NPASS Compound

Structure

CID40608 OpenBabel06191715372D 29 33 0 0 1 0 0 0 0 0999 V2000 2.1237 -0.5758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2927 1.0443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9190 2.1253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8001 2.1253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7865 -1.3623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -1.8164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1460 -0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7865 -0.4541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3255 -0.2954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2407 -0.5758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9019 0.5064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7865 -0.4541 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3595 -0.4541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1460 0.9081 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7865 1.3622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5730 0.9081 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9082 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3595 1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7866 -1.3623 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5730 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1724 -0.1010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3595 -1.3353 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7865 2.2434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7631 1.3488 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5277 -1.7902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0255 0.1088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2406 0.5759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 11 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 20 1 0 0 0 0 7 13 1 0 0 0 0 8 20 1 0 0 0 0 9 28 1 0 0 0 0 10 18 1 0 0 0 0 10 20 1 0 0 0 0 11 23 2 0 0 0 0 11 29 1 0 0 0 0 12 21 1 1 0 0 0 12 22 1 0 0 0 0 13 22 1 0 0 0 0 13 24 2 0 0 0 0 14 7 1 6 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 17 1 0 0 0 0 15 25 1 6 0 0 0 16 19 1 0 0 0 0 16 22 1 1 0 0 0 17 21 1 0 0 0 0 17 26 2 0 0 0 0 18 21 1 6 0 0 0 18 29 1 0 0 0 0 20 27 1 1 0 0 0 21 8 1 1 0 0 0 22 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.18
Volume:	397.272
LogP:	1.369
LogD:	0.682
LogS:	-3.391
# Rotatable Bonds:	2
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.495
Synthetic Accessibility Score:	7.132
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.385
MDCK Permeability:	6.3331812270917e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.802
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.423
Plasma Protein Binding (PPB):	42.025787353515625%
Volume Distribution (VD):	0.872
Pgp-substrate:	63.2729606628418%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.698
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.592
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.091
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	3.287
Half-life (T1/2):	0.085

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.708
Drug-inuced Liver Injury (DILI):	0.659
AMES Toxicity:	0.959
Rat Oral Acute Toxicity:	0.967
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.56
Carcinogencity:	0.447
Eye Corrosion:	0.569
Eye Irritation:	0.023
Respiratory Toxicity:	0.99

Download Data

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

Natural Product: NPC40608

Natural Product ID:	NPC40608
*Common Name:**	Laxiflorin M
IUPAC Name:	n.a.
Synonyms:	laxiflorin M
Standard InCHIKey:	SKMNKANUBIXNBF-UEVALPNXSA-N
Standard InCHI:	InChI=1S/C22H28O7/c1-10-18(29-11(2)23)21-8-20(10,27)6-5-12(21)22-9-28-14(7-13(22)24)19(3,4)16(22)15(25)17(21)26/h12,14-16,18,25,27H,1,5-9H2,2-4H3/t12-,14-,15+,16-,18-,20+,21-,22-/m1/s1
SMILES:	CC(=O)O[C@@H]1C(=C)[C@]2(C[C@]31C(=O)[C@@H](O)[C@H]1[C@@]4([C@@H]3CC2)CO[C@@H](C1(C)C)CC4=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517331
PubChem CID:	12967179
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO1927.1	Isodon eriocalyx var. laxiflora	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502334]
NPO1927.1	Isodon eriocalyx var. laxiflora	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1927.1	Isodon eriocalyx var. laxiflora	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
NPT111	Cell Line	K562	Homo sapiens	IC50	=	218.69	ug.mL-1	PMID[492553]

☑ 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 NPC40608 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	298
0.1-0.2	2092
0.2-0.3	6150
0.3-0.4	10643
0.4-0.5	10494
0.5-0.6	6189
0.6-0.7	4566
0.7-0.8	2121
0.8-0.85	130
0.85-0.9	12
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9223	High Similarity	NPC266
0.8868	High Similarity	NPC295366
0.8868	High Similarity	NPC28791
0.8868	High Similarity	NPC37600
0.8857	High Similarity	NPC469985
0.8846	High Similarity	NPC295276
0.8785	High Similarity	NPC251824
0.8785	High Similarity	NPC86852
0.8785	High Similarity	NPC471246
0.8774	High Similarity	NPC47281
0.8762	High Similarity	NPC170615
0.8692	High Similarity	NPC50535
0.8667	High Similarity	NPC39683
0.8667	High Similarity	NPC253886
0.8667	High Similarity	NPC121218
0.8636	High Similarity	NPC94650
0.8598	High Similarity	NPC474558
0.8505	High Similarity	NPC139347
0.8505	High Similarity	NPC216114
0.8468	Intermediate Similarity	NPC56025
0.8426	Intermediate Similarity	NPC98603
0.8426	Intermediate Similarity	NPC84928
0.8393	Intermediate Similarity	NPC476964
0.8378	Intermediate Similarity	NPC255655
0.8378	Intermediate Similarity	NPC124053
0.8349	Intermediate Similarity	NPC285927
0.8333	Intermediate Similarity	NPC87927
0.8319	Intermediate Similarity	NPC285086
0.8318	Intermediate Similarity	NPC289148
0.8318	Intermediate Similarity	NPC46848
0.8318	Intermediate Similarity	NPC163963
0.8318	Intermediate Similarity	NPC52899
0.8304	Intermediate Similarity	NPC471251
0.8302	Intermediate Similarity	NPC471038
0.8302	Intermediate Similarity	NPC109059
0.8302	Intermediate Similarity	NPC288
0.8302	Intermediate Similarity	NPC474793
0.8288	Intermediate Similarity	NPC471250
0.8286	Intermediate Similarity	NPC470387
0.8273	Intermediate Similarity	NPC176949
0.8273	Intermediate Similarity	NPC201908
0.8269	Intermediate Similarity	NPC280804
0.8257	Intermediate Similarity	NPC202793
0.8241	Intermediate Similarity	NPC148628
0.8241	Intermediate Similarity	NPC246736
0.8241	Intermediate Similarity	NPC286519
0.8241	Intermediate Similarity	NPC275990
0.8241	Intermediate Similarity	NPC309388
0.8241	Intermediate Similarity	NPC475803
0.8241	Intermediate Similarity	NPC88203
0.8241	Intermediate Similarity	NPC304832
0.8241	Intermediate Similarity	NPC214946
0.8241	Intermediate Similarity	NPC76866
0.823	Intermediate Similarity	NPC473352
0.8224	Intermediate Similarity	NPC287676
0.8224	Intermediate Similarity	NPC108371
0.8214	Intermediate Similarity	NPC98633
0.8214	Intermediate Similarity	NPC471093
0.8214	Intermediate Similarity	NPC130302
0.8198	Intermediate Similarity	NPC211224
0.8198	Intermediate Similarity	NPC63841
0.819	Intermediate Similarity	NPC470232
0.8173	Intermediate Similarity	NPC199543
0.8165	Intermediate Similarity	NPC96217
0.8155	Intermediate Similarity	NPC100313
0.8148	Intermediate Similarity	NPC148279
0.8148	Intermediate Similarity	NPC236585
0.8148	Intermediate Similarity	NPC14634
0.8148	Intermediate Similarity	NPC75941
0.8142	Intermediate Similarity	NPC470311
0.8142	Intermediate Similarity	NPC470281
0.8142	Intermediate Similarity	NPC329953
0.8142	Intermediate Similarity	NPC29505
0.8136	Intermediate Similarity	NPC470921
0.8131	Intermediate Similarity	NPC98837
0.8131	Intermediate Similarity	NPC38296
0.8131	Intermediate Similarity	NPC28864
0.8131	Intermediate Similarity	NPC474724
0.8131	Intermediate Similarity	NPC78427
0.8131	Intermediate Similarity	NPC16911
0.8131	Intermediate Similarity	NPC89099
0.8131	Intermediate Similarity	NPC469986
0.8131	Intermediate Similarity	NPC20479
0.8131	Intermediate Similarity	NPC38471
0.8131	Intermediate Similarity	NPC162459
0.8125	Intermediate Similarity	NPC470615
0.8115	Intermediate Similarity	NPC221414
0.8113	Intermediate Similarity	NPC13949
0.8113	Intermediate Similarity	NPC329910
0.8113	Intermediate Similarity	NPC29410
0.8113	Intermediate Similarity	NPC200054
0.8108	Intermediate Similarity	NPC186054
0.8095	Intermediate Similarity	NPC470386
0.8095	Intermediate Similarity	NPC470385
0.8095	Intermediate Similarity	NPC475118
0.8091	Intermediate Similarity	NPC29705
0.8077	Intermediate Similarity	NPC198054
0.8056	Intermediate Similarity	NPC156324
0.8056	Intermediate Similarity	NPC470388
0.8056	Intermediate Similarity	NPC37047
0.8056	Intermediate Similarity	NPC55503
0.8056	Intermediate Similarity	NPC293866
0.8056	Intermediate Similarity	NPC41971
0.8056	Intermediate Similarity	NPC267921
0.8056	Intermediate Similarity	NPC180733
0.8037	Intermediate Similarity	NPC10864
0.8037	Intermediate Similarity	NPC253586
0.8036	Intermediate Similarity	NPC94529
0.8036	Intermediate Similarity	NPC218123
0.8036	Intermediate Similarity	NPC469733
0.8036	Intermediate Similarity	NPC471094
0.8036	Intermediate Similarity	NPC208461
0.8036	Intermediate Similarity	NPC473410
0.8036	Intermediate Similarity	NPC112895
0.8036	Intermediate Similarity	NPC231278
0.8036	Intermediate Similarity	NPC469984
0.8036	Intermediate Similarity	NPC55973
0.8036	Intermediate Similarity	NPC469729
0.8036	Intermediate Similarity	NPC289702
0.8036	Intermediate Similarity	NPC232133
0.8034	Intermediate Similarity	NPC471249
0.8019	Intermediate Similarity	NPC98639
0.8019	Intermediate Similarity	NPC470229
0.8018	Intermediate Similarity	NPC12823
0.8018	Intermediate Similarity	NPC4115
0.8018	Intermediate Similarity	NPC138908
0.8018	Intermediate Similarity	NPC200957
0.8018	Intermediate Similarity	NPC265127
0.8	Intermediate Similarity	NPC9848
0.8	Intermediate Similarity	NPC209298
0.8	Intermediate Similarity	NPC312017
0.8	Intermediate Similarity	NPC471252
0.8	Intermediate Similarity	NPC476189
0.8	Intermediate Similarity	NPC122811
0.8	Intermediate Similarity	NPC277074
0.7983	Intermediate Similarity	NPC470779
0.7982	Intermediate Similarity	NPC472003
0.7982	Intermediate Similarity	NPC270586
0.7982	Intermediate Similarity	NPC471790
0.7982	Intermediate Similarity	NPC213320
0.7965	Intermediate Similarity	NPC469983
0.7965	Intermediate Similarity	NPC102741
0.7963	Intermediate Similarity	NPC26270
0.7949	Intermediate Similarity	NPC470171
0.7949	Intermediate Similarity	NPC470778
0.7949	Intermediate Similarity	NPC146432
0.7946	Intermediate Similarity	NPC96333
0.7946	Intermediate Similarity	NPC67745
0.7946	Intermediate Similarity	NPC470952
0.7946	Intermediate Similarity	NPC471474
0.7946	Intermediate Similarity	NPC469746
0.7946	Intermediate Similarity	NPC166993
0.7946	Intermediate Similarity	NPC88833
0.7946	Intermediate Similarity	NPC471461
0.7944	Intermediate Similarity	NPC223169
0.7944	Intermediate Similarity	NPC140242
0.7944	Intermediate Similarity	NPC234564
0.7944	Intermediate Similarity	NPC165616
0.7934	Intermediate Similarity	NPC476729
0.7931	Intermediate Similarity	NPC299849
0.7931	Intermediate Similarity	NPC300051
0.7928	Intermediate Similarity	NPC13149
0.7925	Intermediate Similarity	NPC469982
0.7925	Intermediate Similarity	NPC3359
0.7925	Intermediate Similarity	NPC47853
0.7917	Intermediate Similarity	NPC269642
0.7917	Intermediate Similarity	NPC312833
0.7913	Intermediate Similarity	NPC474927
0.7913	Intermediate Similarity	NPC126691
0.7913	Intermediate Similarity	NPC476163
0.7913	Intermediate Similarity	NPC473397
0.7909	Intermediate Similarity	NPC164551
0.7909	Intermediate Similarity	NPC272472
0.7905	Intermediate Similarity	NPC250753
0.7905	Intermediate Similarity	NPC130840
0.7905	Intermediate Similarity	NPC211403
0.7905	Intermediate Similarity	NPC198242
0.7899	Intermediate Similarity	NPC476962
0.7899	Intermediate Similarity	NPC109973
0.7895	Intermediate Similarity	NPC320383
0.7895	Intermediate Similarity	NPC85391
0.7895	Intermediate Similarity	NPC137104
0.7895	Intermediate Similarity	NPC474786
0.7895	Intermediate Similarity	NPC473324
0.789	Intermediate Similarity	NPC94906
0.7881	Intermediate Similarity	NPC470776
0.7881	Intermediate Similarity	NPC113448
0.7876	Intermediate Similarity	NPC189663
0.7876	Intermediate Similarity	NPC89860
0.7876	Intermediate Similarity	NPC273155
0.787	Intermediate Similarity	NPC190080
0.787	Intermediate Similarity	NPC111187
0.7864	Intermediate Similarity	NPC472495
0.7864	Intermediate Similarity	NPC472497
0.7863	Intermediate Similarity	NPC469794
0.7863	Intermediate Similarity	NPC89929
0.7863	Intermediate Similarity	NPC72772
0.7863	Intermediate Similarity	NPC213084
0.7863	Intermediate Similarity	NPC190185
0.7857	Intermediate Similarity	NPC307660

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 NPC40608 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	2452
0.2-0.3	3914
0.3-0.4	1587
0.4-0.5	485
0.5-0.6	225
0.6-0.7	145
0.7-0.8	48
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
0.8036	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD6675	Approved
0.7699	Intermediate Similarity	NPD6402	Approved
0.7699	Intermediate Similarity	NPD7128	Approved
0.7699	Intermediate Similarity	NPD5739	Approved
0.7652	Intermediate Similarity	NPD6372	Approved
0.7652	Intermediate Similarity	NPD6373	Approved
0.7632	Intermediate Similarity	NPD5697	Approved
0.7632	Intermediate Similarity	NPD5701	Approved
0.7603	Intermediate Similarity	NPD6319	Approved
0.7565	Intermediate Similarity	NPD7320	Approved
0.7565	Intermediate Similarity	NPD6881	Approved
0.7565	Intermediate Similarity	NPD6899	Approved
0.7542	Intermediate Similarity	NPD8133	Approved
0.754	Intermediate Similarity	NPD7319	Approved
0.7521	Intermediate Similarity	NPD6650	Approved
0.7521	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD6013	Approved
0.75	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD6014	Approved
0.746	Intermediate Similarity	NPD7736	Approved
0.744	Intermediate Similarity	NPD7507	Approved
0.7436	Intermediate Similarity	NPD7102	Approved
0.7436	Intermediate Similarity	NPD7290	Approved
0.7436	Intermediate Similarity	NPD6883	Approved
0.7434	Intermediate Similarity	NPD5211	Phase 2
0.7414	Intermediate Similarity	NPD6011	Approved
0.7411	Intermediate Similarity	NPD7640	Approved
0.7411	Intermediate Similarity	NPD7639	Approved
0.7407	Intermediate Similarity	NPD8035	Phase 2
0.7407	Intermediate Similarity	NPD8034	Phase 2
0.7395	Intermediate Similarity	NPD4632	Approved
0.7387	Intermediate Similarity	NPD4755	Approved
0.7373	Intermediate Similarity	NPD6617	Approved
0.7373	Intermediate Similarity	NPD6869	Approved
0.7373	Intermediate Similarity	NPD6847	Approved
0.7373	Intermediate Similarity	NPD8130	Phase 1
0.736	Intermediate Similarity	NPD7492	Approved
0.7321	Intermediate Similarity	NPD7638	Approved
0.7321	Intermediate Similarity	NPD5696	Approved
0.7317	Intermediate Similarity	NPD6054	Approved
0.7317	Intermediate Similarity	NPD6059	Approved
0.7311	Intermediate Similarity	NPD8297	Approved
0.7311	Intermediate Similarity	NPD6882	Approved
0.7304	Intermediate Similarity	NPD5141	Approved
0.7302	Intermediate Similarity	NPD6616	Approved
0.7288	Intermediate Similarity	NPD4634	Approved
0.7258	Intermediate Similarity	NPD6016	Approved
0.7258	Intermediate Similarity	NPD6015	Approved
0.7258	Intermediate Similarity	NPD6921	Approved
0.7257	Intermediate Similarity	NPD5286	Approved
0.7257	Intermediate Similarity	NPD5285	Approved
0.7257	Intermediate Similarity	NPD4700	Approved
0.7257	Intermediate Similarity	NPD4696	Approved
0.7244	Intermediate Similarity	NPD7078	Approved
0.7244	Intermediate Similarity	NPD8293	Discontinued
0.7241	Intermediate Similarity	NPD6008	Approved
0.7227	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7115	Discovery
0.7213	Intermediate Similarity	NPD6009	Approved
0.72	Intermediate Similarity	NPD6370	Approved
0.72	Intermediate Similarity	NPD5988	Approved
0.717	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8328	Phase 3
0.7131	Intermediate Similarity	NPD6274	Approved
0.713	Intermediate Similarity	NPD5225	Approved
0.713	Intermediate Similarity	NPD5224	Approved
0.713	Intermediate Similarity	NPD5226	Approved
0.713	Intermediate Similarity	NPD4633	Approved
0.712	Intermediate Similarity	NPD5983	Phase 2
0.708	Intermediate Similarity	NPD6084	Phase 2
0.708	Intermediate Similarity	NPD6083	Phase 2
0.7073	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5174	Approved
0.7069	Intermediate Similarity	NPD5175	Approved
0.7043	Intermediate Similarity	NPD5223	Approved
0.7008	Intermediate Similarity	NPD7604	Phase 2
0.6983	Remote Similarity	NPD7632	Discontinued
0.696	Remote Similarity	NPD7101	Approved
0.696	Remote Similarity	NPD7100	Approved
0.6949	Remote Similarity	NPD4767	Approved
0.6949	Remote Similarity	NPD4768	Approved
0.6935	Remote Similarity	NPD6317	Approved
0.6923	Remote Similarity	NPD4754	Approved
0.6903	Remote Similarity	NPD5210	Approved
0.6903	Remote Similarity	NPD4629	Approved
0.6903	Remote Similarity	NPD5695	Phase 3
0.6899	Remote Similarity	NPD6336	Discontinued
0.6897	Remote Similarity	NPD1700	Approved
0.6885	Remote Similarity	NPD6053	Discontinued
0.688	Remote Similarity	NPD6313	Approved
0.688	Remote Similarity	NPD6314	Approved
0.688	Remote Similarity	NPD7328	Approved
0.688	Remote Similarity	NPD6335	Approved
0.688	Remote Similarity	NPD7327	Approved
0.6875	Remote Similarity	NPD6399	Phase 3
0.685	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6908	Approved
0.685	Remote Similarity	NPD6909	Approved
0.685	Remote Similarity	NPD8033	Approved
0.6842	Remote Similarity	NPD4697	Phase 3
0.6833	Remote Similarity	NPD4729	Approved
0.6833	Remote Similarity	NPD5128	Approved
0.6833	Remote Similarity	NPD4730	Approved
0.6825	Remote Similarity	NPD7516	Approved
0.6794	Remote Similarity	NPD6033	Approved
0.6786	Remote Similarity	NPD5693	Phase 1
0.6783	Remote Similarity	NPD7902	Approved
0.6777	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8377	Approved
0.6772	Remote Similarity	NPD8294	Approved
0.6757	Remote Similarity	NPD4753	Phase 2
0.675	Remote Similarity	NPD6412	Phase 2
0.6726	Remote Similarity	NPD4202	Approved
0.6724	Remote Similarity	NPD4225	Approved
0.6721	Remote Similarity	NPD5251	Approved
0.6721	Remote Similarity	NPD5250	Approved
0.6721	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5248	Approved
0.6721	Remote Similarity	NPD5249	Phase 3
0.6721	Remote Similarity	NPD5247	Approved
0.6719	Remote Similarity	NPD8335	Approved
0.6719	Remote Similarity	NPD8380	Approved
0.6719	Remote Similarity	NPD8378	Approved
0.6719	Remote Similarity	NPD8379	Approved
0.6719	Remote Similarity	NPD8296	Approved
0.6696	Remote Similarity	NPD5221	Approved
0.6696	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5222	Approved
0.6667	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD6114	Approved
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD6118	Approved
0.6667	Remote Similarity	NPD6115	Approved
0.6667	Remote Similarity	NPD5217	Approved
0.6667	Remote Similarity	NPD6697	Approved
0.6667	Remote Similarity	NPD5216	Approved
0.6639	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5173	Approved
0.6637	Remote Similarity	NPD7515	Phase 2
0.6607	Remote Similarity	NPD5328	Approved
0.6589	Remote Similarity	NPD8516	Approved
0.6589	Remote Similarity	NPD8515	Approved
0.6589	Remote Similarity	NPD8513	Phase 3
0.6589	Remote Similarity	NPD8517	Approved
0.6585	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6371	Approved
0.6585	Remote Similarity	NPD5169	Approved
0.6585	Remote Similarity	NPD5135	Approved
0.6583	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6116	Phase 1
0.6557	Remote Similarity	NPD6686	Approved
0.6538	Remote Similarity	NPD3702	Approved
0.6538	Remote Similarity	NPD3703	Phase 2
0.6532	Remote Similarity	NPD5127	Approved
0.6522	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7900	Approved
0.6518	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6079	Approved
0.6491	Remote Similarity	NPD6411	Approved
0.6486	Remote Similarity	NPD6098	Approved
0.6486	Remote Similarity	NPD3618	Phase 1
0.6476	Remote Similarity	NPD6117	Approved
0.6475	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6334	Approved
0.6475	Remote Similarity	NPD6333	Approved
0.6466	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD7503	Approved
0.646	Remote Similarity	NPD6080	Approved
0.646	Remote Similarity	NPD6673	Approved
0.646	Remote Similarity	NPD6904	Approved
0.6457	Remote Similarity	NPD6868	Approved
0.6435	Remote Similarity	NPD5778	Approved
0.6435	Remote Similarity	NPD5779	Approved
0.6429	Remote Similarity	NPD3573	Approved
0.6397	Remote Similarity	NPD7260	Phase 2
0.6379	Remote Similarity	NPD5282	Discontinued
0.6378	Remote Similarity	NPD5167	Approved
0.6372	Remote Similarity	NPD6672	Approved
0.6372	Remote Similarity	NPD5737	Approved
0.6348	Remote Similarity	NPD7637	Suspended
0.6348	Remote Similarity	NPD5284	Approved
0.6348	Remote Similarity	NPD5281	Approved
0.6339	Remote Similarity	NPD6684	Approved
0.6339	Remote Similarity	NPD5330	Approved
0.6339	Remote Similarity	NPD7521	Approved
0.6339	Remote Similarity	NPD7334	Approved
0.6339	Remote Similarity	NPD6409	Approved
0.6339	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7146	Approved
0.6325	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6101	Approved
0.6316	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD3665	Phase 1
0.6306	Remote Similarity	NPD3133	Approved
0.6306	Remote Similarity	NPD4786	Approved
0.6306	Remote Similarity	NPD3666	Approved
0.6306	Remote Similarity	NPD4197	Approved
0.6286	Remote Similarity	NPD6113	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