NPASS Compound

Structure

CID118776 OpenBabel06191715472D 27 29 0 0 0 0 0 0 0 0999 V2000 -4.3301 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 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 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 26 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 16 2 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 20 2 0 0 0 0 13 21 2 0 0 0 0 14 15 1 0 0 0 0 14 17 2 0 0 0 0 15 27 1 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 19 23 1 0 0 0 0 19 24 2 0 0 0 0 20 22 1 0 0 0 0 20 26 1 0 0 0 0 21 23 1 0 0 0 0 21 27 1 0 0 0 0 22 24 1 0 0 0 0 23 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.2
Volume:	396.541
LogP:	5.452
LogD:	4.494
LogS:	-5.423
# Rotatable Bonds:	7
TPSA:	44.24
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.39
Synthetic Accessibility Score:	2.57
Fsp3:	0.304
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.852
MDCK Permeability:	1.8465263565303758e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.089
30% Bioavailability (F30%):	0.165

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	97.14929962158203%
Volume Distribution (VD):	0.645
Pgp-substrate:	0.8947847485542297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.816
CYP2C19-inhibitor:	0.885
CYP2C19-substrate:	0.263
CYP2C9-inhibitor:	0.917
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.479
CYP2D6-substrate:	0.877
CYP3A4-inhibitor:	0.706
CYP3A4-substrate:	0.308

ADMET: Excretion

Clearance (CL):	6.117
Half-life (T1/2):	0.19

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.511
Drug-inuced Liver Injury (DILI):	0.401
AMES Toxicity:	0.298
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.048
Skin Sensitization:	0.688
Carcinogencity:	0.074
Eye Corrosion:	0.003
Eye Irritation:	0.254
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC118776

Natural Product ID:	NPC118776
*Common Name:**	Phenaziterpene B
IUPAC Name:	1-[(2E)-3,7-dimethylocta-2,6-dienoxy]-6-methoxyphenazine
Synonyms:
Standard InCHIKey:	AYBXOQNDOSRELU-SAPNQHFASA-N
Standard InCHI:	InChI=1S/C23H26N2O2/c1-16(2)8-5-9-17(3)14-15-27-21-13-7-11-19-23(21)25-18-10-6-12-20(26-4)22(18)24-19/h6-8,10-14H,5,9,15H2,1-4H3/b17-14+
SMILES:	COc1cccc2c1nc1cccc(c1n2)OC/C=C(/CCC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3092701
PubChem CID:	73056209
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000486] Quinoxalines [CHEMONTID:0000416] Phenazines 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
NPO6655.3	Streptomyces niveus SCSIO 3406	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24251399]

☑ 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	4
MIC	7

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	100000.0	nM	PMID[513170]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	52700.0	nM	PMID[513170]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	30400.0	nM	PMID[513170]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	21900.0	nM	PMID[513170]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[513170]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	128.0	ug.mL-1	PMID[513170]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	128.0	ug.mL-1	PMID[513170]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	128.0	ug.mL-1	PMID[513170]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	128.0	ug.mL-1	PMID[513170]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128.0	ug.mL-1	PMID[513170]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	128.0	ug.mL-1	PMID[513170]

☑ 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 NPC118776 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	662
0.1-0.2	8708
0.2-0.3	9138
0.3-0.4	13608
0.4-0.5	7418
0.5-0.6	2339
0.6-0.7	729
0.7-0.8	83
0.8-0.85	7
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9641	High Similarity	NPC110741
0.9441	High Similarity	NPC1527
0.8833	High Similarity	NPC470586
0.878	High Similarity	NPC285635
0.8548	High Similarity	NPC308392
0.8541	High Similarity	NPC471736
0.8529	High Similarity	NPC258773
0.8503	High Similarity	NPC79911
0.8443	Intermediate Similarity	NPC120798
0.8212	Intermediate Similarity	NPC314573
0.8114	Intermediate Similarity	NPC95898
0.7929	Intermediate Similarity	NPC36168
0.7816	Intermediate Similarity	NPC118511
0.7791	Intermediate Similarity	NPC26850
0.7663	Intermediate Similarity	NPC42591
0.7637	Intermediate Similarity	NPC478023
0.7624	Intermediate Similarity	NPC283152
0.7616	Intermediate Similarity	NPC26872
0.7568	Intermediate Similarity	NPC20249
0.7559	Intermediate Similarity	NPC124300
0.7539	Intermediate Similarity	NPC267928
0.7538	Intermediate Similarity	NPC470930
0.7523	Intermediate Similarity	NPC291609
0.75	Intermediate Similarity	NPC219963
0.7458	Intermediate Similarity	NPC177404
0.7454	Intermediate Similarity	NPC310618
0.745	Intermediate Similarity	NPC26679
0.7444	Intermediate Similarity	NPC476518
0.7405	Intermediate Similarity	NPC161887
0.7405	Intermediate Similarity	NPC266551
0.7403	Intermediate Similarity	NPC14651
0.7403	Intermediate Similarity	NPC121658
0.7398	Intermediate Similarity	NPC476138
0.7398	Intermediate Similarity	NPC245816
0.7382	Intermediate Similarity	NPC226202
0.7377	Intermediate Similarity	NPC288943
0.7371	Intermediate Similarity	NPC18487
0.7333	Intermediate Similarity	NPC19872
0.7333	Intermediate Similarity	NPC315957
0.7327	Intermediate Similarity	NPC476287
0.7326	Intermediate Similarity	NPC62069
0.7322	Intermediate Similarity	NPC312872
0.732	Intermediate Similarity	NPC72211
0.73	Intermediate Similarity	NPC185782
0.7297	Intermediate Similarity	NPC472168
0.7268	Intermediate Similarity	NPC111624
0.7268	Intermediate Similarity	NPC197141
0.7264	Intermediate Similarity	NPC469554
0.7264	Intermediate Similarity	NPC219664
0.7263	Intermediate Similarity	NPC242928
0.7259	Intermediate Similarity	NPC66815
0.725	Intermediate Similarity	NPC287208
0.7222	Intermediate Similarity	NPC223427
0.7219	Intermediate Similarity	NPC474798
0.7216	Intermediate Similarity	NPC70259
0.7214	Intermediate Similarity	NPC209769
0.7214	Intermediate Similarity	NPC469589
0.7211	Intermediate Similarity	NPC66083
0.7208	Intermediate Similarity	NPC232727
0.7202	Intermediate Similarity	NPC475190
0.7202	Intermediate Similarity	NPC84853
0.7194	Intermediate Similarity	NPC128823
0.7192	Intermediate Similarity	NPC203168
0.7189	Intermediate Similarity	NPC473432
0.7178	Intermediate Similarity	NPC167860
0.7178	Intermediate Similarity	NPC123976
0.7166	Intermediate Similarity	NPC478032
0.7165	Intermediate Similarity	NPC205934
0.7165	Intermediate Similarity	NPC43787
0.7158	Intermediate Similarity	NPC204385
0.7157	Intermediate Similarity	NPC11017
0.7157	Intermediate Similarity	NPC250448
0.715	Intermediate Similarity	NPC473179
0.7136	Intermediate Similarity	NPC162484
0.7136	Intermediate Similarity	NPC475774
0.7129	Intermediate Similarity	NPC174758
0.7129	Intermediate Similarity	NPC174672
0.7123	Intermediate Similarity	NPC314954
0.7113	Intermediate Similarity	NPC79293
0.7113	Intermediate Similarity	NPC279401
0.7103	Intermediate Similarity	NPC101543
0.7092	Intermediate Similarity	NPC474188
0.7087	Intermediate Similarity	NPC8022
0.7087	Intermediate Similarity	NPC470799
0.7085	Intermediate Similarity	NPC291535
0.7085	Intermediate Similarity	NPC475085
0.7085	Intermediate Similarity	NPC475112
0.7079	Intermediate Similarity	NPC470931
0.7073	Intermediate Similarity	NPC469592
0.7073	Intermediate Similarity	NPC471080
0.7071	Intermediate Similarity	NPC329747
0.7067	Intermediate Similarity	NPC17565
0.7065	Intermediate Similarity	NPC476106
0.7056	Intermediate Similarity	NPC475253
0.7053	Intermediate Similarity	NPC320394
0.7053	Intermediate Similarity	NPC84478
0.7052	Intermediate Similarity	NPC470403
0.7052	Intermediate Similarity	NPC470404
0.7052	Intermediate Similarity	NPC470394
0.7035	Intermediate Similarity	NPC476044
0.7035	Intermediate Similarity	NPC267423
0.7024	Intermediate Similarity	NPC94157
0.7024	Intermediate Similarity	NPC264176
0.702	Intermediate Similarity	NPC187558
0.7018	Intermediate Similarity	NPC30540
0.7015	Intermediate Similarity	NPC285558
0.7014	Intermediate Similarity	NPC65277
0.701	Intermediate Similarity	NPC199667
0.7005	Intermediate Similarity	NPC70956
0.7005	Intermediate Similarity	NPC194724
0.7005	Intermediate Similarity	NPC243834
0.6991	Remote Similarity	NPC329631
0.6986	Remote Similarity	NPC193267
0.6986	Remote Similarity	NPC213530
0.6984	Remote Similarity	NPC168486
0.6984	Remote Similarity	NPC222592
0.698	Remote Similarity	NPC472111
0.6974	Remote Similarity	NPC141915
0.6974	Remote Similarity	NPC280964
0.6974	Remote Similarity	NPC114335
0.6971	Remote Similarity	NPC470395
0.6961	Remote Similarity	NPC473181
0.6948	Remote Similarity	NPC200888
0.6947	Remote Similarity	NPC206201
0.6943	Remote Similarity	NPC206251
0.6943	Remote Similarity	NPC74382
0.6942	Remote Similarity	NPC473180
0.6938	Remote Similarity	NPC469594
0.6931	Remote Similarity	NPC164374
0.6931	Remote Similarity	NPC137929
0.6923	Remote Similarity	NPC469390
0.6923	Remote Similarity	NPC274982
0.6916	Remote Similarity	NPC187145
0.6916	Remote Similarity	NPC473185
0.6915	Remote Similarity	NPC295898
0.6912	Remote Similarity	NPC475910
0.6908	Remote Similarity	NPC162530
0.6905	Remote Similarity	NPC208084
0.6904	Remote Similarity	NPC131017
0.69	Remote Similarity	NPC176538
0.6897	Remote Similarity	NPC304183
0.6891	Remote Similarity	NPC61350
0.6888	Remote Similarity	NPC133140
0.6888	Remote Similarity	NPC195268
0.6882	Remote Similarity	NPC477888
0.6878	Remote Similarity	NPC201697
0.6872	Remote Similarity	NPC153769
0.6872	Remote Similarity	NPC132642
0.6872	Remote Similarity	NPC134079
0.6854	Remote Similarity	NPC288445
0.6847	Remote Similarity	NPC36229
0.6847	Remote Similarity	NPC16452
0.6847	Remote Similarity	NPC476581
0.6842	Remote Similarity	NPC152768
0.6842	Remote Similarity	NPC148183
0.684	Remote Similarity	NPC310118
0.6831	Remote Similarity	NPC25899
0.6829	Remote Similarity	NPC82548
0.6825	Remote Similarity	NPC292958
0.6821	Remote Similarity	NPC224327
0.6816	Remote Similarity	NPC121772
0.6812	Remote Similarity	NPC146418
0.6798	Remote Similarity	NPC469440
0.6795	Remote Similarity	NPC227824
0.6792	Remote Similarity	NPC128115
0.6792	Remote Similarity	NPC86078
0.6779	Remote Similarity	NPC472098
0.6779	Remote Similarity	NPC48353
0.6778	Remote Similarity	NPC284348
0.6777	Remote Similarity	NPC131885
0.6766	Remote Similarity	NPC4071
0.6766	Remote Similarity	NPC476578
0.6766	Remote Similarity	NPC476582
0.6759	Remote Similarity	NPC110151
0.6758	Remote Similarity	NPC473182
0.6758	Remote Similarity	NPC141053
0.6743	Remote Similarity	NPC260434
0.6742	Remote Similarity	NPC161292
0.6738	Remote Similarity	NPC44161
0.6736	Remote Similarity	NPC176127
0.6731	Remote Similarity	NPC187501
0.673	Remote Similarity	NPC305984
0.673	Remote Similarity	NPC473513
0.6721	Remote Similarity	NPC116573
0.6714	Remote Similarity	NPC477533
0.6704	Remote Similarity	NPC257142
0.6703	Remote Similarity	NPC48192
0.6702	Remote Similarity	NPC211997
0.6701	Remote Similarity	NPC284559
0.67	Remote Similarity	NPC31930
0.6699	Remote Similarity	NPC193777
0.6698	Remote Similarity	NPC173080
0.6683	Remote Similarity	NPC476167
0.6683	Remote Similarity	NPC198673
0.6683	Remote Similarity	NPC290689
0.6683	Remote Similarity	NPC5145
0.6683	Remote Similarity	NPC230403
0.6682	Remote Similarity	NPC198503
0.6682	Remote Similarity	NPC477532
0.6682	Remote Similarity	NPC60621

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 NPC118776 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	906
0.2-0.3	760
0.3-0.4	1963
0.4-0.5	2926
0.5-0.6	1653
0.6-0.7	540
0.7-0.8	48
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
0.8	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7796	Intermediate Similarity	NPD4372	Phase 1
0.7676	Intermediate Similarity	NPD6393	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD1622	Discontinued
0.7527	Intermediate Similarity	NPD5256	Discontinued
0.7526	Intermediate Similarity	NPD6590	Discontinued
0.75	Intermediate Similarity	NPD4204	Approved
0.75	Intermediate Similarity	NPD4203	Approved
0.7487	Intermediate Similarity	NPD6550	Discontinued
0.7413	Intermediate Similarity	NPD2314	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD2772	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD5530	Phase 1
0.7396	Intermediate Similarity	NPD3477	Phase 2
0.7396	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7284	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD5930	Phase 3
0.7358	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD565	Phase 2
0.7333	Intermediate Similarity	NPD1739	Approved
0.7333	Intermediate Similarity	NPD1740	Approved
0.733	Intermediate Similarity	NPD6569	Phase 2
0.7323	Intermediate Similarity	NPD3003	Approved
0.7306	Intermediate Similarity	NPD5512	Phase 3
0.7306	Intermediate Similarity	NPD774	Phase 3
0.7304	Intermediate Similarity	NPD1744	Approved
0.7302	Intermediate Similarity	NPD1034	Phase 3
0.7302	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3920	Phase 2
0.7286	Intermediate Similarity	NPD7222	Phase 2
0.7273	Intermediate Similarity	NPD4795	Phase 2
0.7268	Intermediate Similarity	NPD6988	Phase 1
0.7233	Intermediate Similarity	NPD7194	Discontinued
0.7228	Intermediate Similarity	NPD4131	Phase 3
0.7206	Intermediate Similarity	NPD5903	Approved
0.7206	Intermediate Similarity	NPD5902	Approved
0.7194	Intermediate Similarity	NPD1768	Approved
0.719	Intermediate Similarity	NPD1603	Discontinued
0.7189	Intermediate Similarity	NPD4354	Approved
0.7165	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD5658	Approved
0.7143	Intermediate Similarity	NPD3939	Suspended
0.7143	Intermediate Similarity	NPD4502	Phase 2
0.7119	Intermediate Similarity	NPD789	Phase 2
0.7116	Intermediate Similarity	NPD3838	Phase 3
0.7114	Intermediate Similarity	NPD7453	Approved
0.7114	Intermediate Similarity	NPD7452	Approved
0.7108	Intermediate Similarity	NPD4927	Discontinued
0.7095	Intermediate Similarity	NPD6306	Phase 2
0.7087	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD8117	Approved
0.7078	Intermediate Similarity	NPD8116	Phase 3
0.7077	Intermediate Similarity	NPD6251	Discontinued
0.7067	Intermediate Similarity	NPD3875	Discontinued
0.7065	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7468	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2540	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6060	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5429	Discontinued
0.7028	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD7674	Phase 3
0.7028	Intermediate Similarity	NPD7426	Phase 1
0.7028	Intermediate Similarity	NPD7675	Phase 3
0.702	Intermediate Similarity	NPD5547	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4548	Discontinued
0.7019	Intermediate Similarity	NPD6985	Discontinued
0.7019	Intermediate Similarity	NPD5632	Approved
0.7016	Intermediate Similarity	NPD4889	Approved
0.7015	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4498	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6643	Discontinued
0.6995	Remote Similarity	NPD7467	Discontinued
0.6991	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.699	Remote Similarity	NPD3945	Discontinued
0.699	Remote Similarity	NPD1602	Discontinued
0.6986	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD5416	Discontinued
0.6976	Remote Similarity	NPD3570	Phase 2
0.6968	Remote Similarity	NPD4071	Approved
0.6968	Remote Similarity	NPD4072	Approved
0.6959	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1392	Approved
0.6942	Remote Similarity	NPD6202	Discontinued
0.6923	Remote Similarity	NPD4148	Approved
0.6923	Remote Similarity	NPD1418	Phase 2
0.692	Remote Similarity	NPD8324	Phase 2
0.6919	Remote Similarity	NPD4673	Phase 2
0.6919	Remote Similarity	NPD2476	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD9574	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD4418	Discontinued
0.6901	Remote Similarity	NPD6246	Approved
0.6897	Remote Similarity	NPD6150	Discontinued
0.6893	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6572	Phase 2
0.6892	Remote Similarity	NPD7067	Approved
0.6892	Remote Similarity	NPD6573	Phase 3
0.6892	Remote Similarity	NPD7068	Approved
0.6889	Remote Similarity	NPD5482	Discontinued
0.6888	Remote Similarity	NPD3922	Approved
0.6888	Remote Similarity	NPD3923	Approved
0.6888	Remote Similarity	NPD3921	Approved
0.6888	Remote Similarity	NPD3924	Approved
0.6878	Remote Similarity	NPD6159	Phase 2
0.6872	Remote Similarity	NPD2410	Phase 2
0.6852	Remote Similarity	NPD5479	Discontinued
0.6847	Remote Similarity	NPD3397	Phase 2
0.6845	Remote Similarity	NPD5420	Discontinued
0.6845	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.684	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD2952	Discontinued
0.6832	Remote Similarity	NPD6208	Discontinued
0.6828	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4021	Phase 2
0.6818	Remote Similarity	NPD3396	Approved
0.6818	Remote Similarity	NPD3395	Approved
0.6816	Remote Similarity	NPD7413	Phase 3
0.6816	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6245	Phase 2
0.6814	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2581	Approved
0.6813	Remote Similarity	NPD2582	Approved
0.6809	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD1856	Discontinued
0.6808	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD3503	Approved
0.6789	Remote Similarity	NPD3504	Approved
0.6788	Remote Similarity	NPD1334	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD5999	Phase 2
0.6761	Remote Similarity	NPD7726	Phase 1
0.6758	Remote Similarity	NPD6494	Phase 2
0.6758	Remote Similarity	NPD7558	Phase 2
0.6758	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4858	Phase 2
0.6754	Remote Similarity	NPD6742	Phase 2
0.6754	Remote Similarity	NPD6743	Phase 2
0.6753	Remote Similarity	NPD6227	Discontinued
0.6749	Remote Similarity	NPD1897	Discontinued
0.6742	Remote Similarity	NPD4368	Phase 2
0.6739	Remote Similarity	NPD112	Approved
0.6739	Remote Similarity	NPD9705	Discontinued
0.6731	Remote Similarity	NPD6220	Phase 3
0.6727	Remote Similarity	NPD2951	Discontinued
0.672	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD2599	Approved
0.6719	Remote Similarity	NPD2601	Approved
0.6719	Remote Similarity	NPD2600	Approved
0.6718	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD4921	Phase 3
0.6718	Remote Similarity	NPD4919	Phase 3
0.6716	Remote Similarity	NPD772	Phase 3
0.6713	Remote Similarity	NPD5640	Discontinued
0.6702	Remote Similarity	NPD5320	Approved
0.6702	Remote Similarity	NPD5319	Approved
0.6701	Remote Similarity	NPD7877	Suspended
0.6699	Remote Similarity	NPD6290	Phase 2
0.6699	Remote Similarity	NPD7069	Discontinued
0.6698	Remote Similarity	NPD4429	Discontinued
0.6698	Remote Similarity	NPD7395	Discontinued
0.6697	Remote Similarity	NPD5022	Discontinued
0.6697	Remote Similarity	NPD8512	Phase 3
0.6685	Remote Similarity	NPD9595	Approved
0.6685	Remote Similarity	NPD9596	Approved
0.6684	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3386	Phase 2
0.6684	Remote Similarity	NPD5938	Phase 3
0.6683	Remote Similarity	NPD2958	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD8510	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD2472	Approved
0.6682	Remote Similarity	NPD2471	Approved
0.6682	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5944	Phase 1
0.6667	Remote Similarity	NPD6366	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5802	Phase 2
0.6667	Remote Similarity	NPD4996	Approved
0.6667	Remote Similarity	NPD3370	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1941	Approved
0.6667	Remote Similarity	NPD2334	Discontinued
0.6667	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4995	Approved
0.6667	Remote Similarity	NPD204	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5945	Phase 1
0.6652	Remote Similarity	NPD5877	Phase 3
0.6652	Remote Similarity	NPD6760	Discontinued
0.6652	Remote Similarity	NPD5876	Phase 3
0.6651	Remote Similarity	NPD3440	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD5066	Phase 2
0.6651	Remote Similarity	NPD5067	Phase 2
0.6651	Remote Similarity	NPD5559	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