NPASS Compound

Structure

NPC473569 OpenBabel07101719242D 24 29 0 0 1 0 0 0 0 0999 V2000 -3.8099 0.8148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6538 -0.5647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0194 1.5295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2567 1.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9456 1.7518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3310 1.5145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3082 -0.4278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3523 0.8383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1388 -0.1385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3271 0.9061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3832 0.2085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0827 0.6854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1421 1.8968 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5573 1.4199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.6473 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6205 0.5758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1510 0.5299 0.0000 N 0 0 3 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 -0.0933 -1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9836 0.2515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 7 2 0 0 0 0 2 9 1 0 0 0 0 3 4 2 0 0 0 0 3 13 1 0 0 0 0 4 15 1 0 0 0 0 5 8 1 0 0 0 0 5 16 1 0 0 0 0 6 10 1 0 0 0 0 7 19 1 0 0 0 0 8 19 1 0 0 0 0 9 21 1 0 0 0 0 10 21 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 24 1 0 0 0 0 14 6 1 6 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 16 20 1 1 0 0 0 17 22 1 0 0 0 0 18 22 1 0 0 0 0 18 23 2 0 0 0 0 19 20 1 1 0 0 0 20 21 1 6 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.17
Volume:	329.529
LogP:	3.54
LogD:	2.223
LogS:	-4.424
# Rotatable Bonds:	1
TPSA:	32.78
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.745
Synthetic Accessibility Score:	5.622
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.88
MDCK Permeability:	1.905200224427972e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.967
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.524
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.997
Plasma Protein Binding (PPB):	71.24500274658203%
Volume Distribution (VD):	1.749
Pgp-substrate:	27.312040328979492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.766
CYP2C19-inhibitor:	0.771
CYP2C19-substrate:	0.945
CYP2C9-inhibitor:	0.597
CYP2C9-substrate:	0.662
CYP2D6-inhibitor:	0.343
CYP2D6-substrate:	0.647
CYP3A4-inhibitor:	0.954
CYP3A4-substrate:	0.949

ADMET: Excretion

Clearance (CL):	8.758
Half-life (T1/2):	0.153

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.289
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.918
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.327
Carcinogencity:	0.964
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.69

Download Data

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

Natural Product: NPC473569

Natural Product ID:	NPC473569
*Common Name:**	Isoschizogaline
IUPAC Name:	n.a.
Synonyms:	Isoschizogaline
Standard InCHIKey:	GHZIYRPRBMQWSP-ZXUOCUECSA-N
Standard InCHI:	InChI=1S/C20H22N2O2/c1-24-13-3-4-15-14-6-10-21-9-2-7-19-8-5-16(14)20(19,21)22(17(15)11-13)18(23)12-19/h2-4,7,11,14,16H,5-6,8-10,12H2,1H3/t14-,16+,19-,20-/m0/s1
SMILES:	COc1ccc2c(c1)N1C(=O)C[C@]34[C@@]51[C@@H]([C@H]2CCN5CC=C3)CC4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445975
PubChem CID:	636755
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000053] Aminoquinolines 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
NPO32657	schizozygia coffaeoides	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975502]

☑ 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
MIC	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	500.0	ug.mL-1	PMID[490396]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	>	500.0	ug.mL-1	PMID[490396]
NPT328	Organism	Epidermophyton floccosum	Epidermophyton floccosum	MIC	>	500.0	ug.mL-1	PMID[490396]
NPT3651	Organism	Trichophyton tonsurans	Trichophyton tonsurans	MIC	>	500.0	ug.mL-1	PMID[490396]
NPT4353	Organism	Trichophyton interdigitale	Trichophyton interdigitale	MIC	>	500.0	ug.mL-1	PMID[490396]
NPT487	Organism	Cladosporium cladosporioides	Cladosporium cladosporioides	MIC	>	500.0	ug.mL-1	PMID[490396]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	MIC	>	500.0	ug.mL-1	PMID[490396]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	500.0	ug.mL-1	PMID[490396]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	500.0	ug.mL-1	PMID[490396]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	125.0	ug.mL-1	PMID[490396]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	62.5	ug.mL-1	PMID[490396]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	500.0	ug.mL-1	PMID[490396]

☑ 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 NPC473569 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	393
0.1-0.2	1770
0.2-0.3	7886
0.3-0.4	9518
0.4-0.5	17174
0.5-0.6	4909
0.6-0.7	941
0.7-0.8	102
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.837	Intermediate Similarity	NPC473004
0.8299	Intermediate Similarity	NPC82541
0.8254	Intermediate Similarity	NPC67904
0.8245	Intermediate Similarity	NPC100863
0.8242	Intermediate Similarity	NPC473007
0.8214	Intermediate Similarity	NPC473006
0.8182	Intermediate Similarity	NPC230313
0.8065	Intermediate Similarity	NPC473008
0.7989	Intermediate Similarity	NPC243626
0.7926	Intermediate Similarity	NPC22476
0.7887	Intermediate Similarity	NPC473005
0.7861	Intermediate Similarity	NPC21425
0.7784	Intermediate Similarity	NPC127178
0.7784	Intermediate Similarity	NPC138830
0.7766	Intermediate Similarity	NPC477161
0.7711	Intermediate Similarity	NPC159815
0.7696	Intermediate Similarity	NPC204970
0.765	Intermediate Similarity	NPC477160
0.7585	Intermediate Similarity	NPC46259
0.7542	Intermediate Similarity	NPC471122
0.7538	Intermediate Similarity	NPC14339
0.75	Intermediate Similarity	NPC174629
0.7488	Intermediate Similarity	NPC219397
0.7473	Intermediate Similarity	NPC299582
0.7473	Intermediate Similarity	NPC471124
0.7461	Intermediate Similarity	NPC203628
0.7452	Intermediate Similarity	NPC10653
0.7452	Intermediate Similarity	NPC318525
0.7451	Intermediate Similarity	NPC10732
0.745	Intermediate Similarity	NPC87714
0.745	Intermediate Similarity	NPC475147
0.7366	Intermediate Similarity	NPC264176
0.7363	Intermediate Similarity	NPC315498
0.7363	Intermediate Similarity	NPC230942
0.734	Intermediate Similarity	NPC205926
0.731	Intermediate Similarity	NPC303214
0.7308	Intermediate Similarity	NPC305984
0.7304	Intermediate Similarity	NPC475133
0.7273	Intermediate Similarity	NPC77777
0.7273	Intermediate Similarity	NPC161804
0.7263	Intermediate Similarity	NPC39822
0.7238	Intermediate Similarity	NPC29285
0.7238	Intermediate Similarity	NPC37957
0.7236	Intermediate Similarity	NPC71124
0.7231	Intermediate Similarity	NPC474059
0.7228	Intermediate Similarity	NPC41216
0.7225	Intermediate Similarity	NPC126556
0.7222	Intermediate Similarity	NPC478076
0.7219	Intermediate Similarity	NPC85482
0.7214	Intermediate Similarity	NPC232600
0.7198	Intermediate Similarity	NPC127996
0.7198	Intermediate Similarity	NPC113946
0.7198	Intermediate Similarity	NPC119722
0.7194	Intermediate Similarity	NPC1820
0.7194	Intermediate Similarity	NPC28510
0.7191	Intermediate Similarity	NPC242000
0.7184	Intermediate Similarity	NPC476651
0.7179	Intermediate Similarity	NPC477186
0.7158	Intermediate Similarity	NPC301163
0.7151	Intermediate Similarity	NPC471123
0.7129	Intermediate Similarity	NPC189661
0.7116	Intermediate Similarity	NPC476436
0.7115	Intermediate Similarity	NPC470482
0.7115	Intermediate Similarity	NPC470481
0.7114	Intermediate Similarity	NPC5374
0.7104	Intermediate Similarity	NPC469428
0.7102	Intermediate Similarity	NPC308197
0.7101	Intermediate Similarity	NPC269449
0.7097	Intermediate Similarity	NPC472106
0.7094	Intermediate Similarity	NPC295898
0.709	Intermediate Similarity	NPC214626
0.709	Intermediate Similarity	NPC251212
0.709	Intermediate Similarity	NPC139085
0.7081	Intermediate Similarity	NPC472120
0.7081	Intermediate Similarity	NPC472101
0.7081	Intermediate Similarity	NPC472117
0.7075	Intermediate Similarity	NPC153923
0.707	Intermediate Similarity	NPC115588
0.7059	Intermediate Similarity	NPC279527
0.7059	Intermediate Similarity	NPC214960
0.7059	Intermediate Similarity	NPC207971
0.7056	Intermediate Similarity	NPC250960
0.7056	Intermediate Similarity	NPC71539
0.7056	Intermediate Similarity	NPC473329
0.7039	Intermediate Similarity	NPC478075
0.7035	Intermediate Similarity	NPC254957
0.7028	Intermediate Similarity	NPC303658
0.7028	Intermediate Similarity	NPC473041
0.7024	Intermediate Similarity	NPC268077
0.7005	Intermediate Similarity	NPC70172
0.7005	Intermediate Similarity	NPC24954
0.7	Intermediate Similarity	NPC476425
0.6995	Remote Similarity	NPC288110
0.6995	Remote Similarity	NPC85613
0.6995	Remote Similarity	NPC70092
0.6991	Remote Similarity	NPC21638
0.6989	Remote Similarity	NPC176983
0.698	Remote Similarity	NPC234933
0.6972	Remote Similarity	NPC471762
0.6972	Remote Similarity	NPC74216
0.6971	Remote Similarity	NPC469560
0.697	Remote Similarity	NPC105055
0.697	Remote Similarity	NPC22689
0.697	Remote Similarity	NPC5630
0.6968	Remote Similarity	NPC472114
0.6968	Remote Similarity	NPC472115
0.6959	Remote Similarity	NPC266994
0.6955	Remote Similarity	NPC476429
0.6952	Remote Similarity	NPC472098
0.695	Remote Similarity	NPC203972
0.695	Remote Similarity	NPC470485
0.6939	Remote Similarity	NPC102760
0.6935	Remote Similarity	NPC93653
0.6927	Remote Similarity	NPC476441
0.6912	Remote Similarity	NPC231924
0.6911	Remote Similarity	NPC307640
0.6908	Remote Similarity	NPC195787
0.6908	Remote Similarity	NPC246140
0.6907	Remote Similarity	NPC5167
0.6901	Remote Similarity	NPC195636
0.6897	Remote Similarity	NPC23080
0.6897	Remote Similarity	NPC193906
0.6895	Remote Similarity	NPC469915
0.6891	Remote Similarity	NPC127082
0.6891	Remote Similarity	NPC260075
0.689	Remote Similarity	NPC174758
0.6866	Remote Similarity	NPC471825
0.6859	Remote Similarity	NPC471604
0.6854	Remote Similarity	NPC152768
0.6854	Remote Similarity	NPC470002
0.6854	Remote Similarity	NPC470001
0.6854	Remote Similarity	NPC148183
0.6854	Remote Similarity	NPC234772
0.6853	Remote Similarity	NPC259626
0.685	Remote Similarity	NPC470483
0.6845	Remote Similarity	NPC52801
0.6842	Remote Similarity	NPC33507
0.6837	Remote Similarity	NPC222046
0.6835	Remote Similarity	NPC122886
0.6823	Remote Similarity	NPC285622
0.6823	Remote Similarity	NPC96901
0.6823	Remote Similarity	NPC73280
0.6818	Remote Similarity	NPC66777
0.6816	Remote Similarity	NPC114039
0.6816	Remote Similarity	NPC206109
0.6811	Remote Similarity	NPC161827
0.6809	Remote Similarity	NPC286871
0.6806	Remote Similarity	NPC476069
0.6804	Remote Similarity	NPC285941
0.6802	Remote Similarity	NPC2933
0.68	Remote Similarity	NPC45389
0.6794	Remote Similarity	NPC198160
0.6779	Remote Similarity	NPC470484
0.6774	Remote Similarity	NPC128476
0.6773	Remote Similarity	NPC473458
0.6771	Remote Similarity	NPC473105
0.6769	Remote Similarity	NPC287152
0.6769	Remote Similarity	NPC321211
0.6765	Remote Similarity	NPC272706
0.6763	Remote Similarity	NPC15987
0.6762	Remote Similarity	NPC475910
0.6756	Remote Similarity	NPC184680
0.6755	Remote Similarity	NPC472102
0.6755	Remote Similarity	NPC309531
0.6755	Remote Similarity	NPC225319
0.6751	Remote Similarity	NPC256288
0.6751	Remote Similarity	NPC98197
0.6749	Remote Similarity	NPC198401
0.6748	Remote Similarity	NPC329747
0.6742	Remote Similarity	NPC194740
0.6742	Remote Similarity	NPC311906
0.6739	Remote Similarity	NPC66936
0.6736	Remote Similarity	NPC477185
0.6735	Remote Similarity	NPC287588
0.6734	Remote Similarity	NPC116007
0.6733	Remote Similarity	NPC79213
0.6732	Remote Similarity	NPC17677
0.673	Remote Similarity	NPC469589
0.6726	Remote Similarity	NPC474183
0.6726	Remote Similarity	NPC151171
0.6726	Remote Similarity	NPC470784
0.6726	Remote Similarity	NPC470785
0.6725	Remote Similarity	NPC250476
0.6718	Remote Similarity	NPC476326
0.6718	Remote Similarity	NPC477187
0.6717	Remote Similarity	NPC179704
0.6717	Remote Similarity	NPC84478
0.6715	Remote Similarity	NPC471489
0.6714	Remote Similarity	NPC308943
0.6712	Remote Similarity	NPC470821
0.6702	Remote Similarity	NPC243673
0.6702	Remote Similarity	NPC193410
0.6702	Remote Similarity	NPC63210
0.6702	Remote Similarity	NPC310403
0.6702	Remote Similarity	NPC263709
0.6702	Remote Similarity	NPC148468
0.6702	Remote Similarity	NPC97380
0.6701	Remote Similarity	NPC470548
0.6699	Remote Similarity	NPC285558
0.6699	Remote Similarity	NPC241263

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 NPC473569 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	600
0.2-0.3	778
0.3-0.4	1330
0.4-0.5	3292
0.5-0.6	2569
0.6-0.7	321
0.7-0.8	21
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
0.7717	Intermediate Similarity	NPD5600	Discontinued
0.7582	Intermediate Similarity	NPD6457	Approved
0.7541	Intermediate Similarity	NPD5186	Approved
0.7541	Intermediate Similarity	NPD5183	Approved
0.7539	Intermediate Similarity	NPD5620	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD814	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD5294	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3984	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3983	Phase 3
0.7377	Intermediate Similarity	NPD4796	Discontinued
0.7363	Intermediate Similarity	NPD1742	Approved
0.7363	Intermediate Similarity	NPD1743	Approved
0.7363	Intermediate Similarity	NPD19	Approved
0.7316	Intermediate Similarity	NPD7149	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD6357	Discontinued
0.712	Intermediate Similarity	NPD7479	Phase 2
0.712	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7178	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD8027	Approved
0.7068	Intermediate Similarity	NPD3793	Phase 3
0.7068	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6238	Discontinued
0.7026	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7126	Discontinued
0.6995	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5071	Phase 2
0.6974	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.695	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6644	Discontinued
0.6923	Remote Similarity	NPD3641	Approved
0.6923	Remote Similarity	NPD3639	Approved
0.6923	Remote Similarity	NPD3640	Phase 3
0.6907	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD4166	Phase 2
0.6891	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4515	Suspended
0.6847	Remote Similarity	NPD5515	Phase 2
0.6845	Remote Similarity	NPD5967	Approved
0.6839	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3591	Approved
0.681	Remote Similarity	NPD3592	Approved
0.6806	Remote Similarity	NPD3437	Discontinued
0.6796	Remote Similarity	NPD6321	Discontinued
0.6792	Remote Similarity	NPD7225	Discontinued
0.6788	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7032	Approved
0.6782	Remote Similarity	NPD3631	Phase 3
0.6774	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4121	Phase 3
0.6757	Remote Similarity	NPD4120	Approved
0.672	Remote Similarity	NPD5741	Approved
0.672	Remote Similarity	NPD5742	Approved
0.672	Remote Similarity	NPD5743	Approved
0.6718	Remote Similarity	NPD5312	Approved
0.6718	Remote Similarity	NPD5313	Approved
0.6717	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD3416	Discontinued
0.6712	Remote Similarity	NPD7820	Phase 3
0.6712	Remote Similarity	NPD3912	Discontinued
0.6704	Remote Similarity	NPD7753	Approved
0.6704	Remote Similarity	NPD7752	Approved
0.6702	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4205	Phase 3
0.6683	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD4859	Phase 1
0.6682	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD4154	Approved
0.6667	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3124	Discontinued
0.6667	Remote Similarity	NPD6645	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD4885	Approved
0.665	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7248	Discontinued
0.6649	Remote Similarity	NPD1769	Discontinued
0.6633	Remote Similarity	NPD7281	Phase 3
0.6633	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7280	Phase 3
0.6629	Remote Similarity	NPD743	Approved
0.6623	Remote Similarity	NPD8359	Phase 2
0.662	Remote Similarity	NPD5562	Approved
0.662	Remote Similarity	NPD5561	Approved
0.6619	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD4539	Phase 1
0.6615	Remote Similarity	NPD5823	Approved
0.6612	Remote Similarity	NPD3141	Discontinued
0.6601	Remote Similarity	NPD2327	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD6790	Phase 1
0.659	Remote Similarity	NPD848	Approved
0.659	Remote Similarity	NPD850	Approved
0.659	Remote Similarity	NPD849	Approved
0.6584	Remote Similarity	NPD7326	Phase 3
0.6577	Remote Similarity	NPD7426	Phase 1
0.6575	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5937	Approved
0.6569	Remote Similarity	NPD5587	Approved
0.6564	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD3964	Approved
0.6553	Remote Similarity	NPD5582	Discontinued
0.6553	Remote Similarity	NPD5548	Clinical (unspecified phase)
0.655	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7877	Suspended
0.655	Remote Similarity	NPD8016	Phase 3
0.6544	Remote Similarity	NPD8149	Discontinued
0.6543	Remote Similarity	NPD5617	Suspended
0.6541	Remote Similarity	NPD4584	Approved
0.654	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6737	Phase 2
0.6526	Remote Similarity	NPD5658	Approved
0.6526	Remote Similarity	NPD6738	Phase 2
0.6524	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.652	Remote Similarity	NPD7668	Phase 2
0.651	Remote Similarity	NPD1309	Phase 2
0.651	Remote Similarity	NPD1307	Phase 2
0.6507	Remote Similarity	NPD6612	Phase 2
0.6505	Remote Similarity	NPD6493	Phase 3
0.6502	Remote Similarity	NPD7291	Discontinued
0.65	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD5293	Phase 2
0.6492	Remote Similarity	NPD5978	Approved
0.6492	Remote Similarity	NPD5977	Approved
0.6484	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1670	Discontinued
0.6468	Remote Similarity	NPD6744	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD3301	Approved
0.6459	Remote Similarity	NPD6757	Phase 3
0.6456	Remote Similarity	NPD6526	Approved
0.6449	Remote Similarity	NPD2916	Discontinued
0.6449	Remote Similarity	NPD6366	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD3515	Approved
0.6445	Remote Similarity	NPD3516	Approved
0.6436	Remote Similarity	NPD3564	Approved
0.6436	Remote Similarity	NPD3563	Approved
0.6436	Remote Similarity	NPD3562	Approved
0.6435	Remote Similarity	NPD7272	Discontinued
0.6429	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD7669	Phase 3
0.6425	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD8025	Phase 2
0.6421	Remote Similarity	NPD7110	Phase 1
0.6421	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD4981	Phase 2
0.6415	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD4354	Approved
0.641	Remote Similarity	NPD6379	Discontinued
0.641	Remote Similarity	NPD6107	Approved
0.6398	Remote Similarity	NPD7598	Phase 2
0.6396	Remote Similarity	NPD5997	Discontinued
0.6396	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD5512	Phase 3
0.6393	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.639	Remote Similarity	NPD5113	Approved
0.639	Remote Similarity	NPD5112	Approved
0.639	Remote Similarity	NPD5114	Approved
0.6389	Remote Similarity	NPD5860	Discontinued
0.6388	Remote Similarity	NPD3442	Approved
0.6388	Remote Similarity	NPD5139	Phase 1
0.6388	Remote Similarity	NPD3441	Approved
0.6381	Remote Similarity	NPD6874	Approved
0.6381	Remote Similarity	NPD3297	Approved
0.638	Remote Similarity	NPD5496	Approved
0.6378	Remote Similarity	NPD5847	Phase 1
0.6376	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD4642	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD3110	Approved
0.6369	Remote Similarity	NPD3109	Approved
0.6364	Remote Similarity	NPD6527	Approved
0.6364	Remote Similarity	NPD2335	Discontinued
0.6364	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5938	Phase 3
0.6359	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD4430	Phase 2
0.6359	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD5994	Discontinued
0.6359	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD6037	Discontinued

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