NPASS Compound

Structure

CID6974 OpenBabel06191715332D 30 34 0 0 1 0 0 0 0 0999 V2000 5.4168 3.8689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5508 -0.6311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6584 0.7294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4168 2.8689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1075 -1.7945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1913 -0.5954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0272 -2.3214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1948 0.0767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4522 -1.1311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1356 -0.3221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9527 -2.1311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9527 -0.1311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6847 -0.1311 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8187 -1.6311 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8187 -0.6311 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0307 -1.6493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1145 -0.4502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0867 -1.6311 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9667 -0.7833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7726 -0.9208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2946 0.1614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5508 1.3689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1356 -1.9401 0.0000 C 0 0 1 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 1.0867 -0.6311 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 3.2767 0.3498 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4168 0.8689 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6405 0.9178 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5508 2.3689 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6847 0.8689 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 16 2 0 0 0 0 8 17 2 0 0 0 0 9 10 1 0 0 0 0 10 25 1 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 25 1 0 0 0 0 13 2 1 6 0 0 0 13 30 1 0 0 0 0 14 11 1 6 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 13 1 6 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 23 1 1 0 0 0 18 25 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 20 23 1 0 0 0 0 20 24 1 0 0 0 0 21 26 2 0 0 0 0 21 28 1 0 0 0 0 22 27 2 0 0 0 0 22 29 1 0 0 0 0 22 30 1 0 0 0 0 23 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.2
Volume:	413.708
LogP:	2.456
LogD:	2.857
LogS:	-3.957
# Rotatable Bonds:	7
TPSA:	77.43
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.708
Synthetic Accessibility Score:	5.742
Fsp3:	0.609
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:	-4.784
MDCK Permeability:	4.304673711885698e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.054
30% Bioavailability (F30%):	0.334

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.953
Plasma Protein Binding (PPB):	55.0535888671875%
Volume Distribution (VD):	1.133
Pgp-substrate:	62.11293411254883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.082
CYP1A2-substrate:	0.259
CYP2C19-inhibitor:	0.158
CYP2C19-substrate:	0.956
CYP2C9-inhibitor:	0.105
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.809
CYP2D6-substrate:	0.778
CYP3A4-inhibitor:	0.91
CYP3A4-substrate:	0.89

ADMET: Excretion

Clearance (CL):	9.0
Half-life (T1/2):	0.298

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.46
Drug-inuced Liver Injury (DILI):	0.771
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.705
Maximum Recommended Daily Dose:	0.841
Skin Sensitization:	0.627
Carcinogencity:	0.271
Eye Corrosion:	0.006
Eye Irritation:	0.343
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC6974

Natural Product ID:	NPC6974
*Common Name:**	Alstolucine A
IUPAC Name:	n.a.
Synonyms:	Alstolucine A
Standard InCHIKey:	BPXHFWZHURFHEN-KBHVJUHDSA-N
Standard InCHI:	InChI=1S/C23H28N2O5/c1-4-29-22(27)30-13(2)15-12-25-10-9-23-16-7-5-6-8-17(16)24-20(23)19(21(26)28-3)14(15)11-18(23)25/h5-8,13-15,18,24H,4,9-12H2,1-3H3/t13-,14+,15-,18+,23-/m1/s1
SMILES:	CCOC(=O)O[C@H](C)[C@H]1CN2CC[C@@]34c5ccccc5NC4=C([C@H]1C[C@H]23)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651099
PubChem CID:	50899956
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002749] Strychnos alkaloids

*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
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17493	Alstonia spatulata	Species	Apocynaceae	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	3

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[511331]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.59	ug.mL-1	PMID[511331]

☑ 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 NPC6974 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	237
0.1-0.2	1003
0.2-0.3	3304
0.3-0.4	12705
0.4-0.5	19248
0.5-0.6	5134
0.6-0.7	876
0.7-0.8	154
0.8-0.85	15
0.85-0.9	11
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9627	High Similarity	NPC264482
0.9627	High Similarity	NPC203202
0.9509	High Similarity	NPC99043
0.9509	High Similarity	NPC218594
0.9212	High Similarity	NPC186669
0.9182	High Similarity	NPC193410
0.9125	High Similarity	NPC248117
0.9107	High Similarity	NPC159963
0.908	High Similarity	NPC167724
0.908	High Similarity	NPC223595
0.908	High Similarity	NPC224970
0.9006	High Similarity	NPC14994
0.9	High Similarity	NPC61013
0.896	High Similarity	NPC25401
0.8941	High Similarity	NPC97584
0.8765	High Similarity	NPC123241
0.875	High Similarity	NPC469726
0.875	High Similarity	NPC329338
0.872	High Similarity	NPC293458
0.8712	High Similarity	NPC36495
0.8274	Intermediate Similarity	NPC282339
0.8274	Intermediate Similarity	NPC99632
0.827	Intermediate Similarity	NPC1464
0.8138	Intermediate Similarity	NPC246140
0.8138	Intermediate Similarity	NPC195787
0.8085	Intermediate Similarity	NPC87714
0.8	Intermediate Similarity	NPC225319
0.7919	Intermediate Similarity	NPC214960
0.7919	Intermediate Similarity	NPC279527
0.7897	Intermediate Similarity	NPC189661
0.7895	Intermediate Similarity	NPC474058
0.7841	Intermediate Similarity	NPC214626
0.7841	Intermediate Similarity	NPC139085
0.7841	Intermediate Similarity	NPC210415
0.7841	Intermediate Similarity	NPC298851
0.7841	Intermediate Similarity	NPC21752
0.7841	Intermediate Similarity	NPC276993
0.7841	Intermediate Similarity	NPC251212
0.7841	Intermediate Similarity	NPC181138
0.7841	Intermediate Similarity	NPC293255
0.7826	Intermediate Similarity	NPC203628
0.7826	Intermediate Similarity	NPC22476
0.7791	Intermediate Similarity	NPC309531
0.7791	Intermediate Similarity	NPC472102
0.7778	Intermediate Similarity	NPC77777
0.7772	Intermediate Similarity	NPC5630
0.7766	Intermediate Similarity	NPC218733
0.7766	Intermediate Similarity	NPC138615
0.7766	Intermediate Similarity	NPC132874
0.7766	Intermediate Similarity	NPC265642
0.7709	Intermediate Similarity	NPC260075
0.7674	Intermediate Similarity	NPC113946
0.7663	Intermediate Similarity	NPC181928
0.766	Intermediate Similarity	NPC303214
0.765	Intermediate Similarity	NPC52262
0.7644	Intermediate Similarity	NPC472120
0.7644	Intermediate Similarity	NPC472101
0.7644	Intermediate Similarity	NPC232600
0.7638	Intermediate Similarity	NPC195636
0.7588	Intermediate Similarity	NPC243756
0.7581	Intermediate Similarity	NPC473298
0.7581	Intermediate Similarity	NPC105055
0.7581	Intermediate Similarity	NPC22689
0.7558	Intermediate Similarity	NPC161827
0.7543	Intermediate Similarity	NPC472117
0.7525	Intermediate Similarity	NPC476069
0.7513	Intermediate Similarity	NPC34717
0.75	Intermediate Similarity	NPC478076
0.7488	Intermediate Similarity	NPC128476
0.7488	Intermediate Similarity	NPC223242
0.7458	Intermediate Similarity	NPC472106
0.7456	Intermediate Similarity	NPC264589
0.7444	Intermediate Similarity	NPC285622
0.7444	Intermediate Similarity	NPC96901
0.7436	Intermediate Similarity	NPC475147
0.7435	Intermediate Similarity	NPC90967
0.743	Intermediate Similarity	NPC472118
0.7429	Intermediate Similarity	NPC63210
0.7429	Intermediate Similarity	NPC243673
0.7429	Intermediate Similarity	NPC148468
0.7429	Intermediate Similarity	NPC310403
0.7429	Intermediate Similarity	NPC263709
0.7429	Intermediate Similarity	NPC97380
0.7427	Intermediate Similarity	NPC473329
0.7416	Intermediate Similarity	NPC139373
0.7396	Intermediate Similarity	NPC100863
0.7384	Intermediate Similarity	NPC475763
0.7379	Intermediate Similarity	NPC19175
0.7371	Intermediate Similarity	NPC471512
0.736	Intermediate Similarity	NPC470069
0.736	Intermediate Similarity	NPC52059
0.7348	Intermediate Similarity	NPC476425
0.7345	Intermediate Similarity	NPC286871
0.7341	Intermediate Similarity	NPC122106
0.732	Intermediate Similarity	NPC312870
0.732	Intermediate Similarity	NPC254240
0.732	Intermediate Similarity	NPC199851
0.732	Intermediate Similarity	NPC294909
0.732	Intermediate Similarity	NPC128265
0.7314	Intermediate Similarity	NPC469536
0.7286	Intermediate Similarity	NPC475133
0.7282	Intermediate Similarity	NPC469732
0.7277	Intermediate Similarity	NPC131977
0.7273	Intermediate Similarity	NPC153694
0.7273	Intermediate Similarity	NPC211525
0.725	Intermediate Similarity	NPC269449
0.7249	Intermediate Similarity	NPC316405
0.7247	Intermediate Similarity	NPC472121
0.7247	Intermediate Similarity	NPC176983
0.7243	Intermediate Similarity	NPC301501
0.7235	Intermediate Similarity	NPC190945
0.7209	Intermediate Similarity	NPC469450
0.7202	Intermediate Similarity	NPC130251
0.7191	Intermediate Similarity	NPC201424
0.7184	Intermediate Similarity	NPC154602
0.7181	Intermediate Similarity	NPC472209
0.7178	Intermediate Similarity	NPC119722
0.7174	Intermediate Similarity	NPC476441
0.7165	Intermediate Similarity	NPC162440
0.7163	Intermediate Similarity	NPC151171
0.715	Intermediate Similarity	NPC221687
0.7143	Intermediate Similarity	NPC469452
0.7143	Intermediate Similarity	NPC469451
0.7135	Intermediate Similarity	NPC476326
0.7127	Intermediate Similarity	NPC472115
0.7127	Intermediate Similarity	NPC472114
0.7126	Intermediate Similarity	NPC318086
0.7119	Intermediate Similarity	NPC29285
0.7113	Intermediate Similarity	NPC245916
0.7088	Intermediate Similarity	NPC470971
0.7085	Intermediate Similarity	NPC329833
0.7078	Intermediate Similarity	NPC329932
0.707	Intermediate Similarity	NPC291173
0.7064	Intermediate Similarity	NPC469722
0.7062	Intermediate Similarity	NPC19692
0.7062	Intermediate Similarity	NPC220151
0.7056	Intermediate Similarity	NPC67904
0.7056	Intermediate Similarity	NPC138830
0.7022	Intermediate Similarity	NPC36836
0.7022	Intermediate Similarity	NPC63370
0.7021	Intermediate Similarity	NPC476428
0.7021	Intermediate Similarity	NPC475962
0.7016	Intermediate Similarity	NPC21425
0.6979	Remote Similarity	NPC63199
0.6979	Remote Similarity	NPC102338
0.6979	Remote Similarity	NPC196251
0.6979	Remote Similarity	NPC111602
0.6973	Remote Similarity	NPC177261
0.697	Remote Similarity	NPC475489
0.6967	Remote Similarity	NPC115588
0.6967	Remote Similarity	NPC231924
0.6966	Remote Similarity	NPC473297
0.6961	Remote Similarity	NPC469741
0.6959	Remote Similarity	NPC301760
0.6957	Remote Similarity	NPC469915
0.6957	Remote Similarity	NPC126556
0.6949	Remote Similarity	NPC285381
0.6939	Remote Similarity	NPC97100
0.6939	Remote Similarity	NPC473375
0.6915	Remote Similarity	NPC321211
0.6912	Remote Similarity	NPC154922
0.6911	Remote Similarity	NPC322621
0.6911	Remote Similarity	NPC49184
0.6908	Remote Similarity	NPC234772
0.6907	Remote Similarity	NPC472097
0.6901	Remote Similarity	NPC473458
0.6893	Remote Similarity	NPC314223
0.689	Remote Similarity	NPC52254
0.6888	Remote Similarity	NPC243626
0.6881	Remote Similarity	NPC477161
0.6879	Remote Similarity	NPC469537
0.6866	Remote Similarity	NPC475448
0.6866	Remote Similarity	NPC246983
0.6851	Remote Similarity	NPC471122
0.6842	Remote Similarity	NPC82070
0.6839	Remote Similarity	NPC472103
0.6831	Remote Similarity	NPC313757
0.6825	Remote Similarity	NPC475094
0.6824	Remote Similarity	NPC471123
0.6823	Remote Similarity	NPC469460
0.6816	Remote Similarity	NPC162730
0.6816	Remote Similarity	NPC475223
0.6813	Remote Similarity	NPC315368
0.6812	Remote Similarity	NPC221100
0.6812	Remote Similarity	NPC234078
0.6806	Remote Similarity	NPC477159
0.6802	Remote Similarity	NPC230313
0.6789	Remote Similarity	NPC11149
0.6786	Remote Similarity	NPC55493
0.6776	Remote Similarity	NPC472762
0.6769	Remote Similarity	NPC474059
0.6769	Remote Similarity	NPC329858
0.6763	Remote Similarity	NPC186284
0.6763	Remote Similarity	NPC22082
0.6761	Remote Similarity	NPC472100
0.6757	Remote Similarity	NPC113455
0.6755	Remote Similarity	NPC13367
0.6755	Remote Similarity	NPC475097
0.6749	Remote Similarity	NPC268077
0.6744	Remote Similarity	NPC471513

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 NPC6974 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	459
0.2-0.3	723
0.3-0.4	1263
0.4-0.5	3831
0.5-0.6	2391
0.6-0.7	315
0.7-0.8	20
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
0.732	Intermediate Similarity	NPD4501	Approved
0.732	Intermediate Similarity	NPD4500	Approved
0.7251	Intermediate Similarity	NPD4041	Approved
0.7235	Intermediate Similarity	NPD2435	Approved
0.7232	Intermediate Similarity	NPD7114	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7036	Phase 3
0.7167	Intermediate Similarity	NPD7035	Approved
0.7143	Intermediate Similarity	NPD3399	Approved
0.7127	Intermediate Similarity	NPD8002	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD8003	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7244	Discontinued
0.7029	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6570	Approved
0.7022	Intermediate Similarity	NPD6571	Approved
0.7011	Intermediate Similarity	NPD1802	Approved
0.7011	Intermediate Similarity	NPD1801	Approved
0.6984	Remote Similarity	NPD8281	Discontinued
0.6971	Remote Similarity	NPD7528	Approved
0.6949	Remote Similarity	NPD2948	Discontinued
0.6941	Remote Similarity	NPD3170	Approved
0.6905	Remote Similarity	NPD5185	Approved
0.6905	Remote Similarity	NPD5184	Approved
0.6905	Remote Similarity	NPD5182	Approved
0.6882	Remote Similarity	NPD2670	Approved
0.6862	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4607	Approved
0.6845	Remote Similarity	NPD7940	Phase 3
0.6839	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2923	Approved
0.6818	Remote Similarity	NPD3352	Approved
0.6811	Remote Similarity	NPD2037	Approved
0.68	Remote Similarity	NPD6185	Discontinued
0.6791	Remote Similarity	NPD5997	Discontinued
0.6789	Remote Similarity	NPD4329	Approved
0.6789	Remote Similarity	NPD4330	Approved
0.6774	Remote Similarity	NPD5183	Approved
0.6774	Remote Similarity	NPD5186	Approved
0.6774	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD3422	Phase 3
0.6755	Remote Similarity	NPD3423	Phase 2
0.6754	Remote Similarity	NPD3470	Approved
0.6754	Remote Similarity	NPD3471	Approved
0.6743	Remote Similarity	NPD7487	Discontinued
0.6742	Remote Similarity	NPD4513	Discontinued
0.6739	Remote Similarity	NPD8008	Approved
0.6739	Remote Similarity	NPD8007	Approved
0.6738	Remote Similarity	NPD2431	Approved
0.6738	Remote Similarity	NPD2432	Approved
0.6737	Remote Similarity	NPD7775	Approved
0.6737	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD3828	Approved
0.6723	Remote Similarity	NPD6758	Approved
0.6722	Remote Similarity	NPD4120	Approved
0.6722	Remote Similarity	NPD4121	Phase 3
0.672	Remote Similarity	NPD2455	Approved
0.672	Remote Similarity	NPD2454	Approved
0.6704	Remote Similarity	NPD7606	Phase 3
0.6685	Remote Similarity	NPD5743	Approved
0.6685	Remote Similarity	NPD5742	Approved
0.6685	Remote Similarity	NPD5741	Approved
0.6684	Remote Similarity	NPD3436	Approved
0.6684	Remote Similarity	NPD4499	Approved
0.6684	Remote Similarity	NPD3792	Approved
0.6667	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3625	Discontinued
0.6667	Remote Similarity	NPD5466	Approved
0.6651	Remote Similarity	NPD6770	Approved
0.665	Remote Similarity	NPD5504	Discontinued
0.6649	Remote Similarity	NPD7881	Approved
0.6647	Remote Similarity	NPD1109	Approved
0.6647	Remote Similarity	NPD1110	Approved
0.6634	Remote Similarity	NPD6805	Discontinued
0.663	Remote Similarity	NPD2506	Approved
0.6629	Remote Similarity	NPD7478	Approved
0.6618	Remote Similarity	NPD4506	Discontinued
0.6613	Remote Similarity	NPD5430	Discontinued
0.6613	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD8630	Approved
0.659	Remote Similarity	NPD2567	Approved
0.659	Remote Similarity	NPD2569	Approved
0.658	Remote Similarity	NPD3435	Discontinued
0.657	Remote Similarity	NPD2509	Approved
0.657	Remote Similarity	NPD2510	Approved
0.657	Remote Similarity	NPD4859	Phase 1
0.6562	Remote Similarity	NPD3782	Discontinued
0.6552	Remote Similarity	NPD4600	Approved
0.6552	Remote Similarity	NPD4601	Approved
0.6546	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD2404	Discontinued
0.6541	Remote Similarity	NPD7600	Phase 2
0.6537	Remote Similarity	NPD7205	Discontinued
0.6534	Remote Similarity	NPD6768	Approved
0.652	Remote Similarity	NPD6238	Discontinued
0.6519	Remote Similarity	NPD7670	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2994	Approved
0.65	Remote Similarity	NPD5941	Approved
0.65	Remote Similarity	NPD4888	Discontinued
0.65	Remote Similarity	NPD5942	Approved
0.6497	Remote Similarity	NPD2820	Phase 3
0.6486	Remote Similarity	NPD2427	Approved
0.6474	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1663	Discontinued
0.6458	Remote Similarity	NPD3948	Discontinued
0.6458	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD1626	Approved
0.6455	Remote Similarity	NPD3468	Approved
0.6453	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD2790	Discontinued
0.6446	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD2115	Approved
0.6442	Remote Similarity	NPD2117	Pre-registration
0.6442	Remote Similarity	NPD2116	Approved
0.6441	Remote Similarity	NPD2365	Approved
0.644	Remote Similarity	NPD7854	Phase 2
0.644	Remote Similarity	NPD3377	Discontinued
0.6432	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD6622	Phase 1
0.6425	Remote Similarity	NPD7295	Approved
0.6425	Remote Similarity	NPD3947	Discontinued
0.6425	Remote Similarity	NPD6017	Discontinued
0.6422	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD6891	Phase 2
0.6411	Remote Similarity	NPD4082	Approved
0.64	Remote Similarity	NPD4370	Phase 3
0.64	Remote Similarity	NPD3884	Discontinued
0.6398	Remote Similarity	NPD7599	Phase 2
0.6398	Remote Similarity	NPD4493	Discontinued
0.6386	Remote Similarity	NPD2946	Phase 2
0.6383	Remote Similarity	NPD3790	Phase 2
0.6382	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7962	Phase 2
0.6372	Remote Similarity	NPD7878	Phase 2
0.6369	Remote Similarity	NPD5918	Discontinued
0.6368	Remote Similarity	NPD4492	Approved
0.6368	Remote Similarity	NPD4494	Approved
0.6368	Remote Similarity	NPD6625	Approved
0.6364	Remote Similarity	NPD4311	Approved
0.6364	Remote Similarity	NPD3032	Approved
0.6364	Remote Similarity	NPD3031	Approved
0.6364	Remote Similarity	NPD3030	Approved
0.6359	Remote Similarity	NPD6878	Phase 2
0.6359	Remote Similarity	NPD6879	Phase 2
0.635	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.634	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.634	Remote Similarity	NPD5600	Discontinued
0.634	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD7795	Phase 2
0.6333	Remote Similarity	NPD5933	Phase 3
0.6333	Remote Similarity	NPD5932	Phase 3
0.6333	Remote Similarity	NPD5931	Phase 3
0.6329	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6326	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD6659	Phase 2
0.6313	Remote Similarity	NPD5024	Approved
0.6313	Remote Similarity	NPD7082	Approved
0.6313	Remote Similarity	NPD6557	Phase 2
0.6313	Remote Similarity	NPD1625	Approved
0.631	Remote Similarity	NPD6637	Approved
0.631	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD6342	Discontinued
0.6298	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD6176	Phase 1
0.6294	Remote Similarity	NPD9567	Approved
0.6294	Remote Similarity	NPD553	Approved
0.6294	Remote Similarity	NPD552	Approved
0.6293	Remote Similarity	NPD4668	Phase 2
0.629	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7105	Phase 1
0.629	Remote Similarity	NPD2836	Approved
0.6286	Remote Similarity	NPD4596	Phase 1
0.6278	Remote Similarity	NPD7259	Approved
0.6278	Remote Similarity	NPD7688	Phase 1
0.6278	Remote Similarity	NPD2387	Approved
0.6275	Remote Similarity	NPD5411	Discontinued
0.627	Remote Similarity	NPD5086	Approved
0.6269	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5928	Phase 1
0.6268	Remote Similarity	NPD8283	Approved
0.6268	Remote Similarity	NPD56	Approved
0.6268	Remote Similarity	NPD8282	Approved
0.6264	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD4412	Phase 2
0.6262	Remote Similarity	NPD6874	Approved
0.6257	Remote Similarity	NPD6566	Discontinued
0.6256	Remote Similarity	NPD8423	Phase 2
0.6256	Remote Similarity	NPD8399	Phase 1
0.625	Remote Similarity	NPD6532	Discontinued
0.6244	Remote Similarity	NPD7470	Discontinued
0.6243	Remote Similarity	NPD6489	Phase 3
0.6243	Remote Similarity	NPD1069	Approved
0.6243	Remote Similarity	NPD1070	Approved
0.6238	Remote Similarity	NPD5042	Phase 1
0.6231	Remote Similarity	NPD8167	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