NPASS Compound

Structure

NPC122886 OpenBabel07101718322D 31 35 0 0 1 0 0 0 0 0999 V2000 0.3872 1.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6758 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8097 -0.0000 0.0000 C 0 0 0 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 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 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 -0.5909 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8097 -1.0000 0.0000 C 0 0 0 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 -3.0777 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 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 -2.1266 -1.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -1.8176 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6758 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 31 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 12 1 0 0 0 0 7 13 1 0 0 0 0 8 24 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 12 31 1 0 0 0 0 13 14 2 0 0 0 0 13 17 1 0 0 0 0 14 23 1 0 0 0 0 15 5 1 6 0 0 0 15 18 1 0 0 0 0 15 24 1 0 0 0 0 16 21 1 6 0 0 0 16 25 1 0 0 0 0 17 26 2 0 0 0 0 18 25 1 0 0 0 0 18 27 2 0 0 0 0 19 21 1 1 0 0 0 19 22 1 0 0 0 0 19 28 1 0 0 0 0 20 22 1 0 0 0 0 20 24 1 0 0 0 0 20 29 2 0 0 0 0 21 17 1 6 0 0 0 21 23 1 0 0 0 0 22 25 1 0 0 0 0 22 30 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	427.17
Volume:	413.562
LogP:	2.79
LogD:	1.935
LogS:	-3.946
# Rotatable Bonds:	2
TPSA:	119.41
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.58
Synthetic Accessibility Score:	5.09
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.39
MDCK Permeability:	3.983934675488854e-06
Pgp-inhibitor:	0.35
Pgp-substrate:	0.744
Human Intestinal Absorption (HIA):	0.715
20% Bioavailability (F20%):	0.45
30% Bioavailability (F30%):	0.908

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.16
Plasma Protein Binding (PPB):	85.84134674072266%
Volume Distribution (VD):	1.259
Pgp-substrate:	10.137152671813965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.151
CYP2C19-substrate:	0.788
CYP2C9-inhibitor:	0.205
CYP2C9-substrate:	0.141
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.304
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	5.052
Half-life (T1/2):	0.425

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.861
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.227
Maximum Recommended Daily Dose:	0.665
Skin Sensitization:	0.515
Carcinogencity:	0.701
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.683

Download Data

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

Natural Product: NPC122886

Natural Product ID:	NPC122886
*Common Name:**	(1S,2S,3S,5As,10Ar)-1,10A-Dihydroxy-6'-Methoxy-3-(2-Methylprop-1-Enyl)Spiro[1,3,5A,6,7,8-Hexahydrodipyrrolo[1,2-D:1',2'-F]Pyrazine-2,2'-1H-Indole]-3',5,10-Trione
IUPAC Name:	(1S,2S,3S,5aS,10aR)-1,10a-dihydroxy-6'-methoxy-3-(2-methylprop-1-enyl)spiro[1,3,5a,6,7,8-hexahydrodipyrrolo[1,2-d:1',2'-f]pyrazine-2,2'-1H-indole]-3',5,10-trione
Synonyms:
Standard InCHIKey:	XPLQKNTVQRYSHU-CTSLQZMRSA-N
Standard InCHI:	InChI=1S/C22H25N3O6/c1-11(2)9-16-21(17(26)13-7-6-12(31-3)10-14(13)23-21)19(28)22(30)20(29)24-8-4-5-15(24)18(27)25(16)22/h6-7,9-10,15-16,19,23,28,30H,4-5,8H2,1-3H3/t15-,16-,19-,21+,22+/m0/s1
SMILES:	COc1ccc2c(c1)N[C@@]1(C2=O)[C@H](C=C(C)C)N2[C@]([C@H]1O)(O)C(=O)N1[C@H](C2=O)CCC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2229122
PubChem CID:	25034615
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]
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]
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]
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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1769	Organism	Mythimna separata	Mythimna separata	AFI	=	5.0	%	PMID[470988]
NPT176	Organism	Artemia salina	Artemia salina	LC50	>	100.0	ug.mL-1	PMID[470988]

☑ 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 NPC122886 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	334
0.1-0.2	1783
0.2-0.3	8325
0.3-0.4	9636
0.4-0.5	13754
0.5-0.6	7561
0.6-0.7	1200
0.7-0.8	102
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8155	Intermediate Similarity	NPC100863
0.8019	Intermediate Similarity	NPC478075
0.7982	Intermediate Similarity	NPC77777
0.7793	Intermediate Similarity	NPC41216
0.774	Intermediate Similarity	NPC204970
0.7706	Intermediate Similarity	NPC470784
0.7696	Intermediate Similarity	NPC291173
0.7696	Intermediate Similarity	NPC477160
0.7674	Intermediate Similarity	NPC87714
0.7667	Intermediate Similarity	NPC243626
0.7662	Intermediate Similarity	NPC184680
0.7639	Intermediate Similarity	NPC477161
0.7629	Intermediate Similarity	NPC151171
0.7629	Intermediate Similarity	NPC470785
0.7623	Intermediate Similarity	NPC219397
0.7523	Intermediate Similarity	NPC189661
0.7511	Intermediate Similarity	NPC194740
0.75	Intermediate Similarity	NPC230313
0.7478	Intermediate Similarity	NPC128476
0.7478	Intermediate Similarity	NPC46259
0.7476	Intermediate Similarity	NPC174629
0.7467	Intermediate Similarity	NPC288110
0.7455	Intermediate Similarity	NPC126556
0.7452	Intermediate Similarity	NPC473007
0.7432	Intermediate Similarity	NPC127996
0.7406	Intermediate Similarity	NPC473004
0.7404	Intermediate Similarity	NPC474183
0.7399	Intermediate Similarity	NPC217903
0.7393	Intermediate Similarity	NPC473008
0.7391	Intermediate Similarity	NPC473458
0.7384	Intermediate Similarity	NPC469722
0.738	Intermediate Similarity	NPC115588
0.738	Intermediate Similarity	NPC19175
0.7358	Intermediate Similarity	NPC22476
0.7354	Intermediate Similarity	NPC116178
0.7354	Intermediate Similarity	NPC470481
0.7354	Intermediate Similarity	NPC470482
0.7352	Intermediate Similarity	NPC14339
0.7342	Intermediate Similarity	NPC269449
0.7327	Intermediate Similarity	NPC67904
0.7319	Intermediate Similarity	NPC154922
0.7318	Intermediate Similarity	NPC195787
0.7318	Intermediate Similarity	NPC246140
0.7301	Intermediate Similarity	NPC195636
0.7285	Intermediate Similarity	NPC198160
0.7277	Intermediate Similarity	NPC10732
0.7277	Intermediate Similarity	NPC119722
0.7273	Intermediate Similarity	NPC314659
0.7255	Intermediate Similarity	NPC472118
0.7244	Intermediate Similarity	NPC321166
0.7241	Intermediate Similarity	NPC471513
0.7237	Intermediate Similarity	NPC475609
0.723	Intermediate Similarity	NPC45389
0.7225	Intermediate Similarity	NPC197335
0.7205	Intermediate Similarity	NPC476069
0.7196	Intermediate Similarity	NPC203628
0.7195	Intermediate Similarity	NPC268077
0.7195	Intermediate Similarity	NPC475147
0.7193	Intermediate Similarity	NPC303658
0.7181	Intermediate Similarity	NPC234772
0.717	Intermediate Similarity	NPC87391
0.7167	Intermediate Similarity	NPC113455
0.7167	Intermediate Similarity	NPC470480
0.7162	Intermediate Similarity	NPC222046
0.7155	Intermediate Similarity	NPC231924
0.7149	Intermediate Similarity	NPC207971
0.7143	Intermediate Similarity	NPC148124
0.7136	Intermediate Similarity	NPC232600
0.713	Intermediate Similarity	NPC10653
0.713	Intermediate Similarity	NPC318525
0.7129	Intermediate Similarity	NPC475094
0.7124	Intermediate Similarity	NPC159815
0.7113	Intermediate Similarity	NPC301501
0.7108	Intermediate Similarity	NPC299582
0.7107	Intermediate Similarity	NPC329932
0.7107	Intermediate Similarity	NPC477393
0.71	Intermediate Similarity	NPC329830
0.71	Intermediate Similarity	NPC99724
0.7095	Intermediate Similarity	NPC469451
0.7083	Intermediate Similarity	NPC114039
0.7083	Intermediate Similarity	NPC206109
0.708	Intermediate Similarity	NPC295479
0.708	Intermediate Similarity	NPC220241
0.7078	Intermediate Similarity	NPC112937
0.7078	Intermediate Similarity	NPC138615
0.7078	Intermediate Similarity	NPC265642
0.7078	Intermediate Similarity	NPC132874
0.7078	Intermediate Similarity	NPC218733
0.7078	Intermediate Similarity	NPC120239
0.7078	Intermediate Similarity	NPC71124
0.7074	Intermediate Similarity	NPC305984
0.707	Intermediate Similarity	NPC474059
0.7067	Intermediate Similarity	NPC475133
0.7064	Intermediate Similarity	NPC303214
0.7059	Intermediate Similarity	NPC476220
0.7059	Intermediate Similarity	NPC160113
0.7054	Intermediate Similarity	NPC212123
0.7049	Intermediate Similarity	NPC477396
0.7043	Intermediate Similarity	NPC182853
0.704	Intermediate Similarity	NPC163829
0.7037	Intermediate Similarity	NPC1820
0.7027	Intermediate Similarity	NPC473005
0.7027	Intermediate Similarity	NPC1464
0.7025	Intermediate Similarity	NPC477395
0.7025	Intermediate Similarity	NPC469452
0.7021	Intermediate Similarity	NPC248903
0.7019	Intermediate Similarity	NPC73280
0.7018	Intermediate Similarity	NPC473006
0.7014	Intermediate Similarity	NPC138830
0.7014	Intermediate Similarity	NPC127178
0.7013	Intermediate Similarity	NPC37957
0.7012	Intermediate Similarity	NPC469450
0.699	Remote Similarity	NPC214960
0.699	Remote Similarity	NPC279527
0.6987	Remote Similarity	NPC298449
0.6979	Remote Similarity	NPC26928
0.6979	Remote Similarity	NPC476436
0.6975	Remote Similarity	NPC139373
0.6972	Remote Similarity	NPC254957
0.697	Remote Similarity	NPC134702
0.697	Remote Similarity	NPC471198
0.6968	Remote Similarity	NPC5374
0.6962	Remote Similarity	NPC477397
0.696	Remote Similarity	NPC474366
0.696	Remote Similarity	NPC25961
0.6953	Remote Similarity	NPC118189
0.6952	Remote Similarity	NPC129624
0.6947	Remote Similarity	NPC285192
0.6944	Remote Similarity	NPC284706
0.6942	Remote Similarity	NPC304837
0.6942	Remote Similarity	NPC476258
0.693	Remote Similarity	NPC262725
0.693	Remote Similarity	NPC82541
0.6926	Remote Similarity	NPC471197
0.6908	Remote Similarity	NPC244543
0.6903	Remote Similarity	NPC222561
0.6903	Remote Similarity	NPC308943
0.6901	Remote Similarity	NPC270301
0.6901	Remote Similarity	NPC28368
0.6897	Remote Similarity	NPC87560
0.6897	Remote Similarity	NPC195120
0.6892	Remote Similarity	NPC241263
0.6891	Remote Similarity	NPC223242
0.688	Remote Similarity	NPC76478
0.6878	Remote Similarity	NPC161804
0.6875	Remote Similarity	NPC15987
0.6875	Remote Similarity	NPC288759
0.687	Remote Similarity	NPC30749
0.687	Remote Similarity	NPC469592
0.687	Remote Similarity	NPC268223
0.687	Remote Similarity	NPC471080
0.687	Remote Similarity	NPC114468
0.6867	Remote Similarity	NPC153923
0.686	Remote Similarity	NPC131977
0.6858	Remote Similarity	NPC158551
0.6854	Remote Similarity	NPC39822
0.6849	Remote Similarity	NPC74216
0.6849	Remote Similarity	NPC66777
0.6849	Remote Similarity	NPC471762
0.6847	Remote Similarity	NPC234933
0.6844	Remote Similarity	NPC473460
0.684	Remote Similarity	NPC148391
0.684	Remote Similarity	NPC2905
0.684	Remote Similarity	NPC55470
0.6837	Remote Similarity	NPC97584
0.6835	Remote Similarity	NPC473569
0.6835	Remote Similarity	NPC5630
0.6833	Remote Similarity	NPC476429
0.6826	Remote Similarity	NPC305542
0.6825	Remote Similarity	NPC470548
0.6824	Remote Similarity	NPC469594
0.682	Remote Similarity	NPC14994
0.6815	Remote Similarity	NPC63971
0.6815	Remote Similarity	NPC91868
0.6814	Remote Similarity	NPC301292
0.6814	Remote Similarity	NPC313112
0.681	Remote Similarity	NPC470002
0.681	Remote Similarity	NPC471648
0.681	Remote Similarity	NPC470001
0.6809	Remote Similarity	NPC7560
0.6798	Remote Similarity	NPC330683
0.6798	Remote Similarity	NPC207873
0.6798	Remote Similarity	NPC329567
0.6798	Remote Similarity	NPC100573
0.6796	Remote Similarity	NPC472102
0.6796	Remote Similarity	NPC309531
0.6787	Remote Similarity	NPC165964
0.6783	Remote Similarity	NPC218303
0.6781	Remote Similarity	NPC15384
0.6781	Remote Similarity	NPC313327
0.6781	Remote Similarity	NPC244425
0.678	Remote Similarity	NPC260909
0.6776	Remote Similarity	NPC166169
0.6767	Remote Similarity	NPC176113
0.6766	Remote Similarity	NPC157983
0.6766	Remote Similarity	NPC118154
0.6765	Remote Similarity	NPC266994
0.6762	Remote Similarity	NPC101350
0.6759	Remote Similarity	NPC302235
0.6759	Remote Similarity	NPC258048

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 NPC122886 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	594
0.2-0.3	845
0.3-0.4	1847
0.4-0.5	2894
0.5-0.6	2339
0.6-0.7	422
0.7-0.8	13
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
0.7426	Intermediate Similarity	NPD5186	Approved
0.7426	Intermediate Similarity	NPD5183	Approved
0.7352	Intermediate Similarity	NPD3298	Approved
0.7328	Intermediate Similarity	NPD4981	Phase 2
0.7315	Intermediate Similarity	NPD5071	Phase 2
0.7273	Intermediate Similarity	NPD4465	Phase 2
0.7273	Intermediate Similarity	NPD4467	Phase 2
0.7264	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6795	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3297	Approved
0.7198	Intermediate Similarity	NPD7186	Phase 3
0.7195	Intermediate Similarity	NPD5102	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4082	Approved
0.7124	Intermediate Similarity	NPD4492	Approved
0.7124	Intermediate Similarity	NPD4494	Approved
0.7089	Intermediate Similarity	NPD4373	Phase 2
0.708	Intermediate Similarity	NPD4493	Discontinued
0.7059	Intermediate Similarity	NPD6238	Discontinued
0.7056	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD3437	Discontinued
0.7022	Intermediate Similarity	NPD4022	Approved
0.7022	Intermediate Similarity	NPD3472	Approved
0.7013	Intermediate Similarity	NPD5496	Approved
0.7009	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3940	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7559	Phase 2
0.6966	Remote Similarity	NPD3912	Discontinued
0.6962	Remote Similarity	NPD4952	Phase 3
0.696	Remote Similarity	NPD5860	Discontinued
0.696	Remote Similarity	NPD3372	Discontinued
0.6943	Remote Similarity	NPD4455	Discontinued
0.6933	Remote Similarity	NPD3441	Approved
0.6933	Remote Similarity	NPD3442	Approved
0.693	Remote Similarity	NPD683	Approved
0.6923	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4668	Phase 2
0.692	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6321	Discontinued
0.69	Remote Similarity	NPD3888	Discontinued
0.6898	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2899	Discontinued
0.6861	Remote Similarity	NPD6805	Discontinued
0.686	Remote Similarity	NPD4846	Phase 2
0.6856	Remote Similarity	NPD1945	Phase 1
0.6852	Remote Similarity	NPD3153	Approved
0.6852	Remote Similarity	NPD3154	Approved
0.6838	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7031	Phase 1
0.6828	Remote Similarity	NPD4596	Phase 1
0.682	Remote Similarity	NPD4515	Suspended
0.6818	Remote Similarity	NPD4539	Phase 1
0.6814	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD3893	Discontinued
0.681	Remote Similarity	NPD8149	Discontinued
0.6803	Remote Similarity	NPD7560	Approved
0.6798	Remote Similarity	NPD2906	Approved
0.6798	Remote Similarity	NPD2907	Approved
0.6789	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.678	Remote Similarity	NPD8460	Approved
0.678	Remote Similarity	NPD8459	Approved
0.6776	Remote Similarity	NPD6790	Phase 1
0.677	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD4259	Approved
0.6758	Remote Similarity	NPD4258	Approved
0.6757	Remote Similarity	NPD3964	Approved
0.675	Remote Similarity	NPD6199	Discontinued
0.6741	Remote Similarity	NPD7810	Phase 3
0.6741	Remote Similarity	NPD7811	Phase 3
0.6736	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7627	Approved
0.6726	Remote Similarity	NPD7626	Approved
0.6721	Remote Similarity	NPD4368	Phase 2
0.6711	Remote Similarity	NPD6519	Phase 2
0.67	Remote Similarity	NPD1670	Discontinued
0.6698	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD3479	Discontinued
0.6696	Remote Similarity	NPD7205	Discontinued
0.6692	Remote Similarity	NPD8467	Approved
0.6692	Remote Similarity	NPD8465	Approved
0.6692	Remote Similarity	NPD8466	Approved
0.6667	Remote Similarity	NPD6625	Approved
0.6667	Remote Similarity	NPD5025	Approved
0.6667	Remote Similarity	NPD6644	Discontinued
0.6667	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD6962	Phase 2
0.6652	Remote Similarity	NPD4859	Phase 1
0.6652	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.664	Remote Similarity	NPD7432	Phase 2
0.6624	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3591	Approved
0.6623	Remote Similarity	NPD3592	Approved
0.6622	Remote Similarity	NPD5937	Approved
0.6622	Remote Similarity	NPD5194	Approved
0.6622	Remote Similarity	NPD5196	Approved
0.6622	Remote Similarity	NPD5197	Approved
0.662	Remote Similarity	NPD2246	Approved
0.662	Remote Similarity	NPD2248	Approved
0.662	Remote Similarity	NPD6297	Approved
0.6612	Remote Similarity	NPD7853	Phase 2
0.6609	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7281	Phase 3
0.6606	Remote Similarity	NPD7280	Phase 3
0.6598	Remote Similarity	NPD3259	Approved
0.6595	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD1294	Discontinued
0.6592	Remote Similarity	NPD8425	Approved
0.6592	Remote Similarity	NPD8426	Approved
0.659	Remote Similarity	NPD8363	Approved
0.659	Remote Similarity	NPD8364	Approved
0.6585	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6853	Approved
0.6575	Remote Similarity	NPD6851	Approved
0.6571	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD8429	Approved
0.6566	Remote Similarity	NPD8427	Approved
0.6566	Remote Similarity	NPD8428	Approved
0.6565	Remote Similarity	NPD4130	Phase 3
0.6565	Remote Similarity	NPD3507	Phase 2
0.6557	Remote Similarity	NPD4885	Approved
0.6553	Remote Similarity	NPD5293	Phase 2
0.6553	Remote Similarity	NPD4679	Discontinued
0.6546	Remote Similarity	NPD6716	Phase 1
0.6544	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD5445	Approved
0.654	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7225	Discontinued
0.6538	Remote Similarity	NPD7301	Phase 3
0.6538	Remote Similarity	NPD7605	Discovery
0.6533	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD3793	Phase 3
0.6528	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7048	Phase 3
0.6516	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5637	Discontinued
0.6512	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.651	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.651	Remote Similarity	NPD8463	Approved
0.6505	Remote Similarity	NPD814	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8311	Discontinued
0.6498	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD8461	Discontinued
0.6498	Remote Similarity	NPD8091	Phase 3
0.6491	Remote Similarity	NPD4496	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5457	Discontinued
0.6489	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD7803	Approved
0.6473	Remote Similarity	NPD7279	Phase 2
0.6473	Remote Similarity	NPD7278	Phase 2
0.6473	Remote Similarity	NPD7570	Approved
0.6473	Remote Similarity	NPD7569	Approved
0.6471	Remote Similarity	NPD5632	Approved
0.6468	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD3416	Discontinued
0.646	Remote Similarity	NPD5582	Discontinued
0.6455	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6982	Phase 2
0.6447	Remote Similarity	NPD6874	Approved
0.6447	Remote Similarity	NPD1880	Phase 3
0.6445	Remote Similarity	NPD5532	Phase 2
0.6444	Remote Similarity	NPD4466	Phase 1
0.6444	Remote Similarity	NPD5610	Approved
0.6438	Remote Similarity	NPD8027	Approved
0.6435	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD7316	Discontinued
0.6429	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD6557	Phase 2
0.6425	Remote Similarity	NPD6618	Phase 2
0.6422	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD1307	Phase 2
0.6415	Remote Similarity	NPD1309	Phase 2
0.6414	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD6517	Phase 3
0.6411	Remote Similarity	NPD3006	Discontinued
0.6408	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5022	Discontinued
0.6407	Remote Similarity	NPD3802	Phase 3
0.6405	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD2247	Approved
0.6402	Remote Similarity	NPD2249	Approved
0.6402	Remote Similarity	NPD2681	Approved
0.6402	Remote Similarity	NPD2680	Approved
0.64	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD7922	Phase 1
0.6395	Remote Similarity	NPD8255	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