NPASS Compound

Structure

CID329338 OpenBabel06191716212D 26 30 0 0 1 0 0 0 0 0999 V2000 -4.5508 -0.6311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9684 1.8625 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 0 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 1 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 -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 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 -3.2767 0.3498 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4934 0.2824 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 1 11 1 0 0 0 0 2 26 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 2 0 0 0 0 6 15 2 0 0 0 0 7 8 1 0 0 0 0 8 22 1 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 22 1 0 0 0 0 11 23 2 0 0 0 0 12 9 1 1 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 11 1 6 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 20 1 6 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 20 7 1 1 0 0 0 22 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.16
Volume:	353.03
LogP:	0.534
LogD:	0.055
LogS:	-1.561
# Rotatable Bonds:	3
TPSA:	78.79
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.463
Synthetic Accessibility Score:	6.088
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.425
MDCK Permeability:	4.393839481053874e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.947
Human Intestinal Absorption (HIA):	0.98
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.287
Plasma Protein Binding (PPB):	29.750293731689453%
Volume Distribution (VD):	1.37
Pgp-substrate:	69.23191833496094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.374
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.917
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.243
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.636
CYP3A4-inhibitor:	0.113
CYP3A4-substrate:	0.875

ADMET: Excretion

Clearance (CL):	9.439
Half-life (T1/2):	0.931

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.688
Drug-inuced Liver Injury (DILI):	0.072
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.856
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.442
Carcinogencity:	0.871
Eye Corrosion:	0.033
Eye Irritation:	0.216
Respiratory Toxicity:	0.916

Download Data

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

Natural Product: NPC329338

Natural Product ID:	NPC329338
*Common Name:**	Alstolucine C
IUPAC Name:	n.a.
Synonyms:	Alstolucine C
Standard InCHIKey:	DHECBQUIZKPOOU-SRQGGJSVSA-N
Standard InCHI:	InChI=1S/C20H22N2O4/c1-11(23)13-10-22(25)8-7-20-14-5-3-4-6-15(14)21-18(20)17(19(24)26-2)12(13)9-16(20)22/h3-6,12-13,16,21H,7-10H2,1-2H3/t12-,13-,16-,20+,22?/m0/s1
SMILES:	COC(=O)C1=C2Nc3c([C@@]42[C@@H]2C[C@H]1[C@@H](CN2(=O)CC4)C(=O)C)cccc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651101
PubChem CID:	50900048
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[573749]

☑ 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 NPC329338 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	251
0.1-0.2	1088
0.2-0.3	4746
0.3-0.4	17520
0.4-0.5	14061
0.5-0.6	4179
0.6-0.7	676
0.7-0.8	144
0.8-0.85	13
0.85-0.9	10
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469726
0.9494	High Similarity	NPC167724
0.9494	High Similarity	NPC223595
0.9494	High Similarity	NPC224970
0.9114	High Similarity	NPC193410
0.9057	High Similarity	NPC248117
0.8931	High Similarity	NPC61013
0.8882	High Similarity	NPC293458
0.875	High Similarity	NPC6974
0.8743	High Similarity	NPC264482
0.8743	High Similarity	NPC203202
0.8696	High Similarity	NPC123241
0.8642	High Similarity	NPC36495
0.8639	High Similarity	NPC99043
0.8639	High Similarity	NPC218594
0.84	Intermediate Similarity	NPC14994
0.8363	Intermediate Similarity	NPC186669
0.8333	Intermediate Similarity	NPC97584
0.8276	Intermediate Similarity	NPC159963
0.8251	Intermediate Similarity	NPC469732
0.8204	Intermediate Similarity	NPC282339
0.8204	Intermediate Similarity	NPC99632
0.8156	Intermediate Similarity	NPC25401
0.8087	Intermediate Similarity	NPC138615
0.8087	Intermediate Similarity	NPC265642
0.8087	Intermediate Similarity	NPC132874
0.8087	Intermediate Similarity	NPC218733
0.7964	Intermediate Similarity	NPC469536
0.7929	Intermediate Similarity	NPC225319
0.7849	Intermediate Similarity	NPC279527
0.7849	Intermediate Similarity	NPC214960
0.7841	Intermediate Similarity	NPC260075
0.7705	Intermediate Similarity	NPC5630
0.7665	Intermediate Similarity	NPC318086
0.7663	Intermediate Similarity	NPC22476
0.7663	Intermediate Similarity	NPC203628
0.7622	Intermediate Similarity	NPC469537
0.7619	Intermediate Similarity	NPC475763
0.7602	Intermediate Similarity	NPC113946
0.7539	Intermediate Similarity	NPC1464
0.7515	Intermediate Similarity	NPC243756
0.7514	Intermediate Similarity	NPC474058
0.75	Intermediate Similarity	NPC303214
0.7472	Intermediate Similarity	NPC251212
0.7472	Intermediate Similarity	NPC214626
0.7472	Intermediate Similarity	NPC139085
0.747	Intermediate Similarity	NPC190945
0.7444	Intermediate Similarity	NPC476326
0.7427	Intermediate Similarity	NPC478076
0.7423	Intermediate Similarity	NPC195787
0.7423	Intermediate Similarity	NPC246140
0.7396	Intermediate Similarity	NPC232600
0.7391	Intermediate Similarity	NPC52262
0.7371	Intermediate Similarity	NPC87714
0.736	Intermediate Similarity	NPC472118
0.7353	Intermediate Similarity	NPC473329
0.733	Intermediate Similarity	NPC100863
0.7322	Intermediate Similarity	NPC476428
0.7314	Intermediate Similarity	NPC472102
0.7314	Intermediate Similarity	NPC309531
0.7312	Intermediate Similarity	NPC181928
0.7288	Intermediate Similarity	NPC52059
0.7288	Intermediate Similarity	NPC470069
0.7283	Intermediate Similarity	NPC161827
0.7282	Intermediate Similarity	NPC475147
0.7267	Intermediate Similarity	NPC122106
0.7234	Intermediate Similarity	NPC473298
0.7229	Intermediate Similarity	NPC130251
0.7214	Intermediate Similarity	NPC189661
0.7182	Intermediate Similarity	NPC96901
0.7182	Intermediate Similarity	NPC285622
0.7176	Intermediate Similarity	NPC264589
0.7175	Intermediate Similarity	NPC286871
0.7173	Intermediate Similarity	NPC34717
0.7159	Intermediate Similarity	NPC263709
0.7159	Intermediate Similarity	NPC97380
0.7159	Intermediate Similarity	NPC63210
0.7159	Intermediate Similarity	NPC148468
0.7159	Intermediate Similarity	NPC310403
0.7159	Intermediate Similarity	NPC243673
0.7143	Intermediate Similarity	NPC36836
0.7143	Intermediate Similarity	NPC63370
0.7136	Intermediate Similarity	NPC475133
0.7112	Intermediate Similarity	NPC472209
0.711	Intermediate Similarity	NPC154602
0.7108	Intermediate Similarity	NPC77777
0.71	Intermediate Similarity	NPC269449
0.7098	Intermediate Similarity	NPC90967
0.7088	Intermediate Similarity	NPC298851
0.7088	Intermediate Similarity	NPC476425
0.7088	Intermediate Similarity	NPC276993
0.7088	Intermediate Similarity	NPC293255
0.7088	Intermediate Similarity	NPC21752
0.7088	Intermediate Similarity	NPC210415
0.7088	Intermediate Similarity	NPC181138
0.7079	Intermediate Similarity	NPC176983
0.7079	Intermediate Similarity	NPC472120
0.7079	Intermediate Similarity	NPC472117
0.7079	Intermediate Similarity	NPC472101
0.7079	Intermediate Similarity	NPC469741
0.7079	Intermediate Similarity	NPC472121
0.703	Intermediate Similarity	NPC119722
0.7022	Intermediate Similarity	NPC201424
0.702	Intermediate Similarity	NPC185742
0.702	Intermediate Similarity	NPC475847
0.7006	Intermediate Similarity	NPC211525
0.7006	Intermediate Similarity	NPC153694
0.7	Intermediate Similarity	NPC472106
0.6995	Remote Similarity	NPC220151
0.6995	Remote Similarity	NPC19692
0.6986	Remote Similarity	NPC115588
0.6982	Remote Similarity	NPC301760
0.6976	Remote Similarity	NPC195636
0.6963	Remote Similarity	NPC105055
0.6963	Remote Similarity	NPC22689
0.6961	Remote Similarity	NPC472114
0.6961	Remote Similarity	NPC472115
0.6949	Remote Similarity	NPC29285
0.6947	Remote Similarity	NPC21425
0.6923	Remote Similarity	NPC162440
0.6919	Remote Similarity	NPC476441
0.6907	Remote Similarity	NPC221687
0.6907	Remote Similarity	NPC474121
0.6893	Remote Similarity	NPC473297
0.6875	Remote Similarity	NPC285381
0.6875	Remote Similarity	NPC476069
0.6872	Remote Similarity	NPC245916
0.6856	Remote Similarity	NPC472295
0.6856	Remote Similarity	NPC81802
0.6856	Remote Similarity	NPC472210
0.6856	Remote Similarity	NPC269886
0.6856	Remote Similarity	NPC247735
0.6854	Remote Similarity	NPC223242
0.685	Remote Similarity	NPC329833
0.6848	Remote Similarity	NPC292265
0.6845	Remote Similarity	NPC321211
0.6842	Remote Similarity	NPC322621
0.6842	Remote Similarity	NPC128476
0.6833	Remote Similarity	NPC315368
0.6823	Remote Similarity	NPC63199
0.6823	Remote Similarity	NPC102338
0.6823	Remote Similarity	NPC196251
0.6823	Remote Similarity	NPC111602
0.6812	Remote Similarity	NPC126556
0.6811	Remote Similarity	NPC177261
0.6791	Remote Similarity	NPC139373
0.6784	Remote Similarity	NPC471512
0.6758	Remote Similarity	NPC313757
0.6754	Remote Similarity	NPC469460
0.675	Remote Similarity	NPC137589
0.6746	Remote Similarity	NPC471123
0.6745	Remote Similarity	NPC19175
0.6737	Remote Similarity	NPC470317
0.6735	Remote Similarity	NPC243626
0.6734	Remote Similarity	NPC67904
0.6734	Remote Similarity	NPC138830
0.6712	Remote Similarity	NPC151171
0.6701	Remote Similarity	NPC329858
0.6701	Remote Similarity	NPC97100
0.6701	Remote Similarity	NPC473375
0.6685	Remote Similarity	NPC471122
0.6667	Remote Similarity	NPC162730
0.6667	Remote Similarity	NPC318183
0.6667	Remote Similarity	NPC131977
0.665	Remote Similarity	NPC312870
0.665	Remote Similarity	NPC230313
0.665	Remote Similarity	NPC477161
0.665	Remote Similarity	NPC199851
0.665	Remote Similarity	NPC128265
0.665	Remote Similarity	NPC254240
0.665	Remote Similarity	NPC294909
0.6649	Remote Similarity	NPC477159
0.6636	Remote Similarity	NPC301501
0.6633	Remote Similarity	NPC55493
0.663	Remote Similarity	NPC222029
0.6629	Remote Similarity	NPC314223
0.6628	Remote Similarity	NPC315051
0.6622	Remote Similarity	NPC469451
0.6616	Remote Similarity	NPC472293
0.6615	Remote Similarity	NPC313293
0.6615	Remote Similarity	NPC314333
0.6606	Remote Similarity	NPC469450
0.6596	Remote Similarity	NPC13367
0.6595	Remote Similarity	NPC278887
0.659	Remote Similarity	NPC186284
0.659	Remote Similarity	NPC22082
0.6588	Remote Similarity	NPC173295
0.6585	Remote Similarity	NPC285192
0.6584	Remote Similarity	NPC474116
0.657	Remote Similarity	NPC469560
0.6564	Remote Similarity	NPC284706
0.6564	Remote Similarity	NPC316405
0.6562	Remote Similarity	NPC329932
0.6548	Remote Similarity	NPC472292
0.6547	Remote Similarity	NPC469452
0.6547	Remote Similarity	NPC469722
0.6545	Remote Similarity	NPC11149
0.6541	Remote Similarity	NPC471124
0.6537	Remote Similarity	NPC478075
0.6536	Remote Similarity	NPC66936

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 NPC329338 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	490
0.2-0.3	783
0.3-0.4	1263
0.4-0.5	3698
0.5-0.6	2419
0.6-0.7	318
0.7-0.8	30
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
0.747	Intermediate Similarity	NPD2435	Approved
0.7381	Intermediate Similarity	NPD4041	Approved
0.7368	Intermediate Similarity	NPD3399	Approved
0.7257	Intermediate Similarity	NPD7114	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7036	Phase 3
0.7191	Intermediate Similarity	NPD7035	Approved
0.7168	Intermediate Similarity	NPD2948	Discontinued
0.7151	Intermediate Similarity	NPD8003	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8002	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6570	Approved
0.7143	Intermediate Similarity	NPD6571	Approved
0.7119	Intermediate Similarity	NPD7244	Discontinued
0.7097	Intermediate Similarity	NPD8281	Discontinued
0.7052	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7940	Phase 3
0.6944	Remote Similarity	NPD8008	Approved
0.6944	Remote Similarity	NPD8007	Approved
0.6941	Remote Similarity	NPD2923	Approved
0.6923	Remote Similarity	NPD2037	Approved
0.6919	Remote Similarity	NPD6185	Discontinued
0.6898	Remote Similarity	NPD4330	Approved
0.6898	Remote Similarity	NPD4329	Approved
0.6885	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4607	Approved
0.6862	Remote Similarity	NPD3471	Approved
0.6862	Remote Similarity	NPD3470	Approved
0.6848	Remote Similarity	NPD2431	Approved
0.6848	Remote Similarity	NPD2432	Approved
0.6845	Remote Similarity	NPD7881	Approved
0.6839	Remote Similarity	NPD3352	Approved
0.6839	Remote Similarity	NPD1802	Approved
0.6839	Remote Similarity	NPD1801	Approved
0.6839	Remote Similarity	NPD6758	Approved
0.6831	Remote Similarity	NPD2455	Approved
0.6831	Remote Similarity	NPD2454	Approved
0.68	Remote Similarity	NPD7528	Approved
0.6791	Remote Similarity	NPD3792	Approved
0.6763	Remote Similarity	NPD7487	Discontinued
0.6761	Remote Similarity	NPD4513	Discontinued
0.6755	Remote Similarity	NPD7775	Approved
0.6753	Remote Similarity	NPD5504	Discontinued
0.6743	Remote Similarity	NPD7478	Approved
0.674	Remote Similarity	NPD2506	Approved
0.6738	Remote Similarity	NPD3948	Discontinued
0.6726	Remote Similarity	NPD5185	Approved
0.6726	Remote Similarity	NPD5182	Approved
0.6726	Remote Similarity	NPD5184	Approved
0.6723	Remote Similarity	NPD7670	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7606	Phase 3
0.672	Remote Similarity	NPD3377	Discontinued
0.6706	Remote Similarity	NPD2670	Approved
0.6702	Remote Similarity	NPD3436	Approved
0.6684	Remote Similarity	NPD3435	Discontinued
0.6684	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6770	Approved
0.6667	Remote Similarity	NPD3170	Approved
0.6667	Remote Similarity	NPD3782	Discontinued
0.6667	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4500	Approved
0.665	Remote Similarity	NPD4501	Approved
0.6649	Remote Similarity	NPD2404	Discontinued
0.6634	Remote Similarity	NPD4506	Discontinued
0.6615	Remote Similarity	NPD4499	Approved
0.6613	Remote Similarity	NPD5186	Approved
0.6613	Remote Similarity	NPD5183	Approved
0.6596	Remote Similarity	NPD3422	Phase 3
0.6596	Remote Similarity	NPD5466	Approved
0.6596	Remote Similarity	NPD3423	Phase 2
0.6593	Remote Similarity	NPD2427	Approved
0.659	Remote Similarity	NPD3625	Discontinued
0.6583	Remote Similarity	NPD3828	Approved
0.6561	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD3468	Approved
0.6556	Remote Similarity	NPD2790	Discontinued
0.6534	Remote Similarity	NPD6017	Discontinued
0.6513	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4082	Approved
0.6497	Remote Similarity	NPD3884	Discontinued
0.6491	Remote Similarity	NPD1071	Clinical (unspecified phase)
0.649	Remote Similarity	NPD4493	Discontinued
0.6485	Remote Similarity	NPD6805	Discontinued
0.6474	Remote Similarity	NPD1109	Approved
0.6474	Remote Similarity	NPD1110	Approved
0.6467	Remote Similarity	NPD4311	Approved
0.6459	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD4494	Approved
0.6459	Remote Similarity	NPD4492	Approved
0.6457	Remote Similarity	NPD6768	Approved
0.6455	Remote Similarity	NPD5997	Discontinued
0.6452	Remote Similarity	NPD5430	Discontinued
0.6452	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD8630	Approved
0.6441	Remote Similarity	NPD7295	Approved
0.6439	Remote Similarity	NPD3947	Discontinued
0.6425	Remote Similarity	NPD4888	Discontinued
0.6422	Remote Similarity	NPD6532	Discontinued
0.642	Remote Similarity	NPD2820	Phase 3
0.642	Remote Similarity	NPD2994	Approved
0.642	Remote Similarity	NPD7082	Approved
0.6402	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.639	Remote Similarity	NPD7205	Discontinued
0.6386	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD5918	Discontinued
0.6384	Remote Similarity	NPD7259	Approved
0.6379	Remote Similarity	NPD1626	Approved
0.6377	Remote Similarity	NPD4596	Phase 1
0.6368	Remote Similarity	NPD7854	Phase 2
0.6364	Remote Similarity	NPD2365	Approved
0.6364	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD4412	Phase 2
0.6358	Remote Similarity	NPD2115	Approved
0.6358	Remote Similarity	NPD2117	Pre-registration
0.6358	Remote Similarity	NPD2116	Approved
0.6348	Remote Similarity	NPD5933	Phase 3
0.6348	Remote Similarity	NPD5931	Phase 3
0.6348	Remote Similarity	NPD5932	Phase 3
0.6346	Remote Similarity	NPD4859	Phase 1
0.6346	Remote Similarity	NPD2509	Approved
0.6346	Remote Similarity	NPD2510	Approved
0.6338	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5195	Discontinued
0.6333	Remote Similarity	NPD5941	Approved
0.6333	Remote Similarity	NPD5942	Approved
0.6324	Remote Similarity	NPD4601	Approved
0.6324	Remote Similarity	NPD4600	Approved
0.6322	Remote Similarity	NPD2567	Approved
0.6322	Remote Similarity	NPD2569	Approved
0.6322	Remote Similarity	NPD6342	Discontinued
0.6319	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3790	Phase 2
0.6303	Remote Similarity	NPD2946	Phase 2
0.6298	Remote Similarity	NPD1405	Approved
0.6294	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6238	Discontinued
0.6286	Remote Similarity	NPD3893	Discontinued
0.628	Remote Similarity	NPD56	Approved
0.628	Remote Similarity	NPD8283	Approved
0.628	Remote Similarity	NPD8282	Approved
0.628	Remote Similarity	NPD3030	Approved
0.628	Remote Similarity	NPD3031	Approved
0.628	Remote Similarity	NPD3032	Approved
0.6279	Remote Similarity	NPD1527	Phase 2
0.6274	Remote Similarity	NPD4455	Discontinued
0.6271	Remote Similarity	NPD6566	Discontinued
0.627	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5600	Discontinued
0.6268	Remote Similarity	NPD4022	Approved
0.6268	Remote Similarity	NPD3472	Approved
0.6264	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7795	Phase 2
0.6257	Remote Similarity	NPD6622	Phase 1
0.625	Remote Similarity	NPD4370	Phase 3
0.625	Remote Similarity	NPD3304	Phase 2
0.6244	Remote Similarity	NPD2397	Discontinued
0.6243	Remote Similarity	NPD4682	Phase 2
0.6238	Remote Similarity	NPD6529	Discontinued
0.6237	Remote Similarity	NPD7599	Phase 2
0.6236	Remote Similarity	NPD5024	Approved
0.6236	Remote Similarity	NPD1625	Approved
0.6228	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD3888	Discontinued
0.6224	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD7105	Phase 1
0.6209	Remote Similarity	NPD3372	Discontinued
0.6205	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD7600	Phase 2
0.6202	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD4121	Phase 3
0.6196	Remote Similarity	NPD4120	Approved
0.6196	Remote Similarity	NPD5086	Approved
0.6195	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8399	Phase 1
0.619	Remote Similarity	NPD8423	Phase 2
0.6185	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD6891	Phase 2
0.6175	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD1070	Approved
0.6163	Remote Similarity	NPD1069	Approved
0.6162	Remote Similarity	NPD5742	Approved
0.6162	Remote Similarity	NPD5743	Approved
0.6162	Remote Similarity	NPD5741	Approved
0.6158	Remote Similarity	NPD4602	Approved
0.6154	Remote Similarity	NPD4161	Discontinued
0.6154	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.615	Remote Similarity	NPD4393	Approved
0.615	Remote Similarity	NPD33	Approved
0.6145	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD7962	Phase 2
0.614	Remote Similarity	NPD766	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7569	Approved
0.6139	Remote Similarity	NPD7570	Approved
0.6134	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD5860	Discontinued
0.6129	Remote Similarity	NPD2836	Approved
0.6129	Remote Similarity	NPD1663	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