NPASS Compound

Structure

NPC470435 OpenBabel07101719132D 23 23 0 0 1 0 0 0 0 0999 V2000 6.6858 -0.6807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5812 -1.6753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6677 -2.0820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8587 -1.4942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9451 -1.9009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1361 -1.3132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2226 -1.7199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4135 -1.1321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9271 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2361 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1180 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1180 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1180 1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9271 -0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1180 -1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4271 2.4899 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7361 -1.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4271 -2.4899 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 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 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 10 11 2 0 0 0 0 10 14 1 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 19 1 6 0 0 0 15 9 1 1 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 20 1 6 0 0 0 17 21 1 1 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.22
Volume:	350.006
LogP:	3.216
LogD:	2.17
LogS:	-4.538
# Rotatable Bonds:	8
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.362
Synthetic Accessibility Score:	4.247
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.03
MDCK Permeability:	6.389019836205989e-05
Pgp-inhibitor:	0.211
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.408
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.668
Plasma Protein Binding (PPB):	87.61075592041016%
Volume Distribution (VD):	0.886
Pgp-substrate:	2.9034619331359863%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.097
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.98
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.069
CYP3A4-inhibitor:	0.094
CYP3A4-substrate:	0.08

ADMET: Excretion

Clearance (CL):	4.878
Half-life (T1/2):	0.649

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.555
Drug-inuced Liver Injury (DILI):	0.27
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.646
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.746
Carcinogencity:	0.044
Eye Corrosion:	0.005
Eye Irritation:	0.165
Respiratory Toxicity:	0.867

Download Data

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

Natural Product: NPC470435

Natural Product ID:	NPC470435
*Common Name:**	Seimatopolide A
IUPAC Name:	(2S,4R,5R,6E,8R)-4,5,8-trihydroxy-2-nonyl-2,3,4,5,8,9-hexahydrooxecin-10-one
Synonyms:	Seimatopolide A
Standard InCHIKey:	VKFBQLMPTJTKBZ-ISHVXOLWSA-N
Standard InCHI:	InChI=1S/C18H32O5/c1-2-3-4-5-6-7-8-9-15-13-17(21)16(20)11-10-14(19)12-18(22)23-15/h10-11,14-17,19-21H,2-9,12-13H2,1H3/b11-10+/t14-,15-,16+,17+/m0/s1
SMILES:	CCCCCCCCC[C@@H]1OC(=O)C[C@@H](O)/C=C/[C@H]([C@@H](C1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2036277
PubChem CID:	57409555
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001796] Oxocins

*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
NPO33344	seimatosporium discosioides	Species	Amphisphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22424300]

☑ 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
EC50	1
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	EC50	=	1150.0	nM	PMID[458870]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	FC	=	2.0	n.a.	PMID[458870]

☑ 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 NPC470435 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	185
0.1-0.2	1931
0.2-0.3	6605
0.3-0.4	18245
0.4-0.5	9778
0.5-0.6	4411
0.6-0.7	1316
0.7-0.8	209
0.8-0.85	13
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9552	High Similarity	NPC470436
0.8696	High Similarity	NPC25298
0.8451	Intermediate Similarity	NPC130618
0.8429	Intermediate Similarity	NPC26500
0.8429	Intermediate Similarity	NPC99619
0.8235	Intermediate Similarity	NPC113293
0.8235	Intermediate Similarity	NPC321838
0.8169	Intermediate Similarity	NPC104537
0.8169	Intermediate Similarity	NPC330426
0.8169	Intermediate Similarity	NPC271921
0.8169	Intermediate Similarity	NPC22101
0.8169	Intermediate Similarity	NPC148192
0.8169	Intermediate Similarity	NPC127091
0.8133	Intermediate Similarity	NPC473582
0.8082	Intermediate Similarity	NPC42526
0.8056	Intermediate Similarity	NPC473559
0.8056	Intermediate Similarity	NPC48218
0.8056	Intermediate Similarity	NPC324981
0.8056	Intermediate Similarity	NPC141481
0.8026	Intermediate Similarity	NPC49392
0.8026	Intermediate Similarity	NPC190400
0.8	Intermediate Similarity	NPC473489
0.8	Intermediate Similarity	NPC326504
0.7917	Intermediate Similarity	NPC478097
0.7917	Intermediate Similarity	NPC475443
0.7917	Intermediate Similarity	NPC473829
0.7895	Intermediate Similarity	NPC260396
0.7887	Intermediate Similarity	NPC476657
0.7887	Intermediate Similarity	NPC476654
0.7887	Intermediate Similarity	NPC476655
0.7857	Intermediate Similarity	NPC29697
0.7838	Intermediate Similarity	NPC476660
0.7826	Intermediate Similarity	NPC81896
0.7826	Intermediate Similarity	NPC321919
0.7821	Intermediate Similarity	NPC318481
0.7821	Intermediate Similarity	NPC248775
0.7778	Intermediate Similarity	NPC476656
0.7778	Intermediate Similarity	NPC476659
0.7746	Intermediate Similarity	NPC475221
0.7746	Intermediate Similarity	NPC476658
0.7722	Intermediate Similarity	NPC470148
0.7722	Intermediate Similarity	NPC1180
0.7722	Intermediate Similarity	NPC470149
0.7722	Intermediate Similarity	NPC180725
0.7714	Intermediate Similarity	NPC325929
0.7714	Intermediate Similarity	NPC320305
0.7714	Intermediate Similarity	NPC201939
0.7714	Intermediate Similarity	NPC328776
0.7714	Intermediate Similarity	NPC271282
0.7714	Intermediate Similarity	NPC66460
0.7703	Intermediate Similarity	NPC473772
0.7681	Intermediate Similarity	NPC322186
0.7681	Intermediate Similarity	NPC318306
0.7671	Intermediate Similarity	NPC478100
0.7662	Intermediate Similarity	NPC473948
0.7647	Intermediate Similarity	NPC323436
0.7639	Intermediate Similarity	NPC478099
0.7639	Intermediate Similarity	NPC478098
0.7639	Intermediate Similarity	NPC136164
0.7639	Intermediate Similarity	NPC245947
0.7639	Intermediate Similarity	NPC255863
0.7632	Intermediate Similarity	NPC329890
0.7632	Intermediate Similarity	NPC325627
0.7625	Intermediate Similarity	NPC133226
0.7625	Intermediate Similarity	NPC470147
0.7612	Intermediate Similarity	NPC52264
0.7595	Intermediate Similarity	NPC182292
0.7595	Intermediate Similarity	NPC473471
0.7571	Intermediate Similarity	NPC243532
0.7571	Intermediate Similarity	NPC327112
0.7568	Intermediate Similarity	NPC273508
0.7568	Intermediate Similarity	NPC63873
0.7568	Intermediate Similarity	NPC209327
0.7561	Intermediate Similarity	NPC284472
0.7561	Intermediate Similarity	NPC229799
0.7561	Intermediate Similarity	NPC286770
0.7534	Intermediate Similarity	NPC284447
0.7534	Intermediate Similarity	NPC478101
0.7532	Intermediate Similarity	NPC474321
0.75	Intermediate Similarity	NPC469910
0.75	Intermediate Similarity	NPC68343
0.75	Intermediate Similarity	NPC470320
0.75	Intermediate Similarity	NPC328089
0.75	Intermediate Similarity	NPC293114
0.7468	Intermediate Similarity	NPC474818
0.7468	Intermediate Similarity	NPC176329
0.7468	Intermediate Similarity	NPC233071
0.7468	Intermediate Similarity	NPC125365
0.7468	Intermediate Similarity	NPC51809
0.7468	Intermediate Similarity	NPC49302
0.7468	Intermediate Similarity	NPC474026
0.7468	Intermediate Similarity	NPC474278
0.7465	Intermediate Similarity	NPC475984
0.7463	Intermediate Similarity	NPC137538
0.7439	Intermediate Similarity	NPC11383
0.7439	Intermediate Similarity	NPC474252
0.7439	Intermediate Similarity	NPC310450
0.7439	Intermediate Similarity	NPC474959
0.7439	Intermediate Similarity	NPC475046
0.7403	Intermediate Similarity	NPC185186
0.7403	Intermediate Similarity	NPC284006
0.7403	Intermediate Similarity	NPC327383
0.7403	Intermediate Similarity	NPC329914
0.7397	Intermediate Similarity	NPC318420
0.7397	Intermediate Similarity	NPC326268
0.7397	Intermediate Similarity	NPC19769
0.7381	Intermediate Similarity	NPC11804
0.7375	Intermediate Similarity	NPC221095
0.7375	Intermediate Similarity	NPC39547
0.7375	Intermediate Similarity	NPC260814
0.7375	Intermediate Similarity	NPC218817
0.7375	Intermediate Similarity	NPC279214
0.7375	Intermediate Similarity	NPC127526
0.7375	Intermediate Similarity	NPC323249
0.7375	Intermediate Similarity	NPC27949
0.7375	Intermediate Similarity	NPC11796
0.7368	Intermediate Similarity	NPC4299
0.7368	Intermediate Similarity	NPC476037
0.7361	Intermediate Similarity	NPC470965
0.7361	Intermediate Similarity	NPC54925
0.7356	Intermediate Similarity	NPC313670
0.7349	Intermediate Similarity	NPC161045
0.7342	Intermediate Similarity	NPC127118
0.7342	Intermediate Similarity	NPC209113
0.7342	Intermediate Similarity	NPC301207
0.7342	Intermediate Similarity	NPC188860
0.7326	Intermediate Similarity	NPC476803
0.7324	Intermediate Similarity	NPC328311
0.7297	Intermediate Similarity	NPC146811
0.7297	Intermediate Similarity	NPC83965
0.7284	Intermediate Similarity	NPC263574
0.7284	Intermediate Similarity	NPC469747
0.7284	Intermediate Similarity	NPC86971
0.7284	Intermediate Similarity	NPC475210
0.7273	Intermediate Similarity	NPC472199
0.7262	Intermediate Similarity	NPC158756
0.726	Intermediate Similarity	NPC226592
0.725	Intermediate Similarity	NPC475711
0.725	Intermediate Similarity	NPC281296
0.7237	Intermediate Similarity	NPC475982
0.7237	Intermediate Similarity	NPC101622
0.7237	Intermediate Similarity	NPC143396
0.7222	Intermediate Similarity	NPC26810
0.7215	Intermediate Similarity	NPC285840
0.7215	Intermediate Similarity	NPC327041
0.7209	Intermediate Similarity	NPC477959
0.7209	Intermediate Similarity	NPC86005
0.72	Intermediate Similarity	NPC193029
0.72	Intermediate Similarity	NPC49863
0.72	Intermediate Similarity	NPC473357
0.7195	Intermediate Similarity	NPC47653
0.7183	Intermediate Similarity	NPC329249
0.7183	Intermediate Similarity	NPC322002
0.7179	Intermediate Similarity	NPC477085
0.7179	Intermediate Similarity	NPC144419
0.7176	Intermediate Similarity	NPC77971
0.7176	Intermediate Similarity	NPC470755
0.716	Intermediate Similarity	NPC121200
0.7159	Intermediate Similarity	NPC474232
0.7159	Intermediate Similarity	NPC473311
0.7143	Intermediate Similarity	NPC476012
0.7143	Intermediate Similarity	NPC323498
0.7143	Intermediate Similarity	NPC211752
0.7143	Intermediate Similarity	NPC69469
0.7143	Intermediate Similarity	NPC323597
0.7125	Intermediate Similarity	NPC256640
0.7125	Intermediate Similarity	NPC16279
0.7125	Intermediate Similarity	NPC205615
0.7111	Intermediate Similarity	NPC472198
0.7108	Intermediate Similarity	NPC112868
0.7108	Intermediate Similarity	NPC316844
0.7108	Intermediate Similarity	NPC150502
0.7108	Intermediate Similarity	NPC474894
0.7108	Intermediate Similarity	NPC88735
0.7108	Intermediate Similarity	NPC236649
0.7108	Intermediate Similarity	NPC21693
0.7105	Intermediate Similarity	NPC475760
0.7093	Intermediate Similarity	NPC472009
0.7093	Intermediate Similarity	NPC69082
0.7093	Intermediate Similarity	NPC279267
0.7093	Intermediate Similarity	NPC208473
0.7093	Intermediate Similarity	NPC278283
0.7089	Intermediate Similarity	NPC227396
0.7089	Intermediate Similarity	NPC315843
0.7089	Intermediate Similarity	NPC474280
0.7073	Intermediate Similarity	NPC201225
0.7073	Intermediate Similarity	NPC471537
0.7067	Intermediate Similarity	NPC201356
0.7067	Intermediate Similarity	NPC328653
0.7067	Intermediate Similarity	NPC276299
0.7059	Intermediate Similarity	NPC163093
0.7051	Intermediate Similarity	NPC472254
0.7051	Intermediate Similarity	NPC320119
0.7051	Intermediate Similarity	NPC477087
0.7051	Intermediate Similarity	NPC477086
0.7045	Intermediate Similarity	NPC14901
0.7045	Intermediate Similarity	NPC130359
0.7037	Intermediate Similarity	NPC40049
0.7024	Intermediate Similarity	NPC7414
0.7013	Intermediate Similarity	NPC475004

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 NPC470435 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	2641
0.2-0.3	3706
0.3-0.4	1944
0.4-0.5	547
0.5-0.6	99
0.6-0.7	49
0.7-0.8	7
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
0.7625	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3197	Phase 1
0.7471	Intermediate Similarity	NPD7983	Approved
0.7375	Intermediate Similarity	NPD4271	Approved
0.7375	Intermediate Similarity	NPD4268	Approved
0.72	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4822	Approved
0.7195	Intermediate Similarity	NPD4819	Approved
0.7195	Intermediate Similarity	NPD4821	Approved
0.7195	Intermediate Similarity	NPD4820	Approved
0.7143	Intermediate Similarity	NPD7154	Phase 3
0.7042	Intermediate Similarity	NPD6109	Phase 1
0.7024	Intermediate Similarity	NPD4269	Approved
0.7024	Intermediate Similarity	NPD4270	Approved
0.7011	Intermediate Similarity	NPD4251	Approved
0.7011	Intermediate Similarity	NPD4250	Approved
0.6988	Remote Similarity	NPD4252	Approved
0.6897	Remote Similarity	NPD4249	Approved
0.6897	Remote Similarity	NPD5786	Approved
0.6813	Remote Similarity	NPD5778	Approved
0.6813	Remote Similarity	NPD5779	Approved
0.6782	Remote Similarity	NPD5363	Approved
0.6778	Remote Similarity	NPD6698	Approved
0.6778	Remote Similarity	NPD46	Approved
0.6778	Remote Similarity	NPD7838	Discovery
0.6744	Remote Similarity	NPD5362	Discontinued
0.6714	Remote Similarity	NPD4266	Approved
0.6714	Remote Similarity	NPD3196	Approved
0.6714	Remote Similarity	NPD3194	Approved
0.6714	Remote Similarity	NPD3195	Phase 2
0.6706	Remote Similarity	NPD5369	Approved
0.6703	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD5370	Suspended
0.6628	Remote Similarity	NPD6435	Approved
0.6596	Remote Similarity	NPD7839	Suspended
0.6593	Remote Similarity	NPD5785	Approved
0.6571	Remote Similarity	NPD3172	Approved
0.6552	Remote Similarity	NPD5332	Approved
0.6552	Remote Similarity	NPD5331	Approved
0.6548	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4790	Discontinued
0.6484	Remote Similarity	NPD6101	Approved
0.6484	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD3730	Approved
0.6479	Remote Similarity	NPD3728	Approved
0.6458	Remote Similarity	NPD4225	Approved
0.6404	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5368	Approved
0.6351	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6411	Approved
0.6324	Remote Similarity	NPD5343	Approved
0.6289	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD28	Approved
0.6286	Remote Similarity	NPD29	Approved
0.6269	Remote Similarity	NPD39	Approved
0.6235	Remote Similarity	NPD4756	Discovery
0.6232	Remote Similarity	NPD3173	Approved
0.6163	Remote Similarity	NPD3732	Approved
0.6162	Remote Similarity	NPD5344	Discontinued
0.6154	Remote Similarity	NPD6371	Approved
0.6146	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD6097	Approved
0.6119	Remote Similarity	NPD6096	Approved
0.6118	Remote Similarity	NPD819	Approved
0.6118	Remote Similarity	NPD818	Approved
0.6111	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD6927	Phase 3
0.6029	Remote Similarity	NPD4222	Approved
0.6019	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.597	Remote Similarity	NPD5326	Phase 3
0.5943	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD5209	Approved
0.5875	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD622	Approved
0.5849	Remote Similarity	NPD6421	Discontinued
0.5823	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD7115	Discovery
0.5814	Remote Similarity	NPD8039	Approved
0.5797	Remote Similarity	NPD4265	Approved
0.5797	Remote Similarity	NPD3174	Discontinued
0.5752	Remote Similarity	NPD8516	Approved
0.5752	Remote Similarity	NPD8513	Phase 3
0.5752	Remote Similarity	NPD8517	Approved
0.5752	Remote Similarity	NPD8515	Approved
0.5743	Remote Similarity	NPD6648	Approved
0.5714	Remote Similarity	NPD9119	Approved
0.5714	Remote Similarity	NPD69	Approved
0.566	Remote Similarity	NPD6686	Approved
0.5652	Remote Similarity	NPD6110	Phase 1
0.5638	Remote Similarity	NPD6422	Discontinued
0.5634	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD8444	Approved
0.5612	Remote Similarity	NPD6399	Phase 3
0.561	Remote Similarity	NPD3704	Approved
0.5603	Remote Similarity	NPD8340	Approved
0.5603	Remote Similarity	NPD8341	Approved
0.5603	Remote Similarity	NPD8342	Approved
0.5603	Remote Similarity	NPD8299	Approved
0.56	Remote Similarity	NPD4228	Discovery

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