NPASS Compound

Structure

NPC475195 OpenBabel07101719122D 44 47 0 0 1 0 0 0 0 0999 V2000 5.7488 -1.2549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0496 0.4508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6924 -4.3642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4676 0.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8053 -3.7267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8769 -6.0248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8401 -0.2736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8420 -2.8057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3420 -1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3420 -3.6717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3420 -1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3420 -3.6717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4936 -1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8508 -0.6736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4220 -0.1416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8204 -3.5530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4068 -0.3152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4524 0.2057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4480 -2.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8921 -5.8512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8420 -2.8057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4936 -2.4397 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4784 -2.6133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7792 -0.9076 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8508 -3.2057 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.8794 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1212 -1.8473 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3420 -1.9397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8420 -2.8057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1929 -4.1454 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0952 0.9718 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4329 -3.1343 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2493 -6.6172 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7660 -3.5222 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3420 -3.6717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1777 -4.3191 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7944 -0.7340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1060 -2.0209 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5501 -4.9115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3420 -1.9397 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 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 2 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 22 2 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 14 33 1 0 0 0 0 15 17 2 0 0 0 0 16 24 2 0 0 0 0 16 39 1 0 0 0 0 18 27 1 0 0 0 0 19 34 2 0 0 0 0 19 40 1 0 0 0 0 20 35 2 0 0 0 0 20 41 1 0 0 0 0 21 36 2 0 0 0 0 21 42 1 0 0 0 0 22 31 1 0 0 0 0 23 13 1 6 0 0 0 23 24 1 0 0 0 0 23 26 1 0 0 0 0 24 28 1 0 0 0 0 25 15 1 6 0 0 0 25 28 1 0 0 0 0 25 40 1 0 0 0 0 26 18 1 1 0 0 0 26 32 1 0 0 0 0 27 29 1 0 0 0 0 27 37 1 6 0 0 0 28 41 1 1 0 0 0 29 30 1 0 0 0 0 29 43 1 6 0 0 0 30 33 1 6 0 0 0 30 44 1 0 0 0 0 31 38 2 0 0 0 0 31 43 1 0 0 0 0 32 39 1 0 0 0 0 32 42 1 1 0 0 0 33 7 1 6 0 0 0 33 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	612.26
Volume:	615.426
LogP:	3.212
LogD:	2.285
LogS:	-3.868
# Rotatable Bonds:	12
TPSA:	147.19
# H-Bond Aceptor:	11
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.197
Synthetic Accessibility Score:	5.662
Fsp3:	0.515
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.144
MDCK Permeability:	0.00010282281436957419
Pgp-inhibitor:	0.985
Pgp-substrate:	0.179
Human Intestinal Absorption (HIA):	0.542
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.211
Plasma Protein Binding (PPB):	66.21778869628906%
Volume Distribution (VD):	2.336
Pgp-substrate:	17.358463287353516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.03
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.822
CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.499
CYP3A4-substrate:	0.315

ADMET: Excretion

Clearance (CL):	3.726
Half-life (T1/2):	0.126

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.974
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.956
Rat Oral Acute Toxicity:	0.769
Maximum Recommended Daily Dose:	0.092
Skin Sensitization:	0.139
Carcinogencity:	0.65
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC475195

Natural Product ID:	NPC475195
*Common Name:**	Florxenilide B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WHFYKRNZGHQAED-AYKORBDZSA-N
Standard InCHI:	InChI=1S/C33H40O11/c1-17(2)15-25(40-19(4)34)28(41-20(5)35)24-16-39-32(42-21(6)36)26-18(3)27(37)29(30-33(7,44-30)14-13-23(24)26)43-31(38)22-11-9-8-10-12-22/h8-12,15-16,23,25-30,32,37H,3,13-14H2,1-2,4-7H3/t23-,25-,26+,27+,28+,29+,30+,32+,33+/m1/s1
SMILES:	CC(=CC(C(C1=COC(C2C1CCC3(C(O3)C(C(C2=C)O)OC(=O)C4=CC=CC=C4)C)OC(=O)C)OC(=O)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500720
PubChem CID:	11520070
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids and derivatives

*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
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16643051]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9868153]
NPO5870	Xenia florida	Species	n.a.	n.a.	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
ED50	3
IC50	1

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	11.4	ug ml-1	PMID[506326]
NPT1183	Cell Line	WiDr	Homo sapiens	ED50	=	1.88	ug ml-1	PMID[506326]
NPT1183	Cell Line	WiDr	Homo sapiens	IC50	=	3700.0	nM	PMID[506326]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	8.03	ug ml-1	PMID[506326]

☑ 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 NPC475195 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	306
0.1-0.2	1075
0.2-0.3	2540
0.3-0.4	6646
0.4-0.5	10781
0.5-0.6	11357
0.6-0.7	8991
0.7-0.8	984
0.8-0.85	13
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9542	High Similarity	NPC136608
0.9542	High Similarity	NPC38420
0.8881	High Similarity	NPC475478
0.8676	High Similarity	NPC475569
0.85	High Similarity	NPC27721
0.8429	Intermediate Similarity	NPC202729
0.8417	Intermediate Similarity	NPC28836
0.8382	Intermediate Similarity	NPC148026
0.8345	Intermediate Similarity	NPC472248
0.8333	Intermediate Similarity	NPC319995
0.8333	Intermediate Similarity	NPC289415
0.8333	Intermediate Similarity	NPC17567
0.8322	Intermediate Similarity	NPC158546
0.8322	Intermediate Similarity	NPC289021
0.8321	Intermediate Similarity	NPC301857
0.831	Intermediate Similarity	NPC473301
0.8309	Intermediate Similarity	NPC114096
0.8286	Intermediate Similarity	NPC311492
0.8286	Intermediate Similarity	NPC470143
0.8286	Intermediate Similarity	NPC322503
0.8273	Intermediate Similarity	NPC233692
0.8273	Intermediate Similarity	NPC233860
0.8273	Intermediate Similarity	NPC239358
0.8243	Intermediate Similarity	NPC189631
0.8227	Intermediate Similarity	NPC200154
0.8219	Intermediate Similarity	NPC296659
0.8219	Intermediate Similarity	NPC202391
0.82	Intermediate Similarity	NPC472658
0.82	Intermediate Similarity	NPC472657
0.8162	Intermediate Similarity	NPC57607
0.8151	Intermediate Similarity	NPC186296
0.8146	Intermediate Similarity	NPC194705
0.8138	Intermediate Similarity	NPC192658
0.8129	Intermediate Similarity	NPC27712
0.8125	Intermediate Similarity	NPC162613
0.8125	Intermediate Similarity	NPC87934
0.8121	Intermediate Similarity	NPC469448
0.8117	Intermediate Similarity	NPC329997
0.8112	Intermediate Similarity	NPC471345
0.8095	Intermediate Similarity	NPC77922
0.8095	Intermediate Similarity	NPC473281
0.8092	Intermediate Similarity	NPC229354
0.8088	Intermediate Similarity	NPC138798
0.8082	Intermediate Similarity	NPC477894
0.8082	Intermediate Similarity	NPC284957
0.8079	Intermediate Similarity	NPC474620
0.8069	Intermediate Similarity	NPC242355
0.8067	Intermediate Similarity	NPC478236
0.8067	Intermediate Similarity	NPC469415
0.8067	Intermediate Similarity	NPC478234
0.8056	Intermediate Similarity	NPC9905
0.8054	Intermediate Similarity	NPC473149
0.8042	Intermediate Similarity	NPC472374
0.8042	Intermediate Similarity	NPC472372
0.8039	Intermediate Similarity	NPC478232
0.8029	Intermediate Similarity	NPC246166
0.8028	Intermediate Similarity	NPC114116
0.8027	Intermediate Similarity	NPC34943
0.8027	Intermediate Similarity	NPC242756
0.8027	Intermediate Similarity	NPC478250
0.8015	Intermediate Similarity	NPC141970
0.8015	Intermediate Similarity	NPC140561
0.8014	Intermediate Similarity	NPC154262
0.8014	Intermediate Similarity	NPC137501
0.8014	Intermediate Similarity	NPC34012
0.8014	Intermediate Similarity	NPC159387
0.8014	Intermediate Similarity	NPC7518
0.8013	Intermediate Similarity	NPC240592
0.8013	Intermediate Similarity	NPC117346
0.8	Intermediate Similarity	NPC472547
0.8	Intermediate Similarity	NPC222102
0.8	Intermediate Similarity	NPC303429
0.7987	Intermediate Similarity	NPC143246
0.7987	Intermediate Similarity	NPC474268
0.7987	Intermediate Similarity	NPC473147
0.7987	Intermediate Similarity	NPC475539
0.7987	Intermediate Similarity	NPC119773
0.7975	Intermediate Similarity	NPC109990
0.7974	Intermediate Similarity	NPC475548
0.7974	Intermediate Similarity	NPC290683
0.7974	Intermediate Similarity	NPC475638
0.7973	Intermediate Similarity	NPC184464
0.7973	Intermediate Similarity	NPC472556
0.7973	Intermediate Similarity	NPC134131
0.7973	Intermediate Similarity	NPC251062
0.7973	Intermediate Similarity	NPC25043
0.7972	Intermediate Similarity	NPC473399
0.7972	Intermediate Similarity	NPC169398
0.7972	Intermediate Similarity	NPC473216
0.7959	Intermediate Similarity	NPC91703
0.7959	Intermediate Similarity	NPC95449
0.7947	Intermediate Similarity	NPC96599
0.7945	Intermediate Similarity	NPC77493
0.7945	Intermediate Similarity	NPC291599
0.7945	Intermediate Similarity	NPC41481
0.7945	Intermediate Similarity	NPC97947
0.7945	Intermediate Similarity	NPC87448
0.7945	Intermediate Similarity	NPC27377
0.7945	Intermediate Similarity	NPC472576
0.7945	Intermediate Similarity	NPC118080
0.7945	Intermediate Similarity	NPC16912
0.7919	Intermediate Similarity	NPC240115
0.7919	Intermediate Similarity	NPC475528
0.7919	Intermediate Similarity	NPC20255
0.7919	Intermediate Similarity	NPC312393
0.7914	Intermediate Similarity	NPC10121
0.7914	Intermediate Similarity	NPC92283
0.7914	Intermediate Similarity	NPC10883
0.7914	Intermediate Similarity	NPC124878
0.7914	Intermediate Similarity	NPC204214
0.7914	Intermediate Similarity	NPC35338
0.7914	Intermediate Similarity	NPC63404
0.7914	Intermediate Similarity	NPC198918
0.7914	Intermediate Similarity	NPC231888
0.7914	Intermediate Similarity	NPC290276
0.7911	Intermediate Similarity	NPC145847
0.7908	Intermediate Similarity	NPC469398
0.7908	Intermediate Similarity	NPC469422
0.7908	Intermediate Similarity	NPC469456
0.7908	Intermediate Similarity	NPC478235
0.7908	Intermediate Similarity	NPC34066
0.7905	Intermediate Similarity	NPC38696
0.7899	Intermediate Similarity	NPC244454
0.7899	Intermediate Similarity	NPC162925
0.7899	Intermediate Similarity	NPC87153
0.7895	Intermediate Similarity	NPC35097
0.7885	Intermediate Similarity	NPC187205
0.7881	Intermediate Similarity	NPC477099
0.7881	Intermediate Similarity	NPC25484
0.7881	Intermediate Similarity	NPC232583
0.7881	Intermediate Similarity	NPC477101
0.7881	Intermediate Similarity	NPC477097
0.7877	Intermediate Similarity	NPC275592
0.7877	Intermediate Similarity	NPC100913
0.7877	Intermediate Similarity	NPC90614
0.7877	Intermediate Similarity	NPC97667
0.7877	Intermediate Similarity	NPC171207
0.7872	Intermediate Similarity	NPC11025
0.7872	Intermediate Similarity	NPC475508
0.7871	Intermediate Similarity	NPC476784
0.7868	Intermediate Similarity	NPC229600
0.7867	Intermediate Similarity	NPC212808
0.7862	Intermediate Similarity	NPC39549
0.7857	Intermediate Similarity	NPC175333
0.7857	Intermediate Similarity	NPC257847
0.7852	Intermediate Similarity	NPC70403
0.7852	Intermediate Similarity	NPC472568
0.7852	Intermediate Similarity	NPC158663
0.7852	Intermediate Similarity	NPC171525
0.7852	Intermediate Similarity	NPC469349
0.7852	Intermediate Similarity	NPC470159
0.7852	Intermediate Similarity	NPC63304
0.7852	Intermediate Similarity	NPC471104
0.7852	Intermediate Similarity	NPC96903
0.7852	Intermediate Similarity	NPC92867
0.7852	Intermediate Similarity	NPC472575
0.7852	Intermediate Similarity	NPC125882
0.7852	Intermediate Similarity	NPC29704
0.7852	Intermediate Similarity	NPC471028
0.7852	Intermediate Similarity	NPC200471
0.7852	Intermediate Similarity	NPC177940
0.7852	Intermediate Similarity	NPC472572
0.7852	Intermediate Similarity	NPC470157
0.7852	Intermediate Similarity	NPC174982
0.7852	Intermediate Similarity	NPC311825
0.7852	Intermediate Similarity	NPC472571
0.7852	Intermediate Similarity	NPC184817
0.7852	Intermediate Similarity	NPC194938
0.7852	Intermediate Similarity	NPC473088
0.7852	Intermediate Similarity	NPC476973
0.7847	Intermediate Similarity	NPC477896
0.7847	Intermediate Similarity	NPC477893
0.7843	Intermediate Similarity	NPC477100
0.7843	Intermediate Similarity	NPC475379
0.7843	Intermediate Similarity	NPC471135
0.7843	Intermediate Similarity	NPC133430
0.7843	Intermediate Similarity	NPC477098
0.7843	Intermediate Similarity	NPC469477
0.7842	Intermediate Similarity	NPC77651
0.7842	Intermediate Similarity	NPC28069
0.7838	Intermediate Similarity	NPC31081
0.7838	Intermediate Similarity	NPC65833
0.7838	Intermediate Similarity	NPC245219
0.7829	Intermediate Similarity	NPC161955
0.7826	Intermediate Similarity	NPC471466
0.7823	Intermediate Similarity	NPC475413
0.7823	Intermediate Similarity	NPC474303
0.7823	Intermediate Similarity	NPC266374
0.7821	Intermediate Similarity	NPC323356
0.7821	Intermediate Similarity	NPC471138
0.7821	Intermediate Similarity	NPC477623
0.7821	Intermediate Similarity	NPC326328
0.7821	Intermediate Similarity	NPC475378
0.7821	Intermediate Similarity	NPC309991
0.781	Intermediate Similarity	NPC475328
0.7808	Intermediate Similarity	NPC65262
0.7808	Intermediate Similarity	NPC101686
0.7808	Intermediate Similarity	NPC469364
0.7806	Intermediate Similarity	NPC472127
0.7806	Intermediate Similarity	NPC469417

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 NPC475195 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	773
0.2-0.3	1678
0.3-0.4	2845
0.4-0.5	2247
0.5-0.6	1034
0.6-0.7	306
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
0.7832	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7685	Pre-registration
0.7516	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4628	Phase 3
0.7353	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7799	Discontinued
0.7285	Intermediate Similarity	NPD7266	Discontinued
0.725	Intermediate Similarity	NPD8455	Phase 2
0.7235	Intermediate Similarity	NPD8313	Approved
0.7235	Intermediate Similarity	NPD8312	Approved
0.7226	Intermediate Similarity	NPD2629	Approved
0.7185	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD2182	Approved
0.7143	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD969	Suspended
0.7045	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD5125	Phase 3
0.7042	Intermediate Similarity	NPD5126	Approved
0.7021	Intermediate Similarity	NPD9545	Approved
0.7018	Intermediate Similarity	NPD8368	Discontinued
0.7	Intermediate Similarity	NPD7458	Discontinued
0.6992	Remote Similarity	NPD5909	Discontinued
0.6985	Remote Similarity	NPD2067	Discontinued
0.6982	Remote Similarity	NPD3818	Discontinued
0.6981	Remote Similarity	NPD5403	Approved
0.698	Remote Similarity	NPD3764	Approved
0.6957	Remote Similarity	NPD4380	Phase 2
0.6943	Remote Similarity	NPD7236	Approved
0.6941	Remote Similarity	NPD7054	Approved
0.6919	Remote Similarity	NPD6559	Discontinued
0.6917	Remote Similarity	NPD6647	Phase 2
0.6912	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7075	Discontinued
0.6901	Remote Similarity	NPD7074	Phase 3
0.6901	Remote Similarity	NPD7472	Approved
0.6899	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8407	Phase 2
0.689	Remote Similarity	NPD5402	Approved
0.6879	Remote Similarity	NPD7808	Phase 3
0.6879	Remote Similarity	NPD6190	Approved
0.6871	Remote Similarity	NPD37	Approved
0.6871	Remote Similarity	NPD6801	Discontinued
0.6866	Remote Similarity	NPD164	Approved
0.6857	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5401	Approved
0.6848	Remote Similarity	NPD4967	Phase 2
0.6848	Remote Similarity	NPD4965	Approved
0.6848	Remote Similarity	NPD4966	Approved
0.6842	Remote Similarity	NPD6355	Discontinued
0.6842	Remote Similarity	NPD230	Phase 1
0.6839	Remote Similarity	NPD6004	Phase 3
0.6839	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6005	Phase 3
0.6839	Remote Similarity	NPD6002	Phase 3
0.6839	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7239	Suspended
0.6829	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1091	Approved
0.6828	Remote Similarity	NPD4807	Approved
0.6828	Remote Similarity	NPD4806	Approved
0.6824	Remote Similarity	NPD2798	Approved
0.6821	Remote Similarity	NPD7251	Discontinued
0.6818	Remote Similarity	NPD8434	Phase 2
0.6818	Remote Similarity	NPD1238	Approved
0.6818	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2575	Approved
0.6812	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4198	Discontinued
0.6806	Remote Similarity	NPD5306	Approved
0.6806	Remote Similarity	NPD5305	Approved
0.68	Remote Similarity	NPD7008	Discontinued
0.6797	Remote Similarity	NPD6653	Approved
0.6784	Remote Similarity	NPD7228	Approved
0.6783	Remote Similarity	NPD7741	Discontinued
0.6782	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6234	Discontinued
0.6765	Remote Similarity	NPD6685	Approved
0.6763	Remote Similarity	NPD6797	Phase 2
0.6763	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2797	Approved
0.6752	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD8360	Approved
0.6742	Remote Similarity	NPD9495	Approved
0.6742	Remote Similarity	NPD8361	Approved
0.6741	Remote Similarity	NPD1237	Approved
0.6733	Remote Similarity	NPD6832	Phase 2
0.6728	Remote Similarity	NPD1653	Approved
0.6727	Remote Similarity	NPD7819	Suspended
0.6723	Remote Similarity	NPD8150	Discontinued
0.671	Remote Similarity	NPD7033	Discontinued
0.671	Remote Similarity	NPD4308	Phase 3
0.6709	Remote Similarity	NPD3750	Approved
0.6709	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD5048	Discontinued
0.6688	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6799	Approved
0.6684	Remote Similarity	NPD7999	Approved
0.6667	Remote Similarity	NPD1930	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD1929	Approved
0.6648	Remote Similarity	NPD8435	Approved
0.6648	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7768	Phase 2
0.6646	Remote Similarity	NPD6599	Discontinued
0.6645	Remote Similarity	NPD7097	Phase 1
0.6645	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3268	Approved
0.6645	Remote Similarity	NPD2313	Discontinued
0.6644	Remote Similarity	NPD4135	Approved
0.6644	Remote Similarity	NPD4106	Approved
0.6644	Remote Similarity	NPD4136	Approved
0.6643	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD9493	Approved
0.6631	Remote Similarity	NPD8320	Phase 1
0.6631	Remote Similarity	NPD8319	Approved
0.6624	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.662	Remote Similarity	NPD5951	Approved
0.6604	Remote Similarity	NPD8166	Discontinued
0.6603	Remote Similarity	NPD2799	Discontinued
0.6601	Remote Similarity	NPD6233	Phase 2
0.66	Remote Similarity	NPD6085	Phase 2
0.66	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5647	Approved
0.6599	Remote Similarity	NPD6287	Discontinued
0.6588	Remote Similarity	NPD8127	Discontinued
0.6588	Remote Similarity	NPD7199	Phase 2
0.6587	Remote Similarity	NPD3817	Phase 2
0.6587	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.658	Remote Similarity	NPD7930	Approved
0.6578	Remote Similarity	NPD7435	Discontinued
0.6576	Remote Similarity	NPD7699	Phase 2
0.6576	Remote Similarity	NPD7700	Phase 2
0.6575	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD2066	Phase 3
0.6561	Remote Similarity	NPD1551	Phase 2
0.6554	Remote Similarity	NPD6637	Approved
0.6554	Remote Similarity	NPD9717	Approved
0.6552	Remote Similarity	NPD5844	Phase 1
0.6544	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD5765	Approved
0.6543	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD6798	Discontinued
0.6536	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD7240	Approved
0.6525	Remote Similarity	NPD6912	Phase 3
0.6516	Remote Similarity	NPD1933	Approved
0.6516	Remote Similarity	NPD5124	Phase 1
0.6516	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD447	Suspended
0.6507	Remote Similarity	NPD4102	Approved
0.6507	Remote Similarity	NPD4105	Approved
0.6506	Remote Similarity	NPD7411	Suspended
0.6505	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD6273	Approved
0.6503	Remote Similarity	NPD6534	Approved
0.6503	Remote Similarity	NPD6535	Approved
0.6497	Remote Similarity	NPD3748	Approved
0.6497	Remote Similarity	NPD1510	Phase 2
0.6494	Remote Similarity	NPD3751	Discontinued
0.6493	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD3226	Approved
0.6477	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6686	Approved
0.6474	Remote Similarity	NPD7583	Approved
0.6467	Remote Similarity	NPD1934	Approved
0.6463	Remote Similarity	NPD17	Approved
0.6462	Remote Similarity	NPD7838	Discovery
0.6462	Remote Similarity	NPD9256	Approved
0.6462	Remote Similarity	NPD9258	Approved
0.646	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7874	Approved
0.6458	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD2438	Suspended
0.6456	Remote Similarity	NPD2796	Approved
0.6452	Remote Similarity	NPD4307	Phase 2
0.645	Remote Similarity	NPD7058	Phase 2
0.645	Remote Similarity	NPD7057	Phase 3
0.6447	Remote Similarity	NPD5204	Approved
0.6447	Remote Similarity	NPD3663	Approved
0.6447	Remote Similarity	NPD3661	Approved
0.6447	Remote Similarity	NPD3664	Approved
0.6447	Remote Similarity	NPD3662	Phase 3
0.6444	Remote Similarity	NPD7798	Approved
0.6442	Remote Similarity	NPD2532	Approved
0.6442	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD2534	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