NPASS Compound

Structure

CID78836 OpenBabel06191715412D 29 34 0 0 1 0 0 0 0 0999 V2000 -2.6947 -2.4407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4773 -3.4497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7061 -0.2217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0125 0.1917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1738 -1.8773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3913 -1.2050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5125 -2.1264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5427 -2.0194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1114 -1.8967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2312 -3.0051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3536 -1.5896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3646 -2.4954 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3556 -1.6928 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2975 -0.5532 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9131 -1.4913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2807 0.0739 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4752 -0.6278 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0083 -0.7366 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0013 -0.6157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1677 -1.3963 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1456 -1.2367 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1315 0.0128 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4931 -2.5696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4141 -0.9179 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0166 0.8246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8197 0.3384 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2769 -2.9960 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8395 -0.3192 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 9 2 0 0 0 0 2 10 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 7 1 0 0 0 0 6 19 1 0 0 0 0 8 12 1 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 23 2 0 0 0 0 10 27 1 0 0 0 0 11 8 1 1 0 0 0 11 17 1 0 0 0 0 12 13 1 0 0 0 0 12 27 1 1 0 0 0 13 20 1 6 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 6 0 0 0 15 21 1 0 0 0 0 15 24 2 0 0 0 0 16 22 1 1 0 0 0 16 25 1 0 0 0 0 17 21 1 6 0 0 0 17 28 1 0 0 0 0 18 20 1 1 0 0 0 18 28 1 0 0 0 0 18 29 1 0 0 0 0 20 7 1 6 0 0 0 21 22 1 1 0 0 0 22 26 1 1 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.18
Volume:	391.352
LogP:	2.345
LogD:	2.234
LogS:	-4.652
# Rotatable Bonds:	2
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.502
Synthetic Accessibility Score:	7.474
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.368
MDCK Permeability:	1.4580649803974666e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.882
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.678

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.678
Plasma Protein Binding (PPB):	51.59285354614258%
Volume Distribution (VD):	1.252
Pgp-substrate:	65.48371887207031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.52
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.603
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.039
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	2.36
Half-life (T1/2):	0.246

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.125
Drug-inuced Liver Injury (DILI):	0.148
AMES Toxicity:	0.661
Rat Oral Acute Toxicity:	0.961
Maximum Recommended Daily Dose:	0.455
Skin Sensitization:	0.561
Carcinogencity:	0.865
Eye Corrosion:	0.041
Eye Irritation:	0.026
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC78836

Natural Product ID:	NPC78836
*Common Name:**	Xerophilusin A
IUPAC Name:	n.a.
Synonyms:	Xerophilusin A
Standard InCHIKey:	AFBNZCDGSSSCST-LKXIHEMSSA-N
Standard InCHI:	InChI=1S/C22H28O7/c1-9-11-8-12(27-10(2)23)13-20-7-5-6-19(3,4)14(20)16(25)22(26)21(13,15(9)24)17(11)28-18(20)29-22/h11-14,16-18,25-26H,1,5-8H2,2-4H3/t11-,12-,13-,14+,16-,17+,18-,20+,21-,22-/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@H]2C(=C)C(=O)[C@@]34[C@@H]1[C@@]15CCCC([C@H]5[C@@H]([C@@]4(O[C@@H]1O[C@H]23)O)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL404203
PubChem CID:	44445773
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
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843567]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17665952]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33325237]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	9
Others	3

Activity Type	# Activity
Cell Line	11
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	1600.0	nM	PMID[489176]
NPT1097	Cell Line	MKN-45	Homo sapiens	IC50	>	10000.0	nM	PMID[489176]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[489176]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	2.22	ug.mL-1	PMID[489177]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	0.45	ug.mL-1	PMID[489177]
NPT1179	Cell Line	MKN-28	Homo sapiens	IC50	=	0.12	ug.mL-1	PMID[489177]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	97.5	%	PMID[489178]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	11300.0	nM	PMID[489178]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	600.0	nM	PMID[489178]
NPT2	Others	Unspecified		IC50	=	1800.0	nM	PMID[489178]

☑ 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 NPC78836 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	312
0.1-0.2	2129
0.2-0.3	6146
0.3-0.4	10543
0.4-0.5	10223
0.5-0.6	6408
0.6-0.7	3942
0.7-0.8	2100
0.8-0.85	729
0.85-0.9	94
0.9-0.95	43
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
0.9907	High Similarity	NPC229752
0.9813	High Similarity	NPC17165
0.972	High Similarity	NPC94141
0.9626	High Similarity	NPC157929
0.9541	High Similarity	NPC88945
0.9537	High Similarity	NPC132668
0.9533	High Similarity	NPC63244
0.9455	High Similarity	NPC473304
0.9444	High Similarity	NPC473303
0.9444	High Similarity	NPC473397
0.9444	High Similarity	NPC145625
0.9444	High Similarity	NPC471244
0.9439	High Similarity	NPC471476
0.9358	High Similarity	NPC471248
0.9352	High Similarity	NPC122339
0.9352	High Similarity	NPC29505
0.9352	High Similarity	NPC213320
0.9346	High Similarity	NPC102741
0.9346	High Similarity	NPC118721
0.9346	High Similarity	NPC252679
0.9266	High Similarity	NPC471245
0.9266	High Similarity	NPC473352
0.9266	High Similarity	NPC474927
0.9259	High Similarity	NPC473324
0.9259	High Similarity	NPC471093
0.9252	High Similarity	NPC189663
0.9252	High Similarity	NPC89860
0.9252	High Similarity	NPC473410
0.9252	High Similarity	NPC469984
0.9252	High Similarity	NPC471094
0.9182	High Similarity	NPC471252
0.9174	High Similarity	NPC329953
0.9167	High Similarity	NPC469744
0.9159	High Similarity	NPC469746
0.9159	High Similarity	NPC471474
0.9083	High Similarity	NPC474786
0.9083	High Similarity	NPC85391
0.9083	High Similarity	NPC137104
0.9083	High Similarity	NPC320383
0.9074	High Similarity	NPC63841
0.9074	High Similarity	NPC469733
0.9074	High Similarity	NPC55973
0.9074	High Similarity	NPC469729
0.9065	High Similarity	NPC56656
0.9065	High Similarity	NPC130511
0.9065	High Similarity	NPC307660
0.8991	High Similarity	NPC131903
0.8991	High Similarity	NPC274827
0.8981	High Similarity	NPC67745
0.8981	High Similarity	NPC471461
0.8981	High Similarity	NPC186054
0.8972	High Similarity	NPC202793
0.8929	High Similarity	NPC243354
0.8899	High Similarity	NPC232133
0.8889	High Similarity	NPC12823
0.8839	High Similarity	NPC194273
0.8829	High Similarity	NPC56025
0.8818	High Similarity	NPC469983
0.8727	High Similarity	NPC231278
0.8727	High Similarity	NPC218123
0.8727	High Similarity	NPC112895
0.8704	High Similarity	NPC139347
0.8692	High Similarity	NPC14634
0.8661	High Similarity	NPC471243
0.8636	High Similarity	NPC88833
0.8636	High Similarity	NPC96333
0.8624	High Similarity	NPC474558
0.8611	High Similarity	NPC475803
0.8611	High Similarity	NPC309388
0.8584	High Similarity	NPC472719
0.8584	High Similarity	NPC207845
0.8571	High Similarity	NPC49730
0.8571	High Similarity	NPC98069
0.8559	High Similarity	NPC273155
0.8545	High Similarity	NPC4115
0.8545	High Similarity	NPC103172
0.8545	High Similarity	NPC164600
0.8532	High Similarity	NPC277074
0.8532	High Similarity	NPC209298
0.8532	High Similarity	NPC87927
0.8522	High Similarity	NPC472718
0.8509	High Similarity	NPC73986
0.8509	High Similarity	NPC146563
0.8509	High Similarity	NPC320118
0.85	High Similarity	NPC273962
0.8496	Intermediate Similarity	NPC11035
0.8496	Intermediate Similarity	NPC274833
0.8475	Intermediate Similarity	NPC470478
0.8468	Intermediate Similarity	NPC61071
0.8468	Intermediate Similarity	NPC166993
0.8455	Intermediate Similarity	NPC101842
0.8455	Intermediate Similarity	NPC13149
0.8448	Intermediate Similarity	NPC156651
0.8435	Intermediate Similarity	NPC54395
0.8426	Intermediate Similarity	NPC470388
0.8421	Intermediate Similarity	NPC470543
0.8417	Intermediate Similarity	NPC248202
0.8378	Intermediate Similarity	NPC200957
0.8378	Intermediate Similarity	NPC138908
0.8364	Intermediate Similarity	NPC122811
0.8364	Intermediate Similarity	NPC107385
0.8362	Intermediate Similarity	NPC137414
0.8362	Intermediate Similarity	NPC469820
0.8362	Intermediate Similarity	NPC469823
0.8349	Intermediate Similarity	NPC163963
0.8349	Intermediate Similarity	NPC52899
0.8349	Intermediate Similarity	NPC471790
0.8349	Intermediate Similarity	NPC289148
0.8347	Intermediate Similarity	NPC47113
0.8347	Intermediate Similarity	NPC174367
0.8333	Intermediate Similarity	NPC1876
0.8333	Intermediate Similarity	NPC474793
0.8333	Intermediate Similarity	NPC240734
0.8333	Intermediate Similarity	NPC91838
0.8333	Intermediate Similarity	NPC204392
0.8333	Intermediate Similarity	NPC275668
0.8319	Intermediate Similarity	NPC91583
0.8319	Intermediate Similarity	NPC240125
0.8319	Intermediate Similarity	NPC473844
0.8319	Intermediate Similarity	NPC51947
0.8319	Intermediate Similarity	NPC475182
0.8319	Intermediate Similarity	NPC8431
0.8306	Intermediate Similarity	NPC473805
0.8306	Intermediate Similarity	NPC473519
0.8304	Intermediate Similarity	NPC470166
0.8291	Intermediate Similarity	NPC218970
0.8291	Intermediate Similarity	NPC477252
0.8291	Intermediate Similarity	NPC470171
0.8291	Intermediate Similarity	NPC309433
0.8288	Intermediate Similarity	NPC301787
0.8288	Intermediate Similarity	NPC470167
0.8273	Intermediate Similarity	NPC88203
0.8273	Intermediate Similarity	NPC304832
0.8273	Intermediate Similarity	NPC214946
0.8273	Intermediate Similarity	NPC76866
0.8273	Intermediate Similarity	NPC148628
0.8273	Intermediate Similarity	NPC246736
0.8273	Intermediate Similarity	NPC286519
0.8264	Intermediate Similarity	NPC130229
0.8264	Intermediate Similarity	NPC469841
0.8264	Intermediate Similarity	NPC469842
0.8261	Intermediate Similarity	NPC243572
0.8257	Intermediate Similarity	NPC287676
0.8257	Intermediate Similarity	NPC127408
0.8257	Intermediate Similarity	NPC291785
0.825	Intermediate Similarity	NPC156789
0.8246	Intermediate Similarity	NPC98633
0.8246	Intermediate Similarity	NPC130302
0.824	Intermediate Similarity	NPC102015
0.823	Intermediate Similarity	NPC88744
0.822	Intermediate Similarity	NPC469822
0.8214	Intermediate Similarity	NPC222833
0.8214	Intermediate Similarity	NPC285927
0.8198	Intermediate Similarity	NPC96217
0.8198	Intermediate Similarity	NPC216114
0.8198	Intermediate Similarity	NPC473406
0.8198	Intermediate Similarity	NPC471253
0.819	Intermediate Similarity	NPC102619
0.8182	Intermediate Similarity	NPC148279
0.8182	Intermediate Similarity	NPC252614
0.8182	Intermediate Similarity	NPC160084
0.8182	Intermediate Similarity	NPC236585
0.8182	Intermediate Similarity	NPC46848
0.8174	Intermediate Similarity	NPC471251
0.8174	Intermediate Similarity	NPC272242
0.8174	Intermediate Similarity	NPC94650
0.8165	Intermediate Similarity	NPC471038
0.8165	Intermediate Similarity	NPC16911
0.8165	Intermediate Similarity	NPC78427
0.8158	Intermediate Similarity	NPC471250
0.8151	Intermediate Similarity	NPC473401
0.8151	Intermediate Similarity	NPC161738
0.8148	Intermediate Similarity	NPC13949
0.8145	Intermediate Similarity	NPC476966
0.8142	Intermediate Similarity	NPC287269
0.8136	Intermediate Similarity	NPC300419
0.813	Intermediate Similarity	NPC470780
0.8125	Intermediate Similarity	NPC244247
0.8125	Intermediate Similarity	NPC84928
0.8125	Intermediate Similarity	NPC98603
0.812	Intermediate Similarity	NPC469821
0.812	Intermediate Similarity	NPC475633
0.812	Intermediate Similarity	NPC473882
0.8115	Intermediate Similarity	NPC177820
0.8115	Intermediate Similarity	NPC247315
0.8115	Intermediate Similarity	NPC471962
0.8115	Intermediate Similarity	NPC30188
0.8115	Intermediate Similarity	NPC7850
0.8115	Intermediate Similarity	NPC473474
0.8115	Intermediate Similarity	NPC6615
0.8115	Intermediate Similarity	NPC471963
0.8115	Intermediate Similarity	NPC470477
0.8108	Intermediate Similarity	NPC471254
0.8108	Intermediate Similarity	NPC470172
0.8108	Intermediate Similarity	NPC275990
0.8103	Intermediate Similarity	NPC205534
0.8103	Intermediate Similarity	NPC233003
0.8099	Intermediate Similarity	NPC162574
0.8099	Intermediate Similarity	NPC213952
0.8099	Intermediate Similarity	NPC471965

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 NPC78836 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	2478
0.2-0.3	3904
0.3-0.4	1568
0.4-0.5	451
0.5-0.6	271
0.6-0.7	122
0.7-0.8	41
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8034	Intermediate Similarity	NPD8133	Approved
0.8033	Intermediate Similarity	NPD8328	Phase 3
0.7983	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7736	Approved
0.7717	Intermediate Similarity	NPD7319	Approved
0.7672	Intermediate Similarity	NPD6412	Phase 2
0.7661	Intermediate Similarity	NPD6370	Approved
0.7652	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7507	Approved
0.7607	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD8293	Discontinued
0.754	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD6054	Approved
0.748	Intermediate Similarity	NPD6616	Approved
0.744	Intermediate Similarity	NPD6015	Approved
0.744	Intermediate Similarity	NPD6016	Approved
0.7422	Intermediate Similarity	NPD7078	Approved
0.7398	Intermediate Similarity	NPD6009	Approved
0.7381	Intermediate Similarity	NPD5988	Approved
0.736	Intermediate Similarity	NPD8377	Approved
0.736	Intermediate Similarity	NPD6059	Approved
0.736	Intermediate Similarity	NPD8294	Approved
0.7311	Intermediate Similarity	NPD6686	Approved
0.7302	Intermediate Similarity	NPD8335	Approved
0.7302	Intermediate Similarity	NPD8517	Approved
0.7302	Intermediate Similarity	NPD8516	Approved
0.7302	Intermediate Similarity	NPD8378	Approved
0.7302	Intermediate Similarity	NPD8296	Approved
0.7302	Intermediate Similarity	NPD8515	Approved
0.7302	Intermediate Similarity	NPD8513	Phase 3
0.7302	Intermediate Similarity	NPD8033	Approved
0.7302	Intermediate Similarity	NPD8380	Approved
0.7302	Intermediate Similarity	NPD8379	Approved
0.7295	Intermediate Similarity	NPD4632	Approved
0.728	Intermediate Similarity	NPD7516	Approved
0.7213	Intermediate Similarity	NPD6882	Approved
0.72	Intermediate Similarity	NPD7328	Approved
0.72	Intermediate Similarity	NPD7327	Approved
0.712	Intermediate Similarity	NPD7115	Discovery
0.7083	Intermediate Similarity	NPD5697	Approved
0.7073	Intermediate Similarity	NPD8297	Approved
0.7049	Intermediate Similarity	NPD4634	Approved
0.7031	Intermediate Similarity	NPD7503	Approved
0.7025	Intermediate Similarity	NPD6881	Approved
0.7025	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD6675	Approved
0.7	Intermediate Similarity	NPD6008	Approved
0.7	Intermediate Similarity	NPD6402	Approved
0.7	Intermediate Similarity	NPD5739	Approved
0.7	Intermediate Similarity	NPD7128	Approved
0.6992	Remote Similarity	NPD6650	Approved
0.6992	Remote Similarity	NPD6649	Approved
0.6991	Remote Similarity	NPD8035	Phase 2
0.6991	Remote Similarity	NPD8034	Phase 2
0.6967	Remote Similarity	NPD6373	Approved
0.6967	Remote Similarity	NPD6372	Approved
0.6967	Remote Similarity	NPD6014	Approved
0.6967	Remote Similarity	NPD6012	Approved
0.6967	Remote Similarity	NPD6013	Approved
0.6942	Remote Similarity	NPD5701	Approved
0.6911	Remote Similarity	NPD6883	Approved
0.6911	Remote Similarity	NPD7290	Approved
0.6911	Remote Similarity	NPD7102	Approved
0.6899	Remote Similarity	NPD6921	Approved
0.6899	Remote Similarity	NPD5983	Phase 2
0.6885	Remote Similarity	NPD7320	Approved
0.6885	Remote Similarity	NPD6011	Approved
0.6855	Remote Similarity	NPD6847	Approved
0.6855	Remote Similarity	NPD6869	Approved
0.6855	Remote Similarity	NPD8130	Phase 1
0.6855	Remote Similarity	NPD6617	Approved
0.6842	Remote Similarity	NPD6033	Approved
0.6829	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7604	Phase 2
0.6783	Remote Similarity	NPD8171	Discontinued
0.6783	Remote Similarity	NPD6399	Phase 3
0.678	Remote Similarity	NPD4225	Approved
0.6757	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD4696	Approved
0.6723	Remote Similarity	NPD5286	Approved
0.6723	Remote Similarity	NPD5285	Approved
0.6695	Remote Similarity	NPD7902	Approved
0.6695	Remote Similarity	NPD4755	Approved
0.6692	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD6067	Discontinued
0.6641	Remote Similarity	NPD6274	Approved
0.664	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5224	Approved
0.6612	Remote Similarity	NPD5211	Phase 2
0.6612	Remote Similarity	NPD5225	Approved
0.6612	Remote Similarity	NPD5226	Approved
0.6612	Remote Similarity	NPD4633	Approved
0.6587	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4700	Approved
0.6581	Remote Similarity	NPD7748	Approved
0.6557	Remote Similarity	NPD5175	Approved
0.6557	Remote Similarity	NPD5174	Approved
0.6552	Remote Similarity	NPD7515	Phase 2
0.6552	Remote Similarity	NPD6079	Approved
0.6529	Remote Similarity	NPD1700	Approved
0.6529	Remote Similarity	NPD5223	Approved
0.6522	Remote Similarity	NPD5328	Approved
0.6504	Remote Similarity	NPD5141	Approved
0.65	Remote Similarity	NPD7638	Approved
0.6489	Remote Similarity	NPD7101	Approved
0.6489	Remote Similarity	NPD7100	Approved
0.6471	Remote Similarity	NPD4697	Phase 3
0.6471	Remote Similarity	NPD5222	Approved
0.6471	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5221	Approved
0.6462	Remote Similarity	NPD6317	Approved
0.6457	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7640	Approved
0.6446	Remote Similarity	NPD7639	Approved
0.6441	Remote Similarity	NPD7900	Approved
0.6441	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6084	Phase 2
0.6417	Remote Similarity	NPD5173	Approved
0.6417	Remote Similarity	NPD6083	Phase 2
0.6412	Remote Similarity	NPD6313	Approved
0.6412	Remote Similarity	NPD6335	Approved
0.6412	Remote Similarity	NPD6314	Approved
0.641	Remote Similarity	NPD6411	Approved
0.6404	Remote Similarity	NPD3618	Phase 1
0.64	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD8074	Phase 3
0.6396	Remote Similarity	NPD1779	Approved
0.6396	Remote Similarity	NPD1780	Approved
0.6391	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD6940	Discontinued
0.6378	Remote Similarity	NPD6371	Approved
0.6377	Remote Similarity	NPD5956	Approved
0.6364	Remote Similarity	NPD5696	Approved
0.6356	Remote Similarity	NPD4202	Approved
0.6349	Remote Similarity	NPD4730	Approved
0.6349	Remote Similarity	NPD5128	Approved
0.6349	Remote Similarity	NPD4729	Approved
0.6348	Remote Similarity	NPD3573	Approved
0.632	Remote Similarity	NPD4767	Approved
0.632	Remote Similarity	NPD4768	Approved
0.629	Remote Similarity	NPD4754	Approved
0.6286	Remote Similarity	NPD8338	Approved
0.6283	Remote Similarity	NPD3669	Approved
0.6283	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD4788	Approved
0.6273	Remote Similarity	NPD6118	Approved
0.6273	Remote Similarity	NPD6697	Approved
0.6273	Remote Similarity	NPD6114	Approved
0.6273	Remote Similarity	NPD6115	Approved
0.6269	Remote Similarity	NPD6908	Approved
0.6269	Remote Similarity	NPD6909	Approved
0.6261	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.626	Remote Similarity	NPD6868	Approved
0.625	Remote Similarity	NPD5250	Approved
0.625	Remote Similarity	NPD5248	Approved
0.625	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD5249	Phase 3
0.625	Remote Similarity	NPD5247	Approved
0.625	Remote Similarity	NPD5251	Approved
0.6239	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6101	Approved
0.6232	Remote Similarity	NPD8337	Approved
0.6232	Remote Similarity	NPD8336	Approved
0.6228	Remote Similarity	NPD4786	Approved
0.6202	Remote Similarity	NPD5215	Approved
0.6202	Remote Similarity	NPD5216	Approved
0.6202	Remote Similarity	NPD5217	Approved
0.6195	Remote Similarity	NPD3667	Approved
0.6182	Remote Similarity	NPD6116	Phase 1
0.6181	Remote Similarity	NPD6334	Approved
0.6181	Remote Similarity	NPD6333	Approved
0.6154	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6053	Discontinued
0.6147	Remote Similarity	NPD3703	Phase 2
0.6124	Remote Similarity	NPD5135	Approved
0.6124	Remote Similarity	NPD5169	Approved
0.6124	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD7521	Approved
0.6121	Remote Similarity	NPD5330	Approved
0.6121	Remote Similarity	NPD7146	Approved
0.6121	Remote Similarity	NPD7334	Approved
0.6121	Remote Similarity	NPD6409	Approved
0.6121	Remote Similarity	NPD6684	Approved
0.6116	Remote Similarity	NPD5210	Approved
0.6116	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD4629	Approved
0.6116	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD8080	Discontinued
0.6102	Remote Similarity	NPD4753	Phase 2
0.6091	Remote Similarity	NPD6117	Approved
0.609	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD3133	Approved
0.6087	Remote Similarity	NPD3666	Approved
0.6087	Remote Similarity	NPD3665	Phase 1
0.6083	Remote Similarity	NPD5778	Approved
0.6083	Remote Similarity	NPD5779	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