydroxy-24-methyl-2,16-dioxo-1-oxacyclotetracosa-3,5,9,11,19-pentaen-8-yl]oxy]-4-oxobutanoic acid
Synonyms:	7-O-Succinyl Macrolactin F
Standard InCHIKey:	QXSCSCFGEZMIKB-AELFMCOISA-N
Standard InCHI:	InChI=1S/C28H38O8/c1-22-13-7-3-2-4-8-14-23(29)21-24(30)15-9-5-10-16-25(36-28(34)20-19-26(31)32)17-11-6-12-18-27(33)35-22/h2,4-6,9-12,16,18,22,24-25,30H,3,7-8,13-15,17,19-21H2,1H3,(H,31,32)/b4-2+,9-5-,11-6+,16-10+,18-12-/t22-,24+,25-/m1/s1
SMILES:	O=C(O[C@H]1C/C=C/C=CC(=O)O[C@H](C)CCC/C=C/CCC(=O)C[C@H](C/C=CC=C1)O)CCC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL528105
PubChem CID:	10815318
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
NPO33383	bacillus sp. sc026	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10924180]

☑ 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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	9.0	mm	PMID[522956]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	8.0	mm	PMID[522956]

☑ 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 NPC182292 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	189
0.1-0.2	1587
0.2-0.3	6736
0.3-0.4	15700
0.4-0.5	12064
0.5-0.6	4523
0.6-0.7	1566
0.7-0.8	314
0.8-0.85	14
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9315	High Similarity	NPC260396
0.8784	High Similarity	NPC284006
0.84	Intermediate Similarity	NPC293114
0.8205	Intermediate Similarity	NPC16279
0.8205	Intermediate Similarity	NPC256640
0.8205	Intermediate Similarity	NPC205615
0.8171	Intermediate Similarity	NPC16488
0.814	Intermediate Similarity	NPC473311
0.8052	Intermediate Similarity	NPC329914
0.8052	Intermediate Similarity	NPC329890
0.8026	Intermediate Similarity	NPC476012
0.8026	Intermediate Similarity	NPC476037
0.7973	Intermediate Similarity	NPC146811
0.7895	Intermediate Similarity	NPC475982
0.7895	Intermediate Similarity	NPC143396
0.7882	Intermediate Similarity	NPC315395
0.7882	Intermediate Similarity	NPC316426
0.7875	Intermediate Similarity	NPC233071
0.7816	Intermediate Similarity	NPC14901
0.7816	Intermediate Similarity	NPC130359
0.7763	Intermediate Similarity	NPC474823
0.775	Intermediate Similarity	NPC188860
0.7738	Intermediate Similarity	NPC229799
0.7738	Intermediate Similarity	NPC286770
0.7738	Intermediate Similarity	NPC284472
0.7722	Intermediate Similarity	NPC474321
0.7683	Intermediate Similarity	NPC1180
0.7671	Intermediate Similarity	NPC26810
0.7662	Intermediate Similarity	NPC475004
0.7662	Intermediate Similarity	NPC470436
0.7662	Intermediate Similarity	NPC236208
0.7632	Intermediate Similarity	NPC122627
0.7625	Intermediate Similarity	NPC285840
0.7625	Intermediate Similarity	NPC327041
0.7619	Intermediate Similarity	NPC11383
0.7619	Intermediate Similarity	NPC474959
0.7619	Intermediate Similarity	NPC475046
0.7619	Intermediate Similarity	NPC310450
0.7595	Intermediate Similarity	NPC327383
0.7595	Intermediate Similarity	NPC185186
0.7595	Intermediate Similarity	NPC470435
0.7564	Intermediate Similarity	NPC42526
0.7561	Intermediate Similarity	NPC473471
0.7534	Intermediate Similarity	NPC327112
0.7534	Intermediate Similarity	NPC328311
0.7531	Intermediate Similarity	NPC190400
0.7531	Intermediate Similarity	NPC49392
0.7529	Intermediate Similarity	NPC161045
0.7527	Intermediate Similarity	NPC161855
0.75	Intermediate Similarity	NPC248125
0.75	Intermediate Similarity	NPC8538
0.75	Intermediate Similarity	NPC227396
0.75	Intermediate Similarity	NPC315731
0.75	Intermediate Similarity	NPC470137
0.75	Intermediate Similarity	NPC184208
0.75	Intermediate Similarity	NPC473291
0.7471	Intermediate Similarity	NPC279267
0.7471	Intermediate Similarity	NPC308412
0.7471	Intermediate Similarity	NPC103523
0.7471	Intermediate Similarity	NPC210218
0.7471	Intermediate Similarity	NPC204686
0.7471	Intermediate Similarity	NPC473687
0.7471	Intermediate Similarity	NPC69082
0.7471	Intermediate Similarity	NPC134865
0.7471	Intermediate Similarity	NPC134885
0.7471	Intermediate Similarity	NPC134807
0.7471	Intermediate Similarity	NPC469483
0.7471	Intermediate Similarity	NPC261721
0.7471	Intermediate Similarity	NPC219498
0.747	Intermediate Similarity	NPC180725
0.7468	Intermediate Similarity	NPC316185
0.7439	Intermediate Similarity	NPC176329
0.7439	Intermediate Similarity	NPC474026
0.7439	Intermediate Similarity	NPC49302
0.7439	Intermediate Similarity	NPC125365
0.7439	Intermediate Similarity	NPC474818
0.7439	Intermediate Similarity	NPC51809
0.7407	Intermediate Similarity	NPC478193
0.7407	Intermediate Similarity	NPC469414
0.7407	Intermediate Similarity	NPC473948
0.7407	Intermediate Similarity	NPC161038
0.7407	Intermediate Similarity	NPC478196
0.7407	Intermediate Similarity	NPC478192
0.7407	Intermediate Similarity	NPC478191
0.7407	Intermediate Similarity	NPC329826
0.7407	Intermediate Similarity	NPC478195
0.7407	Intermediate Similarity	NPC478194
0.7403	Intermediate Similarity	NPC478100
0.7403	Intermediate Similarity	NPC478097
0.7397	Intermediate Similarity	NPC322002
0.7397	Intermediate Similarity	NPC329249
0.7386	Intermediate Similarity	NPC178215
0.7381	Intermediate Similarity	NPC470147
0.7381	Intermediate Similarity	NPC133226
0.7375	Intermediate Similarity	NPC287878
0.7368	Intermediate Similarity	NPC326268
0.7368	Intermediate Similarity	NPC476655
0.7368	Intermediate Similarity	NPC255863
0.7368	Intermediate Similarity	NPC19769
0.7368	Intermediate Similarity	NPC136164
0.7368	Intermediate Similarity	NPC476654
0.7368	Intermediate Similarity	NPC318420
0.7368	Intermediate Similarity	NPC476657
0.7368	Intermediate Similarity	NPC245947
0.7356	Intermediate Similarity	NPC473669
0.7356	Intermediate Similarity	NPC283085
0.7356	Intermediate Similarity	NPC103284
0.7356	Intermediate Similarity	NPC182383
0.7356	Intermediate Similarity	NPC1083
0.7356	Intermediate Similarity	NPC11804
0.7356	Intermediate Similarity	NPC110710
0.7356	Intermediate Similarity	NPC66346
0.7356	Intermediate Similarity	NPC231009
0.7356	Intermediate Similarity	NPC132496
0.7356	Intermediate Similarity	NPC261380
0.7356	Intermediate Similarity	NPC473478
0.7356	Intermediate Similarity	NPC82795
0.7356	Intermediate Similarity	NPC473651
0.7356	Intermediate Similarity	NPC470755
0.7356	Intermediate Similarity	NPC286338
0.7356	Intermediate Similarity	NPC223871
0.7356	Intermediate Similarity	NPC107986
0.7349	Intermediate Similarity	NPC248775
0.7349	Intermediate Similarity	NPC279214
0.7349	Intermediate Similarity	NPC221095
0.7333	Intermediate Similarity	NPC473455
0.7333	Intermediate Similarity	NPC475879
0.7333	Intermediate Similarity	NPC474774
0.7326	Intermediate Similarity	NPC116543
0.7317	Intermediate Similarity	NPC301207
0.7317	Intermediate Similarity	NPC127118
0.7317	Intermediate Similarity	NPC209113
0.7308	Intermediate Similarity	NPC475760
0.7308	Intermediate Similarity	NPC63873
0.7303	Intermediate Similarity	NPC20339
0.7303	Intermediate Similarity	NPC48338
0.7303	Intermediate Similarity	NPC21208
0.7303	Intermediate Similarity	NPC475819
0.7303	Intermediate Similarity	NPC233551
0.7303	Intermediate Similarity	NPC476805
0.7303	Intermediate Similarity	NPC280621
0.7303	Intermediate Similarity	NPC40376
0.7294	Intermediate Similarity	NPC112868
0.7294	Intermediate Similarity	NPC474980
0.7294	Intermediate Similarity	NPC297440
0.7294	Intermediate Similarity	NPC150502
0.7284	Intermediate Similarity	NPC114727
0.7284	Intermediate Similarity	NPC107654
0.7284	Intermediate Similarity	NPC476590
0.7284	Intermediate Similarity	NPC315843
0.7273	Intermediate Similarity	NPC62118
0.7273	Intermediate Similarity	NPC107717
0.7273	Intermediate Similarity	NPC476659
0.7273	Intermediate Similarity	NPC477015
0.7273	Intermediate Similarity	NPC476656
0.7273	Intermediate Similarity	NPC114694
0.7273	Intermediate Similarity	NPC47937
0.7273	Intermediate Similarity	NPC478101
0.7273	Intermediate Similarity	NPC240695
0.7273	Intermediate Similarity	NPC231096
0.7273	Intermediate Similarity	NPC83965
0.7273	Intermediate Similarity	NPC232555
0.7273	Intermediate Similarity	NPC208473
0.7273	Intermediate Similarity	NPC112685
0.7273	Intermediate Similarity	NPC171174
0.7273	Intermediate Similarity	NPC142117
0.7273	Intermediate Similarity	NPC475581
0.7262	Intermediate Similarity	NPC470148
0.7262	Intermediate Similarity	NPC470149
0.7241	Intermediate Similarity	NPC158756
0.7241	Intermediate Similarity	NPC473308
0.7241	Intermediate Similarity	NPC474251
0.7229	Intermediate Similarity	NPC475711
0.7229	Intermediate Similarity	NPC275530
0.7222	Intermediate Similarity	NPC473504
0.7222	Intermediate Similarity	NPC40066
0.7222	Intermediate Similarity	NPC93794
0.7222	Intermediate Similarity	NPC87306
0.7222	Intermediate Similarity	NPC42598
0.7222	Intermediate Similarity	NPC477011
0.7222	Intermediate Similarity	NPC280612
0.7222	Intermediate Similarity	NPC139418
0.7222	Intermediate Similarity	NPC318963
0.7222	Intermediate Similarity	NPC91067
0.7222	Intermediate Similarity	NPC81778
0.7222	Intermediate Similarity	NPC20621
0.7209	Intermediate Similarity	NPC251026
0.7209	Intermediate Similarity	NPC85772
0.7209	Intermediate Similarity	NPC26624
0.72	Intermediate Similarity	NPC321838
0.72	Intermediate Similarity	NPC320305
0.72	Intermediate Similarity	NPC328776
0.72	Intermediate Similarity	NPC40082
0.72	Intermediate Similarity	NPC201939
0.7191	Intermediate Similarity	NPC473248
0.7191	Intermediate Similarity	NPC72513
0.7179	Intermediate Similarity	NPC203335
0.7179	Intermediate Similarity	NPC99619
0.7179	Intermediate Similarity	NPC49863
0.7179	Intermediate Similarity	NPC26500

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 NPC182292 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	2207
0.2-0.3	3863
0.3-0.4	2112
0.4-0.5	643
0.5-0.6	122
0.6-0.7	38
0.7-0.8	3
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
0.7534	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5785	Approved
0.7209	Intermediate Similarity	NPD5209	Approved
0.7179	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD5363	Approved
0.7158	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7838	Discovery
0.6977	Remote Similarity	NPD4252	Approved
0.6889	Remote Similarity	NPD5786	Approved
0.6882	Remote Similarity	NPD7983	Approved
0.6842	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4756	Discovery
0.6818	Remote Similarity	NPD4269	Approved
0.6818	Remote Similarity	NPD4270	Approved
0.6782	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD46	Approved
0.6774	Remote Similarity	NPD6698	Approved
0.6705	Remote Similarity	NPD5369	Approved
0.6582	Remote Similarity	NPD3197	Phase 1
0.6552	Remote Similarity	NPD4271	Approved
0.6552	Remote Similarity	NPD4268	Approved
0.6489	Remote Similarity	NPD5370	Suspended
0.6458	Remote Similarity	NPD5778	Approved
0.6458	Remote Similarity	NPD5779	Approved
0.6429	Remote Similarity	NPD7839	Suspended
0.6413	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4819	Approved
0.6404	Remote Similarity	NPD4820	Approved
0.6404	Remote Similarity	NPD4821	Approved
0.6404	Remote Similarity	NPD4822	Approved
0.6374	Remote Similarity	NPD7154	Phase 3
0.6364	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD7637	Suspended
0.6354	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6371	Approved
0.6316	Remote Similarity	NPD6101	Approved
0.6316	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4225	Approved
0.6296	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD4250	Approved
0.6277	Remote Similarity	NPD4251	Approved
0.6267	Remote Similarity	NPD3195	Phase 2
0.6267	Remote Similarity	NPD3194	Approved
0.6267	Remote Similarity	NPD3196	Approved
0.6267	Remote Similarity	NPD4266	Approved
0.6264	Remote Similarity	NPD6435	Approved
0.6207	Remote Similarity	NPD8039	Approved
0.6196	Remote Similarity	NPD5362	Discontinued
0.6186	Remote Similarity	NPD6411	Approved
0.617	Remote Similarity	NPD4249	Approved
0.6154	Remote Similarity	NPD6109	Phase 1
0.6133	Remote Similarity	NPD3172	Approved
0.6129	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5343	Approved
0.6081	Remote Similarity	NPD6927	Phase 3
0.6058	Remote Similarity	NPD6647	Phase 2
0.6044	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD5368	Approved
0.6027	Remote Similarity	NPD3173	Approved
0.6022	Remote Similarity	NPD5331	Approved
0.6022	Remote Similarity	NPD5332	Approved
0.5982	Remote Similarity	NPD7115	Discovery
0.5978	Remote Similarity	NPD4790	Discontinued
0.5948	Remote Similarity	NPD7829	Approved
0.5948	Remote Similarity	NPD7830	Approved
0.5922	Remote Similarity	NPD6648	Approved
0.5895	Remote Similarity	NPD1694	Approved
0.5867	Remote Similarity	NPD28	Approved
0.5867	Remote Similarity	NPD29	Approved
0.5865	Remote Similarity	NPD5344	Discontinued
0.5854	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD7500	Approved
0.5833	Remote Similarity	NPD39	Approved
0.5833	Remote Similarity	NPD3704	Approved
0.5833	Remote Similarity	NPD4222	Approved
0.5833	Remote Similarity	NPD6686	Approved
0.5833	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD7638	Approved
0.5818	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD7642	Approved
0.58	Remote Similarity	NPD6399	Phase 3
0.5783	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD8517	Approved
0.5776	Remote Similarity	NPD8444	Approved
0.5776	Remote Similarity	NPD8515	Approved
0.5776	Remote Similarity	NPD8513	Phase 3
0.5776	Remote Similarity	NPD8516	Approved
0.5769	Remote Similarity	NPD7640	Approved
0.5769	Remote Similarity	NPD7639	Approved
0.5745	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5282	Discontinued
0.5728	Remote Similarity	NPD7902	Approved
0.5694	Remote Similarity	NPD6096	Approved
0.5694	Remote Similarity	NPD6097	Approved
0.5684	Remote Similarity	NPD6110	Phase 1
0.5676	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6650	Approved
0.5676	Remote Similarity	NPD6649	Approved
0.5652	Remote Similarity	NPD7641	Discontinued
0.5652	Remote Similarity	NPD3732	Approved
0.5636	Remote Similarity	NPD6413	Approved
0.5631	Remote Similarity	NPD4228	Discovery
0.5616	Remote Similarity	NPD3174	Discontinued
0.56	Remote Similarity	NPD4220	Pre-registration

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