NPASS Compound

Structure

NPC295287 OpenBabel07101718232D 39 40 0 0 1 0 0 0 0 0999 V2000 3.9395 -0.0289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5229 -0.8940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4048 -3.4048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8037 -4.2207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5735 -4.7782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8500 -1.0266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3508 -2.2149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 -1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6977 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2330 -1.0505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2149 -3.0485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4828 -0.6492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0485 -0.4828 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5352 -1.0505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6977 -2.6977 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6473 -3.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2149 0.3508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3489 -1.1492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4828 0.3508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4828 -3.0485 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2330 -1.6473 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0485 -2.2149 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2149 -0.6492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3489 0.8508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0505 -3.2330 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3508 -0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6712 -4.8500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3489 -2.1492 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.6047 -4.4916 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9395 -2.6689 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0809 -1.1492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3489 1.8508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2418 -0.0289 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5147 -5.8377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0289 -3.9395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2207 -1.8037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8940 -4.2207 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 15 1 0 0 0 0 4 17 1 0 0 0 0 5 37 1 0 0 0 0 6 38 1 0 0 0 0 7 8 1 0 0 0 0 7 9 2 0 0 0 0 8 15 2 0 0 0 0 9 21 1 0 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 12 17 2 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 1 1 1 0 0 0 15 27 1 0 0 0 0 16 3 1 1 0 0 0 16 23 1 0 0 0 0 17 26 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 19 24 1 0 0 0 0 19 29 1 0 0 0 0 20 25 2 0 0 0 0 20 31 1 0 0 0 0 21 26 1 0 0 0 0 21 37 1 1 0 0 0 22 23 1 0 0 0 0 22 38 1 6 0 0 0 23 32 1 6 0 0 0 24 33 1 0 0 0 0 25 34 1 0 0 0 0 26 39 1 6 0 0 0 27 31 2 3 0 0 0 27 35 1 0 0 0 0 28 30 2 0 0 0 0 28 36 1 0 0 0 0 28 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	566.24
Volume:	562.166
LogP:	3.59
LogD:	2.618
LogS:	-3.716
# Rotatable Bonds:	4
TPSA:	160.57
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.204
Synthetic Accessibility Score:	6.1
Fsp3:	0.5
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:	-4.863
MDCK Permeability:	9.994434549298603e-06
Pgp-inhibitor:	0.745
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.675
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	99.64629364013672%
Volume Distribution (VD):	0.544
Pgp-substrate:	1.8452070951461792%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.458
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.167
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.214
CYP3A4-substrate:	0.241

ADMET: Excretion

Clearance (CL):	8.458
Half-life (T1/2):	0.084

ADMET: Toxicity

hERG Blockers:	0.179
Human Hepatotoxicity (H-HT):	0.986
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.378
Rat Oral Acute Toxicity:	0.963
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.901
Carcinogencity:	0.201
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC295287

Natural Product ID:	NPC295287
*Common Name:**	[(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-20-Chloro-6,21,22-Trihydroxy-5,11-Dimethoxy-3,7,9,15-Tetramethyl-16-Oxo-17-Azabicyclo[16.3.1]Docosa-1(22),8,12,14,18,20-Hexaen-10-Yl] Carbamate
IUPAC Name:	[(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-20-chloro-6,21,22-trihydroxy-5,11-dimethoxy-3,7,9,15-tetramethyl-16-oxo-17-azabicyclo[16.3.1]docosa-1(22),8,12,14,18,20-hexaen-10-yl] carbamate
Synonyms:
Standard InCHIKey:	ZXJVPFOYHLXWJE-LVBRMASUSA-N
Standard InCHI:	InChI=1S/C28H39ClN2O8/c1-14-10-18-24(33)19(29)13-20(25(18)34)31-27(35)15(2)8-7-9-21(37-5)26(39-28(30)36)17(4)12-16(3)23(32)22(11-14)38-6/h7-9,12-14,16,21-23,26,32-34H,10-11H2,1-6H3,(H2,30,36)(H,31,35)/b9-7-,15-8+,17-12+/t14-,16+,21+,22+,23-,26+/m1/s1
SMILES:	C[C@@H]1Cc2c(c(cc(c2O)N=C(/C(=C/C=C[C@@H]([C@H](/C(=C/[C@H](C)[C@H]([C@H](C1)OC)O)/C)OC(=N)O)OC)/C)O)Cl)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517853
PubChem CID:	24992054
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000064] Macrolactams

*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
NPO13391	Streptomyces hygroscopicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14563159]
NPO13391	Streptomyces hygroscopicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15844961]
NPO13391	Streptomyces hygroscopicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16378365]
NPO13391	Streptomyces hygroscopicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16453790]
NPO13391	Streptomyces hygroscopicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16724461]
NPO13391	Streptomyces hygroscopicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17632514]
NPO13391	Streptomyces hygroscopicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19231864]
NPO13391	Streptomyces hygroscopicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21486005]
NPO13391	Streptomyces hygroscopicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21504214]
NPO13391	Streptomyces hygroscopicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24224794]
NPO13391	Streptomyces hygroscopicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3170341]
NPO13391	Streptomyces hygroscopicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3819734]
NPO13391	Streptomyces hygroscopicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[5549382]
NPO13391	Streptomyces hygroscopicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[TCMID]
NPO13391	Streptomyces hygroscopicus	Species	Streptomycetaceae	Bacteria	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	6

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	394.0	nM	PMID[484962]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	350.0	nM	PMID[484962]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	422.0	nM	PMID[484962]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	330.0	nM	PMID[484962]
NPT2335	Cell Line	NCI-H596		IC50	=	710.0	nM	PMID[484962]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	443.0	nM	PMID[484962]

☑ 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 NPC295287 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	340
0.1-0.2	1913
0.2-0.3	10636
0.3-0.4	8674
0.4-0.5	17357
0.5-0.6	3668
0.6-0.7	100
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9042	High Similarity	NPC238430
0.779	Intermediate Similarity	NPC225381
0.75	Intermediate Similarity	NPC72291
0.7258	Intermediate Similarity	NPC310894
0.7186	Intermediate Similarity	NPC101372
0.7081	Intermediate Similarity	NPC292143
0.7081	Intermediate Similarity	NPC139506
0.7	Intermediate Similarity	NPC95412
0.6984	Remote Similarity	NPC83241
0.6862	Remote Similarity	NPC204179
0.6836	Remote Similarity	NPC314113
0.6802	Remote Similarity	NPC477391
0.6763	Remote Similarity	NPC313466
0.6751	Remote Similarity	NPC315934
0.6751	Remote Similarity	NPC477392
0.6734	Remote Similarity	NPC232872
0.6702	Remote Similarity	NPC306366
0.6701	Remote Similarity	NPC272375
0.6564	Remote Similarity	NPC227778
0.6508	Remote Similarity	NPC70549
0.6477	Remote Similarity	NPC19555
0.6474	Remote Similarity	NPC291359
0.6471	Remote Similarity	NPC184161
0.6468	Remote Similarity	NPC474498
0.6455	Remote Similarity	NPC112766
0.644	Remote Similarity	NPC235628
0.6413	Remote Similarity	NPC473874
0.641	Remote Similarity	NPC257354
0.6394	Remote Similarity	NPC314948
0.638	Remote Similarity	NPC274268
0.6378	Remote Similarity	NPC473769
0.635	Remote Similarity	NPC271958
0.635	Remote Similarity	NPC263507
0.635	Remote Similarity	NPC134413
0.635	Remote Similarity	NPC45112
0.6316	Remote Similarity	NPC478049
0.6311	Remote Similarity	NPC70340
0.6298	Remote Similarity	NPC126637
0.6287	Remote Similarity	NPC86678
0.6287	Remote Similarity	NPC471785
0.6283	Remote Similarity	NPC10875
0.6283	Remote Similarity	NPC10730
0.6281	Remote Similarity	NPC168153
0.6245	Remote Similarity	NPC313627
0.6244	Remote Similarity	NPC269383
0.6244	Remote Similarity	NPC151030
0.6214	Remote Similarity	NPC22928
0.6213	Remote Similarity	NPC222982
0.6181	Remote Similarity	NPC49315
0.6165	Remote Similarity	NPC219170
0.6165	Remote Similarity	NPC180253
0.6158	Remote Similarity	NPC314025
0.6154	Remote Similarity	NPC57105
0.6146	Remote Similarity	NPC313886
0.6146	Remote Similarity	NPC276060
0.6146	Remote Similarity	NPC132751
0.6139	Remote Similarity	NPC472331
0.6139	Remote Similarity	NPC274002
0.6139	Remote Similarity	NPC316161
0.6139	Remote Similarity	NPC126515
0.6138	Remote Similarity	NPC476743
0.6124	Remote Similarity	NPC294244
0.6105	Remote Similarity	NPC476744
0.6103	Remote Similarity	NPC231862
0.6098	Remote Similarity	NPC315913
0.6066	Remote Similarity	NPC322424
0.6066	Remote Similarity	NPC64205
0.6066	Remote Similarity	NPC29472
0.6061	Remote Similarity	NPC227033
0.6058	Remote Similarity	NPC217294
0.6054	Remote Similarity	NPC197921
0.6049	Remote Similarity	NPC314213
0.6049	Remote Similarity	NPC314656
0.6047	Remote Similarity	NPC472329
0.6047	Remote Similarity	NPC472330
0.6042	Remote Similarity	NPC476742
0.6042	Remote Similarity	NPC219383
0.6039	Remote Similarity	NPC288854
0.6038	Remote Similarity	NPC475702
0.6022	Remote Similarity	NPC91953
0.6022	Remote Similarity	NPC469360
0.6017	Remote Similarity	NPC314743
0.6011	Remote Similarity	NPC323798
0.601	Remote Similarity	NPC476741
0.601	Remote Similarity	NPC228040
0.5991	Remote Similarity	NPC159101
0.598	Remote Similarity	NPC314861
0.5973	Remote Similarity	NPC108826
0.5967	Remote Similarity	NPC319774
0.5955	Remote Similarity	NPC325013
0.5951	Remote Similarity	NPC115343
0.5951	Remote Similarity	NPC1291
0.595	Remote Similarity	NPC208280
0.5931	Remote Similarity	NPC110374
0.5931	Remote Similarity	NPC289743
0.5928	Remote Similarity	NPC168250
0.5913	Remote Similarity	NPC28425
0.5913	Remote Similarity	NPC166655
0.5894	Remote Similarity	NPC215747
0.5894	Remote Similarity	NPC311936
0.5894	Remote Similarity	NPC192939
0.5893	Remote Similarity	NPC140888
0.5888	Remote Similarity	NPC476194
0.5888	Remote Similarity	NPC473371
0.5882	Remote Similarity	NPC181526
0.5877	Remote Similarity	NPC112676
0.5877	Remote Similarity	NPC296742
0.5875	Remote Similarity	NPC172355
0.5872	Remote Similarity	NPC311357
0.5865	Remote Similarity	NPC119579
0.5862	Remote Similarity	NPC182257
0.586	Remote Similarity	NPC166667
0.5859	Remote Similarity	NPC156348
0.5858	Remote Similarity	NPC255721
0.5854	Remote Similarity	NPC220560
0.5853	Remote Similarity	NPC469443
0.5852	Remote Similarity	NPC67791
0.5851	Remote Similarity	NPC477838
0.5851	Remote Similarity	NPC477837
0.5845	Remote Similarity	NPC260118
0.5842	Remote Similarity	NPC178466
0.5842	Remote Similarity	NPC63628
0.5829	Remote Similarity	NPC329837
0.5829	Remote Similarity	NPC224293
0.582	Remote Similarity	NPC195814
0.5817	Remote Similarity	NPC98197
0.5816	Remote Similarity	NPC275027
0.5815	Remote Similarity	NPC314552
0.5814	Remote Similarity	NPC474544
0.5814	Remote Similarity	NPC1986
0.5813	Remote Similarity	NPC470081
0.5806	Remote Similarity	NPC6570
0.5805	Remote Similarity	NPC290069
0.5805	Remote Similarity	NPC194724
0.5799	Remote Similarity	NPC96730
0.5798	Remote Similarity	NPC106688
0.5797	Remote Similarity	NPC265383
0.5792	Remote Similarity	NPC470936
0.5792	Remote Similarity	NPC185313
0.5789	Remote Similarity	NPC469829
0.5789	Remote Similarity	NPC320394
0.5782	Remote Similarity	NPC69213
0.5781	Remote Similarity	NPC313414
0.5778	Remote Similarity	NPC174729
0.5778	Remote Similarity	NPC33402
0.5775	Remote Similarity	NPC475411
0.5771	Remote Similarity	NPC70172
0.5769	Remote Similarity	NPC26576
0.5769	Remote Similarity	NPC197680
0.5769	Remote Similarity	NPC477839
0.5769	Remote Similarity	NPC259098
0.5765	Remote Similarity	NPC127402
0.5764	Remote Similarity	NPC473696
0.576	Remote Similarity	NPC323662
0.5755	Remote Similarity	NPC474661
0.5755	Remote Similarity	NPC475919
0.5753	Remote Similarity	NPC214368
0.5753	Remote Similarity	NPC218530
0.575	Remote Similarity	NPC475983
0.5745	Remote Similarity	NPC160607
0.5745	Remote Similarity	NPC204848
0.5745	Remote Similarity	NPC41473
0.5745	Remote Similarity	NPC312770
0.5745	Remote Similarity	NPC14600
0.5744	Remote Similarity	NPC40209
0.5743	Remote Similarity	NPC127362
0.5742	Remote Similarity	NPC469831
0.574	Remote Similarity	NPC76327
0.5735	Remote Similarity	NPC291759
0.5732	Remote Similarity	NPC314702
0.5729	Remote Similarity	NPC471203
0.5728	Remote Similarity	NPC231371
0.5728	Remote Similarity	NPC477115
0.5722	Remote Similarity	NPC159589
0.5721	Remote Similarity	NPC136411
0.5721	Remote Similarity	NPC79293
0.5721	Remote Similarity	NPC328763
0.5721	Remote Similarity	NPC279401
0.5714	Remote Similarity	NPC272706
0.5714	Remote Similarity	NPC314252
0.5714	Remote Similarity	NPC111723
0.5714	Remote Similarity	NPC237517
0.5714	Remote Similarity	NPC123559
0.5714	Remote Similarity	NPC91204
0.5714	Remote Similarity	NPC296898
0.5714	Remote Similarity	NPC298401
0.5714	Remote Similarity	NPC474607
0.5714	Remote Similarity	NPC472405
0.5707	Remote Similarity	NPC158477
0.5707	Remote Similarity	NPC473987
0.5706	Remote Similarity	NPC283760
0.57	Remote Similarity	NPC19023
0.5699	Remote Similarity	NPC285078
0.5699	Remote Similarity	NPC6854
0.5699	Remote Similarity	NPC313737
0.5695	Remote Similarity	NPC219350
0.5695	Remote Similarity	NPC194699
0.5695	Remote Similarity	NPC220060
0.5693	Remote Similarity	NPC179250
0.5693	Remote Similarity	NPC50380

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 NPC295287 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	721
0.2-0.3	1141
0.3-0.4	2433
0.4-0.5	3676
0.5-0.6	897
0.6-0.7	76
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9042	High Similarity	NPD7129	Suspended
0.7005	Intermediate Similarity	NPD7628	Phase 3
0.7005	Intermediate Similarity	NPD7629	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7630	Phase 3
0.6906	Remote Similarity	NPD1159	Approved
0.6881	Remote Similarity	NPD6034	Phase 2
0.6872	Remote Similarity	NPD1835	Phase 1
0.6816	Remote Similarity	NPD5984	Phase 2
0.6723	Remote Similarity	NPD5788	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD1162	Approved
0.67	Remote Similarity	NPD4771	Phase 2
0.6667	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD3560	Approved
0.6614	Remote Similarity	NPD3557	Approved
0.6614	Remote Similarity	NPD3556	Approved
0.6614	Remote Similarity	NPD3558	Approved
0.6562	Remote Similarity	NPD1414	Approved
0.6562	Remote Similarity	NPD1850	Phase 3
0.6562	Remote Similarity	NPD1413	Approved
0.6555	Remote Similarity	NPD2498	Approved
0.6553	Remote Similarity	NPD5872	Discontinued
0.6535	Remote Similarity	NPD5800	Discontinued
0.6533	Remote Similarity	NPD2166	Phase 3
0.6533	Remote Similarity	NPD1381	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD5650	Approved
0.6473	Remote Similarity	NPD5652	Approved
0.6473	Remote Similarity	NPD5651	Approved
0.6455	Remote Similarity	NPD1187	Discontinued
0.645	Remote Similarity	NPD4012	Approved
0.6432	Remote Similarity	NPD2168	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD2167	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD2169	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD6184	Discontinued
0.6404	Remote Similarity	NPD3120	Approved
0.6404	Remote Similarity	NPD3119	Phase 1
0.6402	Remote Similarity	NPD1715	Phase 1
0.6402	Remote Similarity	NPD1714	Approved
0.6382	Remote Similarity	NPD1716	Phase 3
0.6377	Remote Similarity	NPD4523	Approved
0.6359	Remote Similarity	NPD3601	Discontinued
0.635	Remote Similarity	NPD1717	Clinical (unspecified phase)
0.635	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4605	Approved
0.6316	Remote Similarity	NPD4604	Approved
0.6308	Remote Similarity	NPD6905	Phase 2
0.6302	Remote Similarity	NPD6283	Phase 2
0.6293	Remote Similarity	NPD4113	Discontinued
0.6289	Remote Similarity	NPD3453	Discontinued
0.6287	Remote Similarity	NPD7883	Discontinued
0.6287	Remote Similarity	NPD3542	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD6981	Phase 2
0.6275	Remote Similarity	NPD5565	Discontinued
0.6244	Remote Similarity	NPD3065	Discontinued
0.6225	Remote Similarity	NPD6045	Phase 3
0.622	Remote Similarity	NPD6312	Discontinued
0.6214	Remote Similarity	NPD1339	Discontinued
0.6207	Remote Similarity	NPD1361	Discontinued
0.6205	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD3778	Approved
0.6178	Remote Similarity	NPD6056	Approved
0.6178	Remote Similarity	NPD6057	Approved
0.6172	Remote Similarity	NPD4590	Approved
0.6172	Remote Similarity	NPD4591	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD5150	Phase 2
0.6169	Remote Similarity	NPD5670	Approved
0.6157	Remote Similarity	NPD8244	Phase 2
0.614	Remote Similarity	NPD6289	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD1898	Discontinued
0.6133	Remote Similarity	NPD1555	Discontinued
0.6131	Remote Similarity	NPD2215	Approved
0.6131	Remote Similarity	NPD2216	Approved
0.6117	Remote Similarity	NPD3154	Approved
0.6117	Remote Similarity	NPD3153	Approved
0.6109	Remote Similarity	NPD2615	Phase 3
0.6109	Remote Similarity	NPD2616	Phase 3
0.6095	Remote Similarity	NPD7125	Discontinued
0.6087	Remote Similarity	NPD4951	Discontinued
0.6078	Remote Similarity	NPD6104	Discontinued
0.6062	Remote Similarity	NPD3538	Suspended
0.6061	Remote Similarity	NPD8067	Phase 3
0.6059	Remote Similarity	NPD2825	Approved
0.6059	Remote Similarity	NPD2827	Approved
0.6059	Remote Similarity	NPD2826	Approved
0.6058	Remote Similarity	NPD408	Approved
0.605	Remote Similarity	NPD4083	Discontinued
0.6044	Remote Similarity	NPD1106	Discontinued
0.6038	Remote Similarity	NPD4931	Phase 2
0.6021	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.602	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD2374	Approved
0.6019	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD2579	Approved
0.601	Remote Similarity	NPD1615	Approved
0.5981	Remote Similarity	NPD712	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD2727	Phase 2
0.5979	Remote Similarity	NPD3296	Phase 1
0.5978	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.5967	Remote Similarity	NPD2372	Approved
0.596	Remote Similarity	NPD4064	Discontinued
0.5959	Remote Similarity	NPD4003	Phase 3
0.5959	Remote Similarity	NPD950	Clinical (unspecified phase)
0.595	Remote Similarity	NPD5623	Approved
0.5941	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD1477	Approved
0.5926	Remote Similarity	NPD4914	Approved
0.5926	Remote Similarity	NPD5542	Phase 2
0.5917	Remote Similarity	NPD3804	Discontinued
0.5902	Remote Similarity	NPD839	Approved
0.5902	Remote Similarity	NPD840	Approved
0.5899	Remote Similarity	NPD7476	Discontinued
0.5897	Remote Similarity	NPD3579	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD302	Approved
0.5888	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5845	Phase 2
0.5877	Remote Similarity	NPD4259	Approved
0.5877	Remote Similarity	NPD4258	Approved
0.5871	Remote Similarity	NPD2034	Discontinued
0.5867	Remote Similarity	NPD2672	Discontinued
0.586	Remote Similarity	NPD2941	Discontinued
0.586	Remote Similarity	NPD3552	Approved
0.586	Remote Similarity	NPD827	Approved
0.586	Remote Similarity	NPD3553	Approved
0.586	Remote Similarity	NPD3554	Approved
0.586	Remote Similarity	NPD3555	Approved
0.5837	Remote Similarity	NPD8167	Discontinued
0.5826	Remote Similarity	NPD7221	Approved
0.5826	Remote Similarity	NPD7219	Approved
0.5822	Remote Similarity	NPD3819	Phase 2
0.5822	Remote Similarity	NPD5214	Phase 2
0.5822	Remote Similarity	NPD4740	Approved
0.5816	Remote Similarity	NPD5617	Suspended
0.5816	Remote Similarity	NPD3684	Discontinued
0.5815	Remote Similarity	NPD5545	Phase 2
0.5815	Remote Similarity	NPD5164	Discontinued
0.5815	Remote Similarity	NPD829	Discontinued
0.5813	Remote Similarity	NPD3975	Discontinued
0.5808	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD2176	Approved
0.5806	Remote Similarity	NPD2177	Approved
0.5806	Remote Similarity	NPD2175	Phase 3
0.5803	Remote Similarity	NPD681	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD2845	Phase 2
0.5802	Remote Similarity	NPD2843	Phase 2
0.5802	Remote Similarity	NPD1213	Phase 3
0.5799	Remote Similarity	NPD3928	Approved
0.5799	Remote Similarity	NPD3931	Approved
0.5799	Remote Similarity	NPD4387	Approved
0.5799	Remote Similarity	NPD4386	Approved
0.5798	Remote Similarity	NPD1422	Approved
0.5787	Remote Similarity	NPD6072	Discontinued
0.5787	Remote Similarity	NPD3236	Phase 3
0.5787	Remote Similarity	NPD3237	Clinical (unspecified phase)
0.5787	Remote Similarity	NPD2789	Approved
0.5787	Remote Similarity	NPD1229	Phase 2
0.5782	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.5782	Remote Similarity	NPD4587	Phase 3
0.5781	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD5871	Discontinued
0.5769	Remote Similarity	NPD1533	Clinical (unspecified phase)
0.5767	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD6736	Discontinued
0.5758	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD3398	Discontinued
0.5752	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.5751	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.5749	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD9342	Approved
0.5743	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.5742	Remote Similarity	NPD2802	Phase 3
0.5742	Remote Similarity	NPD6461	Clinical (unspecified phase)
0.574	Remote Similarity	NPD9507	Approved
0.574	Remote Similarity	NPD9532	Phase 3
0.5736	Remote Similarity	NPD4675	Approved
0.5736	Remote Similarity	NPD4678	Approved
0.5734	Remote Similarity	NPD9687	Approved
0.5734	Remote Similarity	NPD9688	Approved
0.5733	Remote Similarity	NPD4502	Phase 2
0.5733	Remote Similarity	NPD7548	Discontinued
0.573	Remote Similarity	NPD6405	Approved
0.573	Remote Similarity	NPD6407	Approved
0.5729	Remote Similarity	NPD4485	Approved
0.5728	Remote Similarity	NPD5132	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD1852	Discontinued
0.5722	Remote Similarity	NPD471	Approved
0.5721	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD7262	Phase 1
0.5714	Remote Similarity	NPD7805	Phase 3
0.5707	Remote Similarity	NPD3136	Phase 2
0.5707	Remote Similarity	NPD2326	Approved
0.5707	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.5707	Remote Similarity	NPD6913	Approved
0.5707	Remote Similarity	NPD5858	Discontinued
0.57	Remote Similarity	NPD5560	Clinical (unspecified phase)
0.57	Remote Similarity	NPD5599	Discontinued
0.57	Remote Similarity	NPD5498	Phase 2

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