NPASS Compound

Structure

NPC284006 OpenBabel07101719132D 36 36 0 0 1 0 0 0 0 0999 V2000 -1.3486 0.6651 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 -3.0391 -2.3320 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 2.8320 -6.8369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5391 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5391 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0391 -5.2638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9659 -7.3369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5391 -6.1298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0391 -2.3320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8320 -0.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8320 -0.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5391 -6.1298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -7.5958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0391 -5.2638 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 1.9659 -0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4983 -2.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8895 -3.7656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 -7.3369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 -0.2588 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8320 -6.8369 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -7.5958 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2979 -4.2979 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4897 -3.1027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8981 -3.6350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4407 -7.6303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1305 -8.5872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8724 -4.0266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0985 -2.3094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1305 0.9914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5154 -2.7112 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 5.2893 -4.4284 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 2 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 1 0 0 0 22 35 1 0 0 0 0 23 29 1 1 0 0 0 24 30 1 6 0 0 0 25 36 1 6 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:	1.186
LogD:	0.272
LogS:	-3.829
# Rotatable Bonds:	5
TPSA:	130.36
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.49
Synthetic Accessibility Score:	5.124
Fsp3:	0.464
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:	-5.242
MDCK Permeability:	3.8826481613796204e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.946
Human Intestinal Absorption (HIA):	0.061
20% Bioavailability (F20%):	0.762
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.097
Plasma Protein Binding (PPB):	91.02699279785156%
Volume Distribution (VD):	0.408
Pgp-substrate:	5.115996837615967%

ADMET: Metabolism

CYP1A2-inhibitor:	0.252
CYP1A2-substrate:	0.029
CYP2C19-inhibitor:	0.081
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.232
CYP2C9-substrate:	0.992
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.221
CYP3A4-inhibitor:	0.601
CYP3A4-substrate:	0.063

ADMET: Excretion

Clearance (CL):	1.252
Half-life (T1/2):	0.903

ADMET: Toxicity

hERG Blockers:	0.245
Human Hepatotoxicity (H-HT):	0.967
Drug-inuced Liver Injury (DILI):	0.408
AMES Toxicity:	0.801
Rat Oral Acute Toxicity:	0.179
Maximum Recommended Daily Dose:	0.993
Skin Sensitization:	0.962
Carcinogencity:	0.372
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.857

Download Data

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

Natural Product: NPC284006

Natural Product ID:	NPC284006
*Common Name:**	7-O-Succinyl Macrolactin A
IUPAC Name:	4-[[(3Z,5E,8S,9E,11Z,14S,16R,17E,19E,24R)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl]oxy]-4-oxobutanoic acid
Synonyms:
Standard InCHIKey:	QPJULYYJHQTWML-GIDLKBJSSA-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/h2,4-6,8-12,14,16,18,22-25,29-30H,3,7,13,15,17,19-21H2,1H3,(H,31,32)/b4-2+,9-5-,11-6+,14-8+,16-10+,18-12-/t22-,23+,24+,25-/m1/s1
SMILES:	C[C@@H]1CCC/C=C/C=C/[C@@H](C[C@H](C/C=CC=C[C@H](C/C=C/C=CC(=O)O1)OC(=O)CCC(=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485779
PubChem CID:	10601542
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]
NPO32830.1	Bacillus velezensis	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22385216]

☑ 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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	10.0	mm	PMID[506321]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	24.0	mm	PMID[506321]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	IZ	=	13.0	mm	PMID[506322]

☑ 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 NPC284006 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	195
0.1-0.2	1988
0.2-0.3	7622
0.3-0.4	18999
0.4-0.5	9065
0.5-0.6	3435
0.6-0.7	1147
0.7-0.8	219
0.8-0.85	17
0.85-0.9	7
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9104	High Similarity	NPC146811
0.9	High Similarity	NPC293114
0.8784	High Similarity	NPC182292
0.8592	High Similarity	NPC476037
0.8507	High Similarity	NPC26810
0.8472	Intermediate Similarity	NPC316185
0.8378	Intermediate Similarity	NPC260396
0.8356	Intermediate Similarity	NPC329890
0.8333	Intermediate Similarity	NPC476012
0.831	Intermediate Similarity	NPC63873
0.8243	Intermediate Similarity	NPC315843
0.8194	Intermediate Similarity	NPC475982
0.8171	Intermediate Similarity	NPC470137
0.8169	Intermediate Similarity	NPC122627
0.8158	Intermediate Similarity	NPC233071
0.8143	Intermediate Similarity	NPC19769
0.8108	Intermediate Similarity	NPC329914
0.8026	Intermediate Similarity	NPC188860
0.8	Intermediate Similarity	NPC107654
0.7949	Intermediate Similarity	NPC1180
0.7941	Intermediate Similarity	NPC322002
0.7917	Intermediate Similarity	NPC478097
0.7895	Intermediate Similarity	NPC478196
0.7895	Intermediate Similarity	NPC478192
0.7895	Intermediate Similarity	NPC478195
0.7895	Intermediate Similarity	NPC478193
0.7895	Intermediate Similarity	NPC478194
0.7895	Intermediate Similarity	NPC478191
0.7887	Intermediate Similarity	NPC282760
0.7887	Intermediate Similarity	NPC96414
0.7792	Intermediate Similarity	NPC256640
0.7792	Intermediate Similarity	NPC16279
0.7792	Intermediate Similarity	NPC205615
0.7778	Intermediate Similarity	NPC276299
0.7778	Intermediate Similarity	NPC201356
0.7778	Intermediate Similarity	NPC142111
0.7778	Intermediate Similarity	NPC473315
0.7763	Intermediate Similarity	NPC114727
0.7763	Intermediate Similarity	NPC476590
0.7761	Intermediate Similarity	NPC472808
0.7761	Intermediate Similarity	NPC324224
0.775	Intermediate Similarity	NPC315731
0.7746	Intermediate Similarity	NPC148233
0.7746	Intermediate Similarity	NPC25747
0.7722	Intermediate Similarity	NPC180725
0.7683	Intermediate Similarity	NPC473308
0.7681	Intermediate Similarity	NPC322186
0.7681	Intermediate Similarity	NPC97570
0.7681	Intermediate Similarity	NPC329249
0.7681	Intermediate Similarity	NPC318306
0.7671	Intermediate Similarity	NPC478100
0.7662	Intermediate Similarity	NPC327041
0.7662	Intermediate Similarity	NPC161038
0.7662	Intermediate Similarity	NPC285840
0.7654	Intermediate Similarity	NPC251026
0.7654	Intermediate Similarity	NPC313677
0.7639	Intermediate Similarity	NPC478099
0.7639	Intermediate Similarity	NPC478098
0.7632	Intermediate Similarity	NPC327383
0.7632	Intermediate Similarity	NPC185186
0.7625	Intermediate Similarity	NPC133226
0.7625	Intermediate Similarity	NPC470147
0.7606	Intermediate Similarity	NPC473737
0.76	Intermediate Similarity	NPC202011
0.7595	Intermediate Similarity	NPC248775
0.7595	Intermediate Similarity	NPC473471
0.7595	Intermediate Similarity	NPC318481
0.7571	Intermediate Similarity	NPC327112
0.7568	Intermediate Similarity	NPC474823
0.7568	Intermediate Similarity	NPC238223
0.7564	Intermediate Similarity	NPC68819
0.7561	Intermediate Similarity	NPC229799
0.7561	Intermediate Similarity	NPC116543
0.7561	Intermediate Similarity	NPC284472
0.7561	Intermediate Similarity	NPC286770
0.7561	Intermediate Similarity	NPC315559
0.7536	Intermediate Similarity	NPC223679
0.7536	Intermediate Similarity	NPC254095
0.7534	Intermediate Similarity	NPC37382
0.7534	Intermediate Similarity	NPC478101
0.7534	Intermediate Similarity	NPC124586
0.7531	Intermediate Similarity	NPC184208
0.7531	Intermediate Similarity	NPC8538
0.75	Intermediate Similarity	NPC470148
0.75	Intermediate Similarity	NPC208473
0.75	Intermediate Similarity	NPC470149
0.7468	Intermediate Similarity	NPC125365
0.7468	Intermediate Similarity	NPC474818
0.7468	Intermediate Similarity	NPC176329
0.7468	Intermediate Similarity	NPC51809
0.7468	Intermediate Similarity	NPC49302
0.7468	Intermediate Similarity	NPC474026
0.7468	Intermediate Similarity	NPC275530
0.7467	Intermediate Similarity	NPC475004
0.7467	Intermediate Similarity	NPC143396
0.7467	Intermediate Similarity	NPC470436
0.7439	Intermediate Similarity	NPC11383
0.7439	Intermediate Similarity	NPC310450
0.7439	Intermediate Similarity	NPC474959
0.7439	Intermediate Similarity	NPC475046
0.7432	Intermediate Similarity	NPC49863
0.7432	Intermediate Similarity	NPC132286
0.7429	Intermediate Similarity	NPC222852
0.7403	Intermediate Similarity	NPC470435
0.7397	Intermediate Similarity	NPC470123
0.7397	Intermediate Similarity	NPC476654
0.7397	Intermediate Similarity	NPC476655
0.7397	Intermediate Similarity	NPC476657
0.7391	Intermediate Similarity	NPC249850
0.7391	Intermediate Similarity	NPC135863
0.7391	Intermediate Similarity	NPC293437
0.7391	Intermediate Similarity	NPC294938
0.7391	Intermediate Similarity	NPC129150
0.7375	Intermediate Similarity	NPC279214
0.7375	Intermediate Similarity	NPC221095
0.7368	Intermediate Similarity	NPC329904
0.7368	Intermediate Similarity	NPC473361
0.7368	Intermediate Similarity	NPC59558
0.7361	Intermediate Similarity	NPC474774
0.7361	Intermediate Similarity	NPC68110
0.7356	Intermediate Similarity	NPC473311
0.7349	Intermediate Similarity	NPC169575
0.7349	Intermediate Similarity	NPC40746
0.7349	Intermediate Similarity	NPC16488
0.7342	Intermediate Similarity	NPC301207
0.7342	Intermediate Similarity	NPC470705
0.7342	Intermediate Similarity	NPC127118
0.7342	Intermediate Similarity	NPC209113
0.7333	Intermediate Similarity	NPC475760
0.7324	Intermediate Similarity	NPC328311
0.7324	Intermediate Similarity	NPC321919
0.7324	Intermediate Similarity	NPC26223
0.7324	Intermediate Similarity	NPC81896
0.7308	Intermediate Similarity	NPC474321
0.7297	Intermediate Similarity	NPC476656
0.7297	Intermediate Similarity	NPC476659
0.7297	Intermediate Similarity	NPC328653
0.7297	Intermediate Similarity	NPC248125
0.7294	Intermediate Similarity	NPC315395
0.7294	Intermediate Similarity	NPC316426
0.7262	Intermediate Similarity	NPC161670
0.726	Intermediate Similarity	NPC470808
0.726	Intermediate Similarity	NPC476658
0.726	Intermediate Similarity	NPC308457
0.7237	Intermediate Similarity	NPC476591
0.7237	Intermediate Similarity	NPC236208
0.7237	Intermediate Similarity	NPC88877
0.7237	Intermediate Similarity	NPC151481
0.7229	Intermediate Similarity	NPC26624
0.7222	Intermediate Similarity	NPC113293
0.7222	Intermediate Similarity	NPC55376
0.7215	Intermediate Similarity	NPC473948
0.7215	Intermediate Similarity	NPC473582
0.7209	Intermediate Similarity	NPC475186
0.7209	Intermediate Similarity	NPC178215
0.7209	Intermediate Similarity	NPC118077
0.72	Intermediate Similarity	NPC203335
0.72	Intermediate Similarity	NPC25298
0.7183	Intermediate Similarity	NPC82465
0.7176	Intermediate Similarity	NPC470755
0.7174	Intermediate Similarity	NPC203627
0.7162	Intermediate Similarity	NPC245947
0.7162	Intermediate Similarity	NPC471556
0.7162	Intermediate Similarity	NPC255863
0.7162	Intermediate Similarity	NPC323477
0.7162	Intermediate Similarity	NPC471566
0.7162	Intermediate Similarity	NPC471565
0.7162	Intermediate Similarity	NPC317881
0.7162	Intermediate Similarity	NPC323045
0.7162	Intermediate Similarity	NPC136164
0.7162	Intermediate Similarity	NPC273600
0.716	Intermediate Similarity	NPC477314
0.716	Intermediate Similarity	NPC108816
0.716	Intermediate Similarity	NPC279532
0.716	Intermediate Similarity	NPC93763
0.7143	Intermediate Similarity	NPC323436
0.7143	Intermediate Similarity	NPC44261
0.7143	Intermediate Similarity	NPC44542
0.7143	Intermediate Similarity	NPC323498
0.7143	Intermediate Similarity	NPC131669
0.7143	Intermediate Similarity	NPC211752
0.7143	Intermediate Similarity	NPC323597
0.7143	Intermediate Similarity	NPC473390
0.7143	Intermediate Similarity	NPC472445
0.7126	Intermediate Similarity	NPC48338
0.7126	Intermediate Similarity	NPC280621
0.7126	Intermediate Similarity	NPC40376
0.7126	Intermediate Similarity	NPC233551
0.7126	Intermediate Similarity	NPC21208
0.7126	Intermediate Similarity	NPC476805
0.7126	Intermediate Similarity	NPC20339
0.7126	Intermediate Similarity	NPC475819
0.7125	Intermediate Similarity	NPC203277
0.7123	Intermediate Similarity	NPC179087
0.7123	Intermediate Similarity	NPC210303
0.7123	Intermediate Similarity	NPC2328
0.7123	Intermediate Similarity	NPC44343
0.7108	Intermediate Similarity	NPC297440
0.7108	Intermediate Similarity	NPC112868
0.7108	Intermediate Similarity	NPC150502

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 NPC284006 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	2473
0.2-0.3	4043
0.3-0.4	1952
0.4-0.5	399
0.5-0.6	98
0.6-0.7	23
0.7-0.8	2
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
0.7571	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7838	Discovery
0.6786	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6698	Approved
0.6593	Remote Similarity	NPD46	Approved
0.6593	Remote Similarity	NPD5785	Approved
0.6575	Remote Similarity	NPD6109	Phase 1
0.6548	Remote Similarity	NPD4268	Approved
0.6548	Remote Similarity	NPD4271	Approved
0.6522	Remote Similarity	NPD7983	Approved
0.6522	Remote Similarity	NPD6927	Phase 3
0.6477	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4756	Discovery
0.6404	Remote Similarity	NPD5363	Approved
0.6395	Remote Similarity	NPD4819	Approved
0.6395	Remote Similarity	NPD4820	Approved
0.6395	Remote Similarity	NPD4821	Approved
0.6395	Remote Similarity	NPD4822	Approved
0.6364	Remote Similarity	NPD7154	Phase 3
0.6351	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD5343	Approved
0.6269	Remote Similarity	NPD39	Approved
0.6264	Remote Similarity	NPD4250	Approved
0.6264	Remote Similarity	NPD4251	Approved
0.625	Remote Similarity	NPD5209	Approved
0.6232	Remote Similarity	NPD4220	Pre-registration
0.6222	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4252	Approved
0.617	Remote Similarity	NPD7637	Suspended
0.6154	Remote Similarity	NPD3197	Phase 1
0.6154	Remote Similarity	NPD5786	Approved
0.6154	Remote Similarity	NPD4249	Approved
0.6146	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD9119	Approved
0.6133	Remote Similarity	NPD69	Approved
0.6122	Remote Similarity	NPD4225	Approved
0.6119	Remote Similarity	NPD6096	Approved
0.6119	Remote Similarity	NPD6097	Approved
0.6105	Remote Similarity	NPD5779	Approved
0.6105	Remote Similarity	NPD5778	Approved
0.6082	Remote Similarity	NPD7839	Suspended
0.6076	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD4269	Approved
0.6067	Remote Similarity	NPD4270	Approved
0.6061	Remote Similarity	NPD6648	Approved
0.6029	Remote Similarity	NPD4222	Approved
0.6	Remote Similarity	NPD5344	Discontinued
0.6	Remote Similarity	NPD3173	Approved
0.6	Remote Similarity	NPD5362	Discontinued
0.6	Remote Similarity	NPD9118	Approved
0.5977	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.597	Remote Similarity	NPD5326	Phase 3
0.5889	Remote Similarity	NPD6435	Approved
0.5865	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6371	Approved
0.5824	Remote Similarity	NPD5331	Approved
0.5824	Remote Similarity	NPD5332	Approved
0.5814	Remote Similarity	NPD8039	Approved
0.5811	Remote Similarity	NPD4266	Approved
0.5811	Remote Similarity	NPD3195	Phase 2
0.5811	Remote Similarity	NPD3196	Approved
0.5811	Remote Similarity	NPD3194	Approved
0.5797	Remote Similarity	NPD4265	Approved
0.5789	Remote Similarity	NPD6101	Approved
0.5789	Remote Similarity	NPD5370	Suspended
0.5789	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD5369	Approved
0.5778	Remote Similarity	NPD4790	Discontinued
0.575	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD6647	Phase 2
0.5676	Remote Similarity	NPD3172	Approved
0.567	Remote Similarity	NPD6411	Approved
0.567	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD5368	Approved
0.566	Remote Similarity	NPD6686	Approved
0.5652	Remote Similarity	NPD6110	Phase 1
0.5648	Remote Similarity	NPD8413	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