NPASS Compound

Structure

NPC189629 OpenBabel07101718192D 29 30 0 0 1 0 0 0 0 0999 V2000 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 5.3660 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2321 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6340 1.3660 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 3.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8660 -2.9641 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 0.8660 -1.5000 0.0000 C 0 0 2 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 4.3660 -0.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3660 -2.0981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3660 -0.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8660 -1.2321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3660 1.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3660 -2.0981 0.0000 C 0 0 0 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 2.8660 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8660 -2.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8660 -1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8660 2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8660 -1.2321 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 10 2 0 0 0 0 4 19 1 0 0 0 0 5 19 1 0 0 0 0 6 27 1 0 0 0 0 7 10 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 11 2 1 1 0 0 0 11 12 1 0 0 0 0 12 3 1 1 0 0 0 12 29 1 0 0 0 0 13 8 1 6 0 0 0 13 15 1 0 0 0 0 13 28 1 0 0 0 0 14 9 1 1 0 0 0 14 19 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 23 1 6 0 0 0 16 19 1 0 0 0 0 16 24 1 1 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 17 25 1 6 0 0 0 18 21 2 3 0 0 0 18 26 1 0 0 0 0 20 27 1 6 0 0 0 20 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	417.24
Volume:	413.409
LogP:	1.153
LogD:	1.164
LogS:	-1.621
# Rotatable Bonds:	7
TPSA:	137.71
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.269
Synthetic Accessibility Score:	5.3
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.334
MDCK Permeability:	8.152595546562225e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.944
Human Intestinal Absorption (HIA):	0.179
20% Bioavailability (F20%):	0.142
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.126
Plasma Protein Binding (PPB):	41.13440704345703%
Volume Distribution (VD):	0.435
Pgp-substrate:	66.56645202636719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.07
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.757
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.147
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.348

ADMET: Excretion

Clearance (CL):	3.438
Half-life (T1/2):	0.87

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.471
Drug-inuced Liver Injury (DILI):	0.469
AMES Toxicity:	0.864
Rat Oral Acute Toxicity:	0.672
Maximum Recommended Daily Dose:	0.603
Skin Sensitization:	0.195
Carcinogencity:	0.13
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.465

Download Data

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

Natural Product: NPC189629

Natural Product ID:	NPC189629
*Common Name:**	Mycalamide C
IUPAC Name:	(2S)-N-[[(2R,3R,4S,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5,5-dimethyloxan-2-yl]methyl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]acetamide
Synonyms:	Mycalamide C
Standard InCHIKey:	DCZMMILMODFEMS-AUYDAGNDSA-N
Standard InCHI:	InChI=1S/C20H35NO8/c1-10-7-20(27-6,29-12(3)11(10)2)17(25)18(26)21-8-13-15(23)16(24)19(4,5)14(9-22)28-13/h11-17,22-25H,1,7-9H2,2-6H3,(H,21,26)/t11-,12-,13-,14-,15+,16-,17-,20-/m1/s1
SMILES:	OC[C@H]1O[C@H](CN=C([C@H]([C@@]2(OC)CC(=C)[C@H]([C@H](O2)C)C)O)O)[C@@H]([C@H](C1(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509856
PubChem CID:	10002037
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002204] C-glycosyl compounds

*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
NPO33503	stylinos n. species	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10843596]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.095	ug.mL-1	PMID[511815]

☑ 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 NPC189629 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	86
0.1-0.2	904
0.2-0.3	8422
0.3-0.4	17483
0.4-0.5	10474
0.5-0.6	4964
0.6-0.7	327
0.7-0.8	28
0.8-0.85	3
0.85-0.9	0
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9674	High Similarity	NPC225978
0.9674	High Similarity	NPC206711
0.9674	High Similarity	NPC255175
0.9674	High Similarity	NPC271207
0.8119	Intermediate Similarity	NPC477198
0.798	Intermediate Similarity	NPC475503
0.7812	Intermediate Similarity	NPC470284
0.7766	Intermediate Similarity	NPC476523
0.7723	Intermediate Similarity	NPC475646
0.7576	Intermediate Similarity	NPC61894
0.7576	Intermediate Similarity	NPC475603
0.7426	Intermediate Similarity	NPC470283
0.7328	Intermediate Similarity	NPC469943
0.7255	Intermediate Similarity	NPC3568
0.7255	Intermediate Similarity	NPC192066
0.7255	Intermediate Similarity	NPC23454
0.7255	Intermediate Similarity	NPC35269
0.7255	Intermediate Similarity	NPC256570
0.7255	Intermediate Similarity	NPC262312
0.7255	Intermediate Similarity	NPC17290
0.7255	Intermediate Similarity	NPC70323
0.7222	Intermediate Similarity	NPC475918
0.7207	Intermediate Similarity	NPC29501
0.7115	Intermediate Similarity	NPC8098
0.7115	Intermediate Similarity	NPC45313
0.7115	Intermediate Similarity	NPC197294
0.7115	Intermediate Similarity	NPC183449
0.7091	Intermediate Similarity	NPC475150
0.7059	Intermediate Similarity	NPC309898
0.7059	Intermediate Similarity	NPC473581
0.7059	Intermediate Similarity	NPC182632
0.7059	Intermediate Similarity	NPC15851
0.7059	Intermediate Similarity	NPC473950
0.7059	Intermediate Similarity	NPC473604
0.7059	Intermediate Similarity	NPC263545
0.7059	Intermediate Similarity	NPC475125
0.7059	Intermediate Similarity	NPC282705
0.7059	Intermediate Similarity	NPC111567
0.7059	Intermediate Similarity	NPC186840
0.7027	Intermediate Similarity	NPC473578
0.7	Intermediate Similarity	NPC470282
0.6961	Remote Similarity	NPC209047
0.6961	Remote Similarity	NPC74672
0.6961	Remote Similarity	NPC242503
0.6961	Remote Similarity	NPC43074
0.6961	Remote Similarity	NPC139782
0.6935	Remote Similarity	NPC119794
0.6935	Remote Similarity	NPC73829
0.6923	Remote Similarity	NPC54961
0.6923	Remote Similarity	NPC282088
0.6923	Remote Similarity	NPC156782
0.6923	Remote Similarity	NPC158445
0.6923	Remote Similarity	NPC157353
0.6893	Remote Similarity	NPC208537
0.6893	Remote Similarity	NPC270005
0.6869	Remote Similarity	NPC477199
0.6855	Remote Similarity	NPC139585
0.6855	Remote Similarity	NPC475472
0.6842	Remote Similarity	NPC469865
0.6825	Remote Similarity	NPC235772
0.6825	Remote Similarity	NPC280941
0.6825	Remote Similarity	NPC75318
0.6772	Remote Similarity	NPC145899
0.6771	Remote Similarity	NPC316807
0.6748	Remote Similarity	NPC329919
0.6748	Remote Similarity	NPC477793
0.6746	Remote Similarity	NPC477072
0.6746	Remote Similarity	NPC76999
0.6735	Remote Similarity	NPC16090
0.6667	Remote Similarity	NPC200788
0.6667	Remote Similarity	NPC243680
0.6635	Remote Similarity	NPC477865
0.6635	Remote Similarity	NPC477866
0.6615	Remote Similarity	NPC302276
0.6615	Remote Similarity	NPC180770
0.6607	Remote Similarity	NPC201128
0.6604	Remote Similarity	NPC72817
0.6604	Remote Similarity	NPC477927
0.6574	Remote Similarity	NPC76486
0.6565	Remote Similarity	NPC82931
0.6565	Remote Similarity	NPC172365
0.6565	Remote Similarity	NPC210729
0.6541	Remote Similarity	NPC141669
0.6535	Remote Similarity	NPC166279
0.6518	Remote Similarity	NPC74035
0.6515	Remote Similarity	NPC162910
0.6504	Remote Similarity	NPC469494
0.65	Remote Similarity	NPC20072
0.6466	Remote Similarity	NPC475152
0.6466	Remote Similarity	NPC475584
0.6466	Remote Similarity	NPC475394
0.6465	Remote Similarity	NPC100697
0.6465	Remote Similarity	NPC471420
0.6455	Remote Similarity	NPC91497
0.6455	Remote Similarity	NPC64348
0.6442	Remote Similarity	NPC248312
0.6418	Remote Similarity	NPC284625
0.6418	Remote Similarity	NPC298469
0.6418	Remote Similarity	NPC475892
0.6418	Remote Similarity	NPC193579
0.6418	Remote Similarity	NPC69176
0.6415	Remote Similarity	NPC302584
0.6413	Remote Similarity	NPC195165
0.6413	Remote Similarity	NPC477758
0.6413	Remote Similarity	NPC477761
0.6413	Remote Similarity	NPC477759
0.6413	Remote Similarity	NPC477760
0.6413	Remote Similarity	NPC477754
0.6383	Remote Similarity	NPC477200
0.6374	Remote Similarity	NPC147292
0.6371	Remote Similarity	NPC296686
0.637	Remote Similarity	NPC298067
0.637	Remote Similarity	NPC214821
0.6364	Remote Similarity	NPC477928
0.6364	Remote Similarity	NPC56071
0.6364	Remote Similarity	NPC265908
0.6364	Remote Similarity	NPC70733
0.6355	Remote Similarity	NPC67398
0.6355	Remote Similarity	NPC474835
0.6355	Remote Similarity	NPC91654
0.6355	Remote Similarity	NPC474792
0.6348	Remote Similarity	NPC70235
0.6339	Remote Similarity	NPC272015
0.6337	Remote Similarity	NPC477385
0.6337	Remote Similarity	NPC477390
0.633	Remote Similarity	NPC90583
0.633	Remote Similarity	NPC472989
0.6321	Remote Similarity	NPC159876
0.632	Remote Similarity	NPC48886
0.632	Remote Similarity	NPC94881
0.632	Remote Similarity	NPC265275
0.6304	Remote Similarity	NPC477751
0.6304	Remote Similarity	NPC36463
0.6304	Remote Similarity	NPC477764
0.6304	Remote Similarity	NPC477752
0.6304	Remote Similarity	NPC477756
0.6304	Remote Similarity	NPC298005
0.6296	Remote Similarity	NPC305160
0.6289	Remote Similarity	NPC264417
0.6289	Remote Similarity	NPC217095
0.6283	Remote Similarity	NPC55336
0.6281	Remote Similarity	NPC471118
0.6281	Remote Similarity	NPC471121
0.6277	Remote Similarity	NPC244380
0.6277	Remote Similarity	NPC61717
0.6273	Remote Similarity	NPC473890
0.6273	Remote Similarity	NPC240372
0.6273	Remote Similarity	NPC243728
0.6273	Remote Similarity	NPC278506
0.6271	Remote Similarity	NPC279383
0.6271	Remote Similarity	NPC314306
0.6263	Remote Similarity	NPC150557
0.6261	Remote Similarity	NPC317534
0.6261	Remote Similarity	NPC315426
0.626	Remote Similarity	NPC469515
0.626	Remote Similarity	NPC297058
0.625	Remote Similarity	NPC470836
0.625	Remote Similarity	NPC470168
0.625	Remote Similarity	NPC172197
0.625	Remote Similarity	NPC117714
0.625	Remote Similarity	NPC274293
0.625	Remote Similarity	NPC263756
0.624	Remote Similarity	NPC313333
0.624	Remote Similarity	NPC313342
0.624	Remote Similarity	NPC314512
0.624	Remote Similarity	NPC314451
0.6239	Remote Similarity	NPC108141
0.6239	Remote Similarity	NPC473348
0.6228	Remote Similarity	NPC221562
0.6228	Remote Similarity	NPC470885
0.6228	Remote Similarity	NPC109792
0.6228	Remote Similarity	NPC475521
0.6228	Remote Similarity	NPC470768
0.6228	Remote Similarity	NPC54521
0.6228	Remote Similarity	NPC57065
0.6228	Remote Similarity	NPC187400
0.6226	Remote Similarity	NPC159369
0.6226	Remote Similarity	NPC473058
0.6226	Remote Similarity	NPC39290
0.6224	Remote Similarity	NPC293223
0.6216	Remote Similarity	NPC158088
0.6216	Remote Similarity	NPC474952
0.6211	Remote Similarity	NPC471879
0.6204	Remote Similarity	NPC296620
0.6202	Remote Similarity	NPC25455
0.6202	Remote Similarity	NPC15249
0.6198	Remote Similarity	NPC471120
0.6198	Remote Similarity	NPC471117
0.6195	Remote Similarity	NPC256133
0.6195	Remote Similarity	NPC213674
0.6195	Remote Similarity	NPC136816
0.6195	Remote Similarity	NPC76497
0.6195	Remote Similarity	NPC288694
0.6195	Remote Similarity	NPC312553
0.6195	Remote Similarity	NPC30289
0.6195	Remote Similarity	NPC159036
0.6186	Remote Similarity	NPC138273
0.6186	Remote Similarity	NPC308489
0.6182	Remote Similarity	NPC207617
0.6174	Remote Similarity	NPC473476

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 NPC189629 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	81
0.1-0.2	702
0.2-0.3	4129
0.3-0.4	3176
0.4-0.5	823
0.5-0.6	202
0.6-0.7	37
0.7-0.8	0
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
0.7091	Intermediate Similarity	NPD8174	Phase 2
0.6961	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6421	Discontinued
0.6607	Remote Similarity	NPD5357	Phase 1
0.6333	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3187	Discontinued
0.6316	Remote Similarity	NPD6640	Phase 3
0.6293	Remote Similarity	NPD8306	Approved
0.6293	Remote Similarity	NPD8305	Approved
0.6271	Remote Similarity	NPD6429	Approved
0.6271	Remote Similarity	NPD6430	Approved
0.626	Remote Similarity	NPD8267	Approved
0.626	Remote Similarity	NPD8269	Approved
0.626	Remote Similarity	NPD8268	Approved
0.626	Remote Similarity	NPD8266	Approved
0.624	Remote Similarity	NPD8299	Approved
0.624	Remote Similarity	NPD8342	Approved
0.624	Remote Similarity	NPD8341	Approved
0.624	Remote Similarity	NPD8340	Approved
0.621	Remote Similarity	NPD6436	Phase 3
0.619	Remote Similarity	NPD8451	Approved
0.6182	Remote Similarity	NPD6428	Approved
0.6174	Remote Similarity	NPD5376	Approved
0.6168	Remote Similarity	NPD3168	Discontinued
0.6154	Remote Similarity	NPD8449	Approved
0.6148	Remote Similarity	NPD7641	Discontinued
0.6142	Remote Similarity	NPD8448	Approved
0.614	Remote Similarity	NPD8275	Approved
0.614	Remote Similarity	NPD8276	Approved
0.6129	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD8390	Approved
0.6124	Remote Similarity	NPD8391	Approved
0.6124	Remote Similarity	NPD8392	Approved
0.6121	Remote Similarity	NPD8307	Discontinued
0.6121	Remote Similarity	NPD8140	Approved
0.6107	Remote Similarity	NPD8450	Suspended
0.6105	Remote Similarity	NPD9445	Approved
0.6091	Remote Similarity	NPD7844	Discontinued
0.6091	Remote Similarity	NPD5381	Approved
0.6091	Remote Similarity	NPD5378	Approved
0.6091	Remote Similarity	NPD5377	Approved
0.608	Remote Similarity	NPD8080	Discontinued
0.6053	Remote Similarity	NPD8139	Approved
0.6053	Remote Similarity	NPD8083	Approved
0.6053	Remote Similarity	NPD8084	Approved
0.6053	Remote Similarity	NPD8085	Approved
0.6053	Remote Similarity	NPD8086	Approved
0.6053	Remote Similarity	NPD8138	Approved
0.6053	Remote Similarity	NPD8082	Approved
0.6038	Remote Similarity	NPD4759	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD3191	Approved
0.6036	Remote Similarity	NPD3190	Approved
0.6036	Remote Similarity	NPD3189	Approved
0.6034	Remote Similarity	NPD8393	Approved
0.6	Remote Similarity	NPD1407	Approved
0.5966	Remote Similarity	NPD8087	Discontinued
0.5948	Remote Similarity	NPD8081	Approved
0.5926	Remote Similarity	NPD3716	Discontinued
0.5909	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD7830	Approved
0.5906	Remote Similarity	NPD7829	Approved
0.5862	Remote Similarity	NPD8045	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD618	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD6686	Approved
0.5789	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD8074	Phase 3
0.5766	Remote Similarity	NPD1446	Phase 3
0.5766	Remote Similarity	NPD1447	Phase 3
0.5763	Remote Similarity	NPD4211	Phase 1
0.5758	Remote Similarity	NPD6914	Discontinued
0.575	Remote Similarity	NPD6941	Approved
0.5748	Remote Similarity	NPD8444	Approved
0.5745	Remote Similarity	NPD1831	Phase 3
0.5741	Remote Similarity	NPD7524	Approved
0.5739	Remote Similarity	NPD4838	Approved
0.5739	Remote Similarity	NPD4837	Approved
0.5739	Remote Similarity	NPD4836	Approved
0.5739	Remote Similarity	NPD4835	Approved
0.5727	Remote Similarity	NPD6698	Approved
0.5727	Remote Similarity	NPD46	Approved
0.5714	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6412	Phase 2
0.5704	Remote Similarity	NPD7625	Phase 1
0.5704	Remote Similarity	NPD8415	Approved
0.5691	Remote Similarity	NPD3731	Phase 3
0.5691	Remote Similarity	NPD8133	Approved
0.568	Remote Similarity	NPD7500	Approved
0.568	Remote Similarity	NPD7505	Discontinued
0.5669	Remote Similarity	NPD8346	Approved
0.5669	Remote Similarity	NPD8345	Approved
0.5669	Remote Similarity	NPD8347	Approved
0.5659	Remote Similarity	NPD7642	Approved
0.5656	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD2255	Approved
0.5641	Remote Similarity	NPD7140	Approved
0.5641	Remote Similarity	NPD7139	Approved
0.5641	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.56	Remote Similarity	NPD4832	Approved
0.56	Remote Similarity	NPD4831	Approved
0.56	Remote Similarity	NPD4830	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