NPASS Compound

Structure

CID174629 OpenBabel06191715552D 29 33 0 0 1 0 0 0 0 0999 V2000 2.1777 3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4649 2.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2294 3.0074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3486 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7608 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4158 2.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1590 2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7608 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8176 2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1266 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4867 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 2.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8097 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0777 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1266 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9437 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9437 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 2 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 4.8097 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.0777 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9437 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9437 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2784 3.3164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 29 1 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 24 1 0 0 0 0 9 12 2 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 17 2 0 0 0 0 13 29 1 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 5 1 6 0 0 0 16 20 1 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 22 1 6 0 0 0 18 25 1 0 0 0 0 19 24 1 0 0 0 0 19 26 2 0 0 0 0 20 25 1 0 0 0 0 20 27 2 0 0 0 0 21 22 1 0 0 0 0 21 23 2 0 0 0 0 21 28 1 0 0 0 0 22 11 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	393.17
Volume:	393.345
LogP:	2.69
LogD:	2.404
LogS:	-4.309
# Rotatable Bonds:	2
TPSA:	78.95
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.779
Synthetic Accessibility Score:	4.536
Fsp3:	0.409
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.043
MDCK Permeability:	1.8225291569251567e-05
Pgp-inhibitor:	0.668
Pgp-substrate:	0.665
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.239
30% Bioavailability (F30%):	0.945

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.948
Plasma Protein Binding (PPB):	85.81043243408203%
Volume Distribution (VD):	1.036
Pgp-substrate:	16.750686645507812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.642
CYP2C19-inhibitor:	0.489
CYP2C19-substrate:	0.878
CYP2C9-inhibitor:	0.257
CYP2C9-substrate:	0.695
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.199
CYP3A4-inhibitor:	0.454
CYP3A4-substrate:	0.926

ADMET: Excretion

Clearance (CL):	7.943
Half-life (T1/2):	0.128

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.951
Drug-inuced Liver Injury (DILI):	0.883
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.727
Maximum Recommended Daily Dose:	0.593
Skin Sensitization:	0.745
Carcinogencity:	0.692
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.529

Download Data

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

Natural Product: NPC174629

Natural Product ID:	NPC174629
*Common Name:**	Spirotryprostatin B
IUPAC Name:	(3S,3'S,5'aS)-6-methoxy-3'-(2-methylprop-1-enyl)spiro[1H-indole-3,2'-5a,6,7,8-tetrahydro-3H-dipyrrolo[1,2-c:1',3'-f]pyrazine]-2,5',10'-trione
Synonyms:
Standard InCHIKey:	UHQKDPCPFNXIDU-ZJBJCVSYSA-N
Standard InCHI:	InChI=1S/C22H23N3O4/c1-12(2)9-18-22(14-7-6-13(29-3)10-15(14)23-21(22)28)11-17-19(26)24-8-4-5-16(24)20(27)25(17)18/h6-7,9-11,16,18H,4-5,8H2,1-3H3,(H,23,28)/t16-,18-,22-/m0/s1
SMILES:	CC(=C[C@H]1[C@]2(C=C3C(=O)N4CCC[C@H]4C(=O)N13)c1ccc(cc1N=C2O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL488302
PubChem CID:	24900164
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino 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
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17616609]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17929896]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18505285]
NPO32792	aspergillus sydowi	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18505285]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113967]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159274]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19256529]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	isolated from sediment collected using a hand held deep water sampling device at >33 m depth in Vanuatu	2003	PMID[20303767]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954885]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22106303]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	stem bark of Melia azedarach	n.a.	n.a.	PMID[22409377]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23557488]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23563483]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23647825]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24057165]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7622436]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	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	8
Others	2

Activity Type	# Activity
Cell Line	4
Individual Protein	1
Organism	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	8290.0	nM	PMID[508864]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	9710.0	nM	PMID[508864]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	41000.0	nM	PMID[508865]
NPT470	Individual Protein	Rhodesain	Trypanosoma brucei rhodesiense	IC50	>	50000.0	nM	PMID[508866]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	21100.0	nM	PMID[508866]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	5700.0	nM	PMID[508866]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[508866]
NPT2	Others	Unspecified		Ratio IC50	=	3.7	uM	PMID[508866]
NPT610	Others	Molecular identity unknown		IC50	=	14000.0	nM	PMID[508867]
NPT176	Organism	Artemia salina	Artemia salina	LC50	>	100.0	ug.mL-1	PMID[508868]

☑ 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 NPC174629 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	296
0.1-0.2	1376
0.2-0.3	6081
0.3-0.4	10852
0.4-0.5	14775
0.5-0.6	7566
0.6-0.7	1592
0.7-0.8	148
0.8-0.85	9
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9314	High Similarity	NPC204970
0.8324	Intermediate Similarity	NPC39822
0.7868	Intermediate Similarity	NPC205926
0.7849	Intermediate Similarity	NPC473007
0.7831	Intermediate Similarity	NPC28510
0.7806	Intermediate Similarity	NPC14339
0.7789	Intermediate Similarity	NPC476651
0.7778	Intermediate Similarity	NPC473008
0.7772	Intermediate Similarity	NPC100863
0.7745	Intermediate Similarity	NPC37957
0.774	Intermediate Similarity	NPC243673
0.774	Intermediate Similarity	NPC63210
0.774	Intermediate Similarity	NPC310403
0.774	Intermediate Similarity	NPC148468
0.774	Intermediate Similarity	NPC97380
0.774	Intermediate Similarity	NPC263709
0.7718	Intermediate Similarity	NPC250960
0.7718	Intermediate Similarity	NPC71539
0.7696	Intermediate Similarity	NPC473004
0.7667	Intermediate Similarity	NPC470069
0.7667	Intermediate Similarity	NPC52059
0.7608	Intermediate Similarity	NPC266994
0.7584	Intermediate Similarity	NPC211525
0.7584	Intermediate Similarity	NPC153694
0.7573	Intermediate Similarity	NPC153923
0.7571	Intermediate Similarity	NPC161827
0.7536	Intermediate Similarity	NPC74216
0.7512	Intermediate Similarity	NPC470001
0.7512	Intermediate Similarity	NPC470002
0.75	Intermediate Similarity	NPC473569
0.7487	Intermediate Similarity	NPC473460
0.7476	Intermediate Similarity	NPC122886
0.7474	Intermediate Similarity	NPC203972
0.7459	Intermediate Similarity	NPC210415
0.7459	Intermediate Similarity	NPC293255
0.7459	Intermediate Similarity	NPC298851
0.7459	Intermediate Similarity	NPC21752
0.7459	Intermediate Similarity	NPC276993
0.7459	Intermediate Similarity	NPC181138
0.7437	Intermediate Similarity	NPC473005
0.7436	Intermediate Similarity	NPC243626
0.7436	Intermediate Similarity	NPC230313
0.7424	Intermediate Similarity	NPC127178
0.7424	Intermediate Similarity	NPC67904
0.7391	Intermediate Similarity	NPC305984
0.7371	Intermediate Similarity	NPC22476
0.7371	Intermediate Similarity	NPC194740
0.7356	Intermediate Similarity	NPC303658
0.7336	Intermediate Similarity	NPC470821
0.7321	Intermediate Similarity	NPC219397
0.7308	Intermediate Similarity	NPC126556
0.7304	Intermediate Similarity	NPC471561
0.7277	Intermediate Similarity	NPC87714
0.7268	Intermediate Similarity	NPC472121
0.7264	Intermediate Similarity	NPC295898
0.7241	Intermediate Similarity	NPC477161
0.7233	Intermediate Similarity	NPC82541
0.722	Intermediate Similarity	NPC477160
0.7215	Intermediate Similarity	NPC184680
0.7198	Intermediate Similarity	NPC470482
0.7198	Intermediate Similarity	NPC470481
0.7194	Intermediate Similarity	NPC203628
0.7192	Intermediate Similarity	NPC473422
0.719	Intermediate Similarity	NPC77777
0.7186	Intermediate Similarity	NPC161804
0.7184	Intermediate Similarity	NPC269449
0.7182	Intermediate Similarity	NPC470785
0.7182	Intermediate Similarity	NPC474183
0.7182	Intermediate Similarity	NPC470784
0.7178	Intermediate Similarity	NPC474077
0.7174	Intermediate Similarity	NPC289776
0.7174	Intermediate Similarity	NPC191863
0.7174	Intermediate Similarity	NPC133470
0.717	Intermediate Similarity	NPC46259
0.7136	Intermediate Similarity	NPC168250
0.7135	Intermediate Similarity	NPC28368
0.7135	Intermediate Similarity	NPC270301
0.7129	Intermediate Similarity	NPC189661
0.7128	Intermediate Similarity	NPC21425
0.7123	Intermediate Similarity	NPC318525
0.7123	Intermediate Similarity	NPC10653
0.7115	Intermediate Similarity	NPC159815
0.7115	Intermediate Similarity	NPC119722
0.7115	Intermediate Similarity	NPC264176
0.7113	Intermediate Similarity	NPC102760
0.7108	Intermediate Similarity	NPC475147
0.71	Intermediate Similarity	NPC272706
0.7097	Intermediate Similarity	NPC254700
0.7092	Intermediate Similarity	NPC217294
0.7081	Intermediate Similarity	NPC473006
0.7079	Intermediate Similarity	NPC138830
0.7072	Intermediate Similarity	NPC49583
0.707	Intermediate Similarity	NPC115588
0.7059	Intermediate Similarity	NPC41216
0.705	Intermediate Similarity	NPC303214
0.7044	Intermediate Similarity	NPC232600
0.7043	Intermediate Similarity	NPC472923
0.7041	Intermediate Similarity	NPC4910
0.7041	Intermediate Similarity	NPC329731
0.7035	Intermediate Similarity	NPC470485
0.7033	Intermediate Similarity	NPC10732
0.7024	Intermediate Similarity	NPC163829
0.701	Intermediate Similarity	NPC98197
0.7005	Intermediate Similarity	NPC70172
0.7	Intermediate Similarity	NPC324081
0.699	Remote Similarity	NPC158551
0.6986	Remote Similarity	NPC471532
0.6983	Remote Similarity	NPC9373
0.698	Remote Similarity	NPC71124
0.6978	Remote Similarity	NPC219383
0.6977	Remote Similarity	NPC148124
0.6971	Remote Similarity	NPC475133
0.6971	Remote Similarity	NPC174758
0.6971	Remote Similarity	NPC469589
0.697	Remote Similarity	NPC474059
0.6963	Remote Similarity	NPC128115
0.6952	Remote Similarity	NPC127996
0.6951	Remote Similarity	NPC151171
0.6942	Remote Similarity	NPC268077
0.6942	Remote Similarity	NPC470484
0.6935	Remote Similarity	NPC470483
0.6934	Remote Similarity	NPC152768
0.6934	Remote Similarity	NPC148183
0.693	Remote Similarity	NPC99724
0.693	Remote Similarity	NPC128476
0.6927	Remote Similarity	NPC311357
0.6923	Remote Similarity	NPC329329
0.6923	Remote Similarity	NPC317709
0.6919	Remote Similarity	NPC477186
0.6919	Remote Similarity	NPC319320
0.6919	Remote Similarity	NPC287757
0.6916	Remote Similarity	NPC108826
0.6915	Remote Similarity	NPC198401
0.6901	Remote Similarity	NPC313327
0.6898	Remote Similarity	NPC315498
0.6898	Remote Similarity	NPC230942
0.6893	Remote Similarity	NPC207971
0.6889	Remote Similarity	NPC472100
0.6878	Remote Similarity	NPC278887
0.6866	Remote Similarity	NPC254957
0.6863	Remote Similarity	NPC5374
0.6854	Remote Similarity	NPC471531
0.6854	Remote Similarity	NPC234772
0.6849	Remote Similarity	NPC248903
0.6842	Remote Similarity	NPC231198
0.684	Remote Similarity	NPC471080
0.684	Remote Similarity	NPC469592
0.6837	Remote Similarity	NPC288110
0.6835	Remote Similarity	NPC21638
0.6832	Remote Similarity	NPC184933
0.6832	Remote Similarity	NPC59827
0.6827	Remote Similarity	NPC195787
0.6827	Remote Similarity	NPC246140
0.6825	Remote Similarity	NPC299582
0.6818	Remote Similarity	NPC291759
0.6818	Remote Similarity	NPC471762
0.681	Remote Similarity	NPC174672
0.6806	Remote Similarity	NPC471568
0.6806	Remote Similarity	NPC473693
0.6804	Remote Similarity	NPC26928
0.6804	Remote Similarity	NPC9475
0.68	Remote Similarity	NPC5630
0.6794	Remote Similarity	NPC478075
0.6791	Remote Similarity	NPC473041
0.6791	Remote Similarity	NPC469594
0.6786	Remote Similarity	NPC291173
0.6778	Remote Similarity	NPC472103
0.6776	Remote Similarity	NPC274982
0.6774	Remote Similarity	NPC10730
0.6774	Remote Similarity	NPC10875
0.6771	Remote Similarity	NPC85482
0.6769	Remote Similarity	NPC475421
0.6768	Remote Similarity	NPC133591
0.6766	Remote Similarity	NPC477526
0.6758	Remote Similarity	NPC19175
0.6757	Remote Similarity	NPC476268
0.6754	Remote Similarity	NPC186617
0.6754	Remote Similarity	NPC33507
0.6751	Remote Similarity	NPC167763
0.6751	Remote Similarity	NPC470903
0.6751	Remote Similarity	NPC470112
0.6744	Remote Similarity	NPC195636
0.6739	Remote Similarity	NPC262166
0.6739	Remote Similarity	NPC261934
0.6739	Remote Similarity	NPC5194
0.6735	Remote Similarity	NPC70092
0.6734	Remote Similarity	NPC38823
0.6734	Remote Similarity	NPC207033
0.6732	Remote Similarity	NPC477527
0.6729	Remote Similarity	NPC314817
0.6729	Remote Similarity	NPC316297
0.6729	Remote Similarity	NPC66191
0.6719	Remote Similarity	NPC475123
0.6719	Remote Similarity	NPC475204
0.6714	Remote Similarity	NPC472098
0.6714	Remote Similarity	NPC198160
0.6714	Remote Similarity	NPC16249
0.6702	Remote Similarity	NPC301163
0.6702	Remote Similarity	NPC472114
0.6702	Remote Similarity	NPC472115

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 NPC174629 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	511
0.2-0.3	735
0.3-0.4	1417
0.4-0.5	2609
0.5-0.6	3040
0.6-0.7	637
0.7-0.8	16
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
0.75	Intermediate Similarity	NPD5967	Approved
0.7413	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD5617	Suspended
0.7358	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5811	Approved
0.7166	Intermediate Similarity	NPD5186	Approved
0.7166	Intermediate Similarity	NPD5183	Approved
0.7107	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7281	Phase 3
0.7062	Intermediate Similarity	NPD7280	Phase 3
0.7056	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4539	Phase 1
0.7016	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD3793	Phase 3
0.6978	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6457	Approved
0.6931	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD3983	Phase 3
0.6931	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1670	Discontinued
0.6919	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4796	Discontinued
0.6912	Remote Similarity	NPD6519	Phase 2
0.6907	Remote Similarity	NPD6878	Phase 2
0.6907	Remote Similarity	NPD6879	Phase 2
0.6898	Remote Similarity	NPD1743	Approved
0.6898	Remote Similarity	NPD1742	Approved
0.6898	Remote Similarity	NPD19	Approved
0.6891	Remote Similarity	NPD5600	Discontinued
0.6887	Remote Similarity	NPD7559	Phase 2
0.6885	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD3037	Phase 1
0.6872	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5025	Approved
0.6853	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD3441	Approved
0.6833	Remote Similarity	NPD3442	Approved
0.6831	Remote Similarity	NPD7131	Phase 3
0.6828	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6297	Approved
0.6816	Remote Similarity	NPD7569	Approved
0.6816	Remote Similarity	NPD7570	Approved
0.6814	Remote Similarity	NPD5071	Phase 2
0.6812	Remote Similarity	NPD3802	Phase 3
0.681	Remote Similarity	NPD3591	Approved
0.681	Remote Similarity	NPD3592	Approved
0.6806	Remote Similarity	NPD3437	Discontinued
0.6804	Remote Similarity	NPD3965	Phase 1
0.6802	Remote Similarity	NPD4885	Approved
0.6796	Remote Similarity	NPD6238	Discontinued
0.6796	Remote Similarity	NPD6321	Discontinued
0.6788	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD4515	Suspended
0.6782	Remote Similarity	NPD3631	Phase 3
0.6778	Remote Similarity	NPD5481	Discontinued
0.6776	Remote Similarity	NPD8149	Discontinued
0.677	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.677	Remote Similarity	NPD8016	Phase 3
0.6769	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6790	Phase 1
0.6733	Remote Similarity	NPD5587	Approved
0.672	Remote Similarity	NPD2592	Discontinued
0.6719	Remote Similarity	NPD4166	Phase 2
0.6718	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7225	Discontinued
0.6712	Remote Similarity	NPD3912	Discontinued
0.6701	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6874	Approved
0.6698	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2215	Approved
0.6684	Remote Similarity	NPD7479	Phase 2
0.6684	Remote Similarity	NPD2216	Approved
0.6683	Remote Similarity	NPD6851	Approved
0.6683	Remote Similarity	NPD6853	Approved
0.6683	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD8027	Approved
0.6667	Remote Similarity	NPD7126	Discontinued
0.6667	Remote Similarity	NPD2821	Approved
0.6667	Remote Similarity	NPD4157	Discontinued
0.665	Remote Similarity	NPD5565	Discontinued
0.665	Remote Similarity	NPD5445	Approved
0.665	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6894	Phase 1
0.6649	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD3416	Discontinued
0.6634	Remote Similarity	NPD2843	Phase 2
0.6634	Remote Similarity	NPD5582	Discontinued
0.6634	Remote Similarity	NPD2845	Phase 2
0.6633	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD3259	Approved
0.6618	Remote Similarity	NPD7810	Phase 3
0.6618	Remote Similarity	NPD7811	Phase 3
0.6617	Remote Similarity	NPD3119	Phase 1
0.6617	Remote Similarity	NPD3120	Approved
0.6616	Remote Similarity	NPD4203	Approved
0.6616	Remote Similarity	NPD4204	Approved
0.6615	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD3141	Discontinued
0.661	Remote Similarity	NPD8255	Phase 2
0.6606	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5658	Approved
0.6599	Remote Similarity	NPD1716	Phase 3
0.6588	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5601	Phase 2
0.6584	Remote Similarity	NPD3349	Phase 2
0.6579	Remote Similarity	NPD6063	Approved
0.6578	Remote Similarity	NPD7797	Approved
0.6578	Remote Similarity	NPD7796	Approved
0.6576	Remote Similarity	NPD5297	Approved
0.6574	Remote Similarity	NPD4897	Phase 2
0.6569	Remote Similarity	NPD5937	Approved
0.6567	Remote Similarity	NPD3153	Approved
0.6567	Remote Similarity	NPD3154	Approved
0.6566	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD7820	Phase 3
0.6558	Remote Similarity	NPD7605	Discovery
0.6552	Remote Similarity	NPD8359	Phase 2
0.655	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD6744	Clinical (unspecified phase)
0.654	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD743	Approved
0.6535	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.653	Remote Similarity	NPD5519	Discontinued
0.6528	Remote Similarity	NPD2904	Discontinued
0.6526	Remote Similarity	NPD6737	Phase 2
0.6526	Remote Similarity	NPD5772	Approved
0.6526	Remote Similarity	NPD5773	Approved
0.6526	Remote Similarity	NPD6738	Phase 2
0.6525	Remote Similarity	NPD8463	Approved
0.6524	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5515	Phase 2
0.6519	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD8311	Discontinued
0.6515	Remote Similarity	NPD5557	Phase 1
0.6513	Remote Similarity	NPD4083	Discontinued
0.6513	Remote Similarity	NPD2388	Discontinued
0.6512	Remote Similarity	NPD683	Approved
0.6509	Remote Similarity	NPD8161	Suspended
0.6507	Remote Similarity	NPD6612	Phase 2
0.6502	Remote Similarity	NPD7291	Discontinued
0.65	Remote Similarity	NPD4012	Approved
0.6495	Remote Similarity	NPD7484	Phase 3
0.6495	Remote Similarity	NPD7485	Phase 3
0.6492	Remote Similarity	NPD3560	Approved
0.6492	Remote Similarity	NPD3558	Approved
0.6492	Remote Similarity	NPD3556	Approved
0.6492	Remote Similarity	NPD3557	Approved
0.6492	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD2097	Approved
0.6489	Remote Similarity	NPD6357	Discontinued
0.6488	Remote Similarity	NPD4740	Approved
0.6482	Remote Similarity	NPD2169	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD1717	Clinical (unspecified phase)
0.648	Remote Similarity	NPD2898	Approved
0.648	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.648	Remote Similarity	NPD2248	Approved
0.648	Remote Similarity	NPD2246	Approved
0.6476	Remote Similarity	NPD4373	Phase 2
0.6476	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD6834	Approved
0.6471	Remote Similarity	NPD7556	Discontinued
0.6471	Remote Similarity	NPD7617	Discontinued
0.6468	Remote Similarity	NPD5562	Approved
0.6468	Remote Similarity	NPD7546	Discontinued
0.6468	Remote Similarity	NPD5561	Approved
0.6465	Remote Similarity	NPD5312	Approved
0.6465	Remote Similarity	NPD5313	Approved
0.6465	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD4368	Phase 2
0.6462	Remote Similarity	NPD4465	Phase 2
0.6462	Remote Similarity	NPD4467	Phase 2
0.6462	Remote Similarity	NPD7608	Discontinued
0.6456	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD4591	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data