NPASS Compound

Structure

CID145625 OpenBabel06191715502D 26 31 0 0 1 0 0 0 0 0999 V2000 -3.1050 -0.8450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9885 1.4434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4056 2.0974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6765 1.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9286 1.2455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1483 1.8123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9738 1.8421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4743 0.9595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6765 -0.3077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0095 0.3836 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3288 0.7672 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1305 0.7250 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9285 -0.4784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1039 0.4772 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1305 0.0422 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.7672 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2707 1.2015 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6644 1.1507 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3288 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6644 -0.3836 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7755 -1.1484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0186 0.8512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5519 -0.2865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9738 -1.0750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3070 0.6910 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 3 6 1 0 0 0 0 3 7 1 0 0 0 0 4 5 1 0 0 0 0 5 11 1 0 0 0 0 6 17 1 0 0 0 0 8 17 1 0 0 0 0 8 25 1 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 4 1 6 0 0 0 10 14 1 0 0 0 0 11 18 1 1 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 12 17 1 1 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 13 21 2 0 0 0 0 14 19 1 1 0 0 0 14 22 1 0 0 0 0 15 20 1 6 0 0 0 15 23 1 0 0 0 0 16 18 1 1 0 0 0 16 25 1 0 0 0 0 16 26 1 0 0 0 0 17 2 1 6 0 0 0 18 7 1 6 0 0 0 19 20 1 1 0 0 0 20 24 1 1 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	350.606
LogP:	1.167
LogD:	1.072
LogS:	-4.287
# Rotatable Bonds:	0
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.55
Synthetic Accessibility Score:	7.466
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.146
MDCK Permeability:	1.516140309831826e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.924
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.086
30% Bioavailability (F30%):	0.348

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.756
Plasma Protein Binding (PPB):	52.514827728271484%
Volume Distribution (VD):	1.272
Pgp-substrate:	50.672340393066406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.953
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.731
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.182

ADMET: Excretion

Clearance (CL):	1.76
Half-life (T1/2):	0.626

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.188
Drug-inuced Liver Injury (DILI):	0.085
AMES Toxicity:	0.872
Rat Oral Acute Toxicity:	0.923
Maximum Recommended Daily Dose:	0.818
Skin Sensitization:	0.623
Carcinogencity:	0.894
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC145625

Natural Product ID:	NPC145625
*Common Name:**	Xerophilusin D
IUPAC Name:	n.a.
Synonyms:	Xerophilusin D
Standard InCHIKey:	AEKXPCBWZDPSDU-ODPFNFGWSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-9-10-4-5-11-18-7-3-6-17(2)8-25-16(18)26-20(24,15(23)12(17)18)19(11,13(9)21)14(10)22/h10-12,14-16,22-24H,1,3-8H2,2H3/t10-,11-,12+,14+,15-,16-,17-,18+,19-,20-/m0/s1
SMILES:	C=C1[C@@H]2CC[C@H]3[C@]45CCC[C@@]6(C)CO[C@H]5O[C@@]([C@H]([C@@H]46)O)([C@@]3(C1=O)[C@@H]2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252120
PubChem CID:	44445775
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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	9000.0	nM	PMID[476989]
NPT1097	Cell Line	MKN-45	Homo sapiens	IC50	=	3900.0	nM	PMID[476989]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	4200.0	nM	PMID[476989]

☑ 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 NPC145625 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	295
0.1-0.2	2063
0.2-0.3	6186
0.3-0.4	10929
0.4-0.5	10289
0.5-0.6	6211
0.6-0.7	3788
0.7-0.8	2199
0.8-0.85	594
0.85-0.9	70
0.9-0.95	44
0.95-1	29

Similarity Score	Similarity Level	Natural Product ID
0.9808	High Similarity	NPC157929
0.9714	High Similarity	NPC94141
0.9712	High Similarity	NPC122339
0.9712	High Similarity	NPC63244
0.9623	High Similarity	NPC17165
0.9619	High Similarity	NPC473303
0.9619	High Similarity	NPC471245
0.9619	High Similarity	NPC471244
0.9615	High Similarity	NPC471476
0.9615	High Similarity	NPC473324
0.9533	High Similarity	NPC229752
0.9528	High Similarity	NPC471248
0.9515	High Similarity	NPC67745
0.9515	High Similarity	NPC471461
0.9444	High Similarity	NPC78836
0.9423	High Similarity	NPC189663
0.9423	High Similarity	NPC55973
0.9423	High Similarity	NPC89860
0.9352	High Similarity	NPC88945
0.9346	High Similarity	NPC132668
0.9333	High Similarity	NPC118721
0.9333	High Similarity	NPC252679
0.9333	High Similarity	NPC102741
0.9266	High Similarity	NPC473304
0.9245	High Similarity	NPC471093
0.9238	High Similarity	NPC469733
0.9238	High Similarity	NPC469729
0.9231	High Similarity	NPC307660
0.9231	High Similarity	NPC12823
0.9231	High Similarity	NPC130511
0.9159	High Similarity	NPC213320
0.9159	High Similarity	NPC29505
0.9151	High Similarity	NPC469744
0.9143	High Similarity	NPC469746
0.9074	High Similarity	NPC473397
0.9074	High Similarity	NPC472719
0.9074	High Similarity	NPC473352
0.9074	High Similarity	NPC207845
0.9074	High Similarity	NPC474927
0.9057	High Similarity	NPC473410
0.9057	High Similarity	NPC469984
0.9057	High Similarity	NPC471094
0.9057	High Similarity	NPC63841
0.9048	High Similarity	NPC56656
0.8991	High Similarity	NPC471252
0.8981	High Similarity	NPC329953
0.8981	High Similarity	NPC274833
0.8972	High Similarity	NPC131903
0.8962	High Similarity	NPC186054
0.8962	High Similarity	NPC471474
0.8942	High Similarity	NPC475803
0.8942	High Similarity	NPC309388
0.8889	High Similarity	NPC474786
0.8889	High Similarity	NPC85391
0.8889	High Similarity	NPC137104
0.8889	High Similarity	NPC320383
0.8868	High Similarity	NPC4115
0.8846	High Similarity	NPC14634
0.8829	High Similarity	NPC472718
0.8807	High Similarity	NPC471243
0.8796	High Similarity	NPC8431
0.8796	High Similarity	NPC274827
0.8774	High Similarity	NPC202793
0.8739	High Similarity	NPC243354
0.8704	High Similarity	NPC232133
0.8679	High Similarity	NPC107385
0.8679	High Similarity	NPC139347
0.8649	High Similarity	NPC73986
0.8649	High Similarity	NPC194273
0.8636	High Similarity	NPC11035
0.8636	High Similarity	NPC56025
0.8624	High Similarity	NPC469983
0.8598	High Similarity	NPC13149
0.8559	High Similarity	NPC470543
0.8532	High Similarity	NPC231278
0.8532	High Similarity	NPC218123
0.8532	High Similarity	NPC273155
0.8532	High Similarity	NPC112895
0.8505	High Similarity	NPC209298
0.8505	High Similarity	NPC277074
0.8491	Intermediate Similarity	NPC471790
0.8482	Intermediate Similarity	NPC146563
0.8482	Intermediate Similarity	NPC320118
0.8455	Intermediate Similarity	NPC240125
0.8455	Intermediate Similarity	NPC473844
0.8455	Intermediate Similarity	NPC51947
0.8455	Intermediate Similarity	NPC91583
0.844	Intermediate Similarity	NPC96333
0.844	Intermediate Similarity	NPC166993
0.844	Intermediate Similarity	NPC88833
0.8426	Intermediate Similarity	NPC474558
0.8421	Intermediate Similarity	NPC477252
0.8421	Intermediate Similarity	NPC156651
0.8421	Intermediate Similarity	NPC218970
0.8407	Intermediate Similarity	NPC54395
0.8396	Intermediate Similarity	NPC127408
0.8396	Intermediate Similarity	NPC470388
0.8396	Intermediate Similarity	NPC287676
0.8396	Intermediate Similarity	NPC291785
0.8393	Intermediate Similarity	NPC243572
0.8378	Intermediate Similarity	NPC98069
0.8378	Intermediate Similarity	NPC49730
0.8364	Intermediate Similarity	NPC88744
0.8349	Intermediate Similarity	NPC138908
0.8349	Intermediate Similarity	NPC164600
0.8349	Intermediate Similarity	NPC200957
0.8349	Intermediate Similarity	NPC103172
0.8348	Intermediate Similarity	NPC475632
0.8348	Intermediate Similarity	NPC86020
0.8333	Intermediate Similarity	NPC469823
0.8333	Intermediate Similarity	NPC469820
0.8333	Intermediate Similarity	NPC87927
0.8333	Intermediate Similarity	NPC122811
0.8333	Intermediate Similarity	NPC137414
0.8319	Intermediate Similarity	NPC273962
0.8319	Intermediate Similarity	NPC102619
0.8318	Intermediate Similarity	NPC289148
0.8318	Intermediate Similarity	NPC52899
0.8318	Intermediate Similarity	NPC163963
0.8304	Intermediate Similarity	NPC272242
0.8304	Intermediate Similarity	NPC240734
0.8304	Intermediate Similarity	NPC91838
0.8304	Intermediate Similarity	NPC275668
0.8304	Intermediate Similarity	NPC204392
0.8304	Intermediate Similarity	NPC1876
0.8302	Intermediate Similarity	NPC16911
0.8302	Intermediate Similarity	NPC78427
0.8291	Intermediate Similarity	NPC470478
0.8273	Intermediate Similarity	NPC470166
0.8273	Intermediate Similarity	NPC61071
0.8257	Intermediate Similarity	NPC470167
0.8257	Intermediate Similarity	NPC301787
0.8257	Intermediate Similarity	NPC101842
0.8252	Intermediate Similarity	NPC299185
0.8246	Intermediate Similarity	NPC102088
0.8246	Intermediate Similarity	NPC477580
0.8241	Intermediate Similarity	NPC148628
0.8241	Intermediate Similarity	NPC246736
0.8241	Intermediate Similarity	NPC286519
0.8241	Intermediate Similarity	NPC88203
0.8241	Intermediate Similarity	NPC304832
0.8241	Intermediate Similarity	NPC214946
0.8241	Intermediate Similarity	NPC76866
0.8235	Intermediate Similarity	NPC469841
0.8235	Intermediate Similarity	NPC248202
0.8235	Intermediate Similarity	NPC469842
0.823	Intermediate Similarity	NPC474265
0.823	Intermediate Similarity	NPC210420
0.823	Intermediate Similarity	NPC205534
0.822	Intermediate Similarity	NPC475431
0.8205	Intermediate Similarity	NPC108072
0.8205	Intermediate Similarity	NPC475187
0.8205	Intermediate Similarity	NPC281840
0.819	Intermediate Similarity	NPC470513
0.819	Intermediate Similarity	NPC470514
0.819	Intermediate Similarity	NPC239293
0.819	Intermediate Similarity	NPC469822
0.819	Intermediate Similarity	NPC231060
0.819	Intermediate Similarity	NPC41070
0.819	Intermediate Similarity	NPC84018
0.819	Intermediate Similarity	NPC138245
0.8182	Intermediate Similarity	NPC222833
0.8174	Intermediate Similarity	NPC473126
0.8173	Intermediate Similarity	NPC144739
0.8173	Intermediate Similarity	NPC181594
0.8167	Intermediate Similarity	NPC47113
0.8167	Intermediate Similarity	NPC174367
0.8165	Intermediate Similarity	NPC216114
0.8158	Intermediate Similarity	NPC238935
0.8158	Intermediate Similarity	NPC260665
0.8158	Intermediate Similarity	NPC293038
0.8158	Intermediate Similarity	NPC62696
0.8158	Intermediate Similarity	NPC475208
0.8155	Intermediate Similarity	NPC261994
0.8155	Intermediate Similarity	NPC149761
0.8155	Intermediate Similarity	NPC470378
0.8148	Intermediate Similarity	NPC252614
0.8148	Intermediate Similarity	NPC46848
0.8136	Intermediate Similarity	NPC475182
0.8131	Intermediate Similarity	NPC471038
0.8131	Intermediate Similarity	NPC474793
0.8125	Intermediate Similarity	NPC246205
0.812	Intermediate Similarity	NPC161738
0.812	Intermediate Similarity	NPC190939
0.812	Intermediate Similarity	NPC197003
0.8115	Intermediate Similarity	NPC476966
0.8113	Intermediate Similarity	NPC13949
0.8108	Intermediate Similarity	NPC287269
0.8103	Intermediate Similarity	NPC309433
0.8103	Intermediate Similarity	NPC300419
0.8103	Intermediate Similarity	NPC470171
0.8095	Intermediate Similarity	NPC302008
0.8095	Intermediate Similarity	NPC261333
0.8095	Intermediate Similarity	NPC191094
0.8095	Intermediate Similarity	NPC91772
0.8095	Intermediate Similarity	NPC101233
0.8095	Intermediate Similarity	NPC29247
0.8095	Intermediate Similarity	NPC153775
0.8095	Intermediate Similarity	NPC129004
0.8095	Intermediate Similarity	NPC111524

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 NPC145625 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	297
0.1-0.2	2410
0.2-0.3	4036
0.3-0.4	1529
0.4-0.5	444
0.5-0.6	259
0.6-0.7	137
0.7-0.8	35
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
0.8	Intermediate Similarity	NPD8133	Approved
0.8	Intermediate Similarity	NPD8328	Phase 3
0.7949	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7946	Intermediate Similarity	NPD6412	Phase 2
0.7807	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD6370	Approved
0.7768	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7736	Approved
0.768	Intermediate Similarity	NPD7319	Approved
0.7603	Intermediate Similarity	NPD6054	Approved
0.7581	Intermediate Similarity	NPD7507	Approved
0.7541	Intermediate Similarity	NPD6016	Approved
0.7541	Intermediate Similarity	NPD6015	Approved
0.748	Intermediate Similarity	NPD5988	Approved
0.7459	Intermediate Similarity	NPD6059	Approved
0.7398	Intermediate Similarity	NPD8033	Approved
0.7381	Intermediate Similarity	NPD8293	Discontinued
0.736	Intermediate Similarity	NPD7492	Approved
0.7317	Intermediate Similarity	NPD6319	Approved
0.7317	Intermediate Similarity	NPD8377	Approved
0.7317	Intermediate Similarity	NPD8294	Approved
0.7302	Intermediate Similarity	NPD6616	Approved
0.7265	Intermediate Similarity	NPD6686	Approved
0.7265	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD8296	Approved
0.7258	Intermediate Similarity	NPD8380	Approved
0.7258	Intermediate Similarity	NPD8379	Approved
0.7258	Intermediate Similarity	NPD8378	Approved
0.7258	Intermediate Similarity	NPD8335	Approved
0.7244	Intermediate Similarity	NPD7078	Approved
0.7236	Intermediate Similarity	NPD7516	Approved
0.7213	Intermediate Similarity	NPD6009	Approved
0.7154	Intermediate Similarity	NPD7328	Approved
0.7154	Intermediate Similarity	NPD7327	Approved
0.7143	Intermediate Similarity	NPD4634	Approved
0.7107	Intermediate Similarity	NPD4632	Approved
0.7091	Intermediate Similarity	NPD8034	Phase 2
0.7091	Intermediate Similarity	NPD8035	Phase 2
0.7073	Intermediate Similarity	NPD7115	Discovery
0.7027	Intermediate Similarity	NPD8171	Discontinued
0.7025	Intermediate Similarity	NPD6882	Approved
0.6984	Remote Similarity	NPD8513	Phase 3
0.6984	Remote Similarity	NPD7503	Approved
0.6984	Remote Similarity	NPD8517	Approved
0.6984	Remote Similarity	NPD8515	Approved
0.6984	Remote Similarity	NPD8516	Approved
0.6923	Remote Similarity	NPD6033	Approved
0.6891	Remote Similarity	NPD5697	Approved
0.6885	Remote Similarity	NPD8297	Approved
0.6875	Remote Similarity	NPD6067	Discontinued
0.6852	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6881	Approved
0.6833	Remote Similarity	NPD6899	Approved
0.681	Remote Similarity	NPD5286	Approved
0.681	Remote Similarity	NPD5285	Approved
0.681	Remote Similarity	NPD4696	Approved
0.6807	Remote Similarity	NPD6008	Approved
0.6807	Remote Similarity	NPD6402	Approved
0.6807	Remote Similarity	NPD5739	Approved
0.6807	Remote Similarity	NPD6675	Approved
0.6807	Remote Similarity	NPD7128	Approved
0.6803	Remote Similarity	NPD6649	Approved
0.6803	Remote Similarity	NPD6650	Approved
0.6783	Remote Similarity	NPD7902	Approved
0.6783	Remote Similarity	NPD4755	Approved
0.6777	Remote Similarity	NPD6013	Approved
0.6777	Remote Similarity	NPD6373	Approved
0.6777	Remote Similarity	NPD6014	Approved
0.6777	Remote Similarity	NPD6012	Approved
0.6777	Remote Similarity	NPD6372	Approved
0.675	Remote Similarity	NPD5701	Approved
0.6726	Remote Similarity	NPD6399	Phase 3
0.6724	Remote Similarity	NPD4225	Approved
0.6721	Remote Similarity	NPD7290	Approved
0.6721	Remote Similarity	NPD6883	Approved
0.6721	Remote Similarity	NPD7102	Approved
0.6719	Remote Similarity	NPD5983	Phase 2
0.6695	Remote Similarity	NPD5211	Phase 2
0.6695	Remote Similarity	NPD5225	Approved
0.6695	Remote Similarity	NPD5226	Approved
0.6695	Remote Similarity	NPD4633	Approved
0.6695	Remote Similarity	NPD5224	Approved
0.6694	Remote Similarity	NPD7320	Approved
0.6694	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6639	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5174	Approved
0.6639	Remote Similarity	NPD5175	Approved
0.6637	Remote Similarity	NPD7515	Phase 2
0.6637	Remote Similarity	NPD6079	Approved
0.6636	Remote Similarity	NPD3618	Phase 1
0.6615	Remote Similarity	NPD7604	Phase 2
0.661	Remote Similarity	NPD5223	Approved
0.6607	Remote Similarity	NPD5328	Approved
0.6589	Remote Similarity	NPD6921	Approved
0.6583	Remote Similarity	NPD5141	Approved
0.6581	Remote Similarity	NPD7638	Approved
0.6579	Remote Similarity	NPD4202	Approved
0.6567	Remote Similarity	NPD5956	Approved
0.6552	Remote Similarity	NPD5222	Approved
0.6552	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4697	Phase 3
0.6552	Remote Similarity	NPD5221	Approved
0.6525	Remote Similarity	NPD7640	Approved
0.6525	Remote Similarity	NPD7639	Approved
0.6522	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7900	Approved
0.6515	Remote Similarity	NPD6336	Discontinued
0.6496	Remote Similarity	NPD5173	Approved
0.6486	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6274	Approved
0.6457	Remote Similarity	NPD6940	Discontinued
0.6455	Remote Similarity	NPD4786	Approved
0.6452	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD4729	Approved
0.6423	Remote Similarity	NPD5128	Approved
0.6423	Remote Similarity	NPD4730	Approved
0.6422	Remote Similarity	NPD3667	Approved
0.64	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD4767	Approved
0.6393	Remote Similarity	NPD4768	Approved
0.6389	Remote Similarity	NPD6928	Phase 2
0.6381	Remote Similarity	NPD3703	Phase 2
0.6364	Remote Similarity	NPD4754	Approved
0.6356	Remote Similarity	NPD6083	Phase 2
0.6356	Remote Similarity	NPD6084	Phase 2
0.6355	Remote Similarity	NPD6114	Approved
0.6355	Remote Similarity	NPD6118	Approved
0.6355	Remote Similarity	NPD6697	Approved
0.6355	Remote Similarity	NPD6115	Approved
0.633	Remote Similarity	NPD1780	Approved
0.633	Remote Similarity	NPD1779	Approved
0.6325	Remote Similarity	NPD5210	Approved
0.6325	Remote Similarity	NPD4629	Approved
0.632	Remote Similarity	NPD5248	Approved
0.632	Remote Similarity	NPD5251	Approved
0.632	Remote Similarity	NPD5247	Approved
0.632	Remote Similarity	NPD5249	Phase 3
0.632	Remote Similarity	NPD5250	Approved
0.632	Remote Similarity	NPD6371	Approved
0.6316	Remote Similarity	NPD4753	Phase 2
0.6308	Remote Similarity	NPD7100	Approved
0.6308	Remote Similarity	NPD7101	Approved
0.6306	Remote Similarity	NPD3133	Approved
0.6306	Remote Similarity	NPD3665	Phase 1
0.6306	Remote Similarity	NPD3666	Approved
0.6303	Remote Similarity	NPD5696	Approved
0.6279	Remote Similarity	NPD6317	Approved
0.627	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.627	Remote Similarity	NPD5217	Approved
0.627	Remote Similarity	NPD5215	Approved
0.627	Remote Similarity	NPD5216	Approved
0.6262	Remote Similarity	NPD6116	Phase 1
0.6239	Remote Similarity	NPD5282	Discontinued
0.6231	Remote Similarity	NPD6313	Approved
0.6231	Remote Similarity	NPD6314	Approved
0.6231	Remote Similarity	NPD6335	Approved
0.6228	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD8074	Phase 3
0.6216	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD3669	Approved
0.6212	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.621	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6411	Approved
0.6198	Remote Similarity	NPD1700	Approved
0.619	Remote Similarity	NPD5169	Approved
0.619	Remote Similarity	NPD5135	Approved
0.619	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5695	Phase 3
0.6183	Remote Similarity	NPD4522	Approved
0.6176	Remote Similarity	NPD8336	Approved
0.6176	Remote Similarity	NPD8337	Approved
0.6168	Remote Similarity	NPD6117	Approved
0.6148	Remote Similarity	NPD7632	Discontinued
0.6142	Remote Similarity	NPD5127	Approved
0.614	Remote Similarity	NPD3573	Approved
0.6122	Remote Similarity	NPD7625	Phase 1
0.6115	Remote Similarity	NPD8338	Approved
0.6115	Remote Similarity	NPD8449	Approved
0.6095	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD7525	Registered
0.609	Remote Similarity	NPD6908	Approved
0.609	Remote Similarity	NPD6909	Approved
0.6077	Remote Similarity	NPD6868	Approved
0.6071	Remote Similarity	NPD8450	Suspended
0.6058	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD7146	Approved
0.6053	Remote Similarity	NPD6409	Approved
0.6053	Remote Similarity	NPD5330	Approved
0.6053	Remote Similarity	NPD7334	Approved
0.6053	Remote Similarity	NPD6684	Approved
0.6053	Remote Similarity	NPD7521	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