NPASS Compound

Structure

NPC469462 OpenBabel07101718202D 28 33 0 0 1 0 0 0 0 0999 V2000 1.3053 -2.2608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6686 -3.0725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0373 -1.2608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5488 0.1412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5506 0.8613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9243 -0.2173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9279 1.2229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1370 -0.1222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6418 0.1484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3053 -1.2608 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5432 -2.5876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0144 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.3016 0.1443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3034 0.8644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4751 0.5411 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1268 -0.7088 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4392 -0.7608 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7829 -1.4635 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.1944 0.5070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7034 -1.0728 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.4392 -0.2536 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6162 -0.0766 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6191 1.0886 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -3.4004 -3.1026 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3053 0.2464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1713 -0.7608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5606 -1.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 27 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 2 0 0 0 0 7 14 2 0 0 0 0 8 12 1 0 0 0 0 9 16 1 0 0 0 0 10 27 1 0 0 0 0 11 25 2 0 0 0 0 11 28 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 8 1 6 0 0 0 15 19 1 0 0 0 0 15 24 1 0 0 0 0 16 18 1 0 0 0 0 16 24 1 6 0 0 0 17 10 1 1 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 19 22 1 0 0 0 0 19 23 2 0 0 0 0 20 22 1 0 0 0 0 20 28 1 0 0 0 0 21 24 1 6 0 0 0 21 26 1 0 0 0 0 22 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.19
Volume:	381.702
LogP:	1.054
LogD:	1.292
LogS:	-2.482
# Rotatable Bonds:	4
TPSA:	71.36
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.81
Synthetic Accessibility Score:	6.69
Fsp3:	0.636
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:	-4.908
MDCK Permeability:	6.193660374265164e-05
Pgp-inhibitor:	0.437
Pgp-substrate:	0.811
Human Intestinal Absorption (HIA):	0.4
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.928

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.681
Plasma Protein Binding (PPB):	54.200958251953125%
Volume Distribution (VD):	3.258
Pgp-substrate:	46.397037506103516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.801
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.156
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.724
CYP3A4-inhibitor:	0.114
CYP3A4-substrate:	0.77

ADMET: Excretion

Clearance (CL):	4.901
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.9
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.427
Rat Oral Acute Toxicity:	0.773
Maximum Recommended Daily Dose:	0.911
Skin Sensitization:	0.119
Carcinogencity:	0.616
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC469462

Natural Product ID:	NPC469462
*Common Name:**	Alstoyunine F
IUPAC Name:	n.a.
Synonyms:	Alstoyunine F
Standard InCHIKey:	XHABFDBTVXEZFH-YNQCBNRXSA-N
Standard InCHI:	InChI=1S/C22H26N2O4/c1-10(27-3)17-12-8-15-19-22(13-6-4-5-7-14(13)23-19)9-16(24(15)21(17)26)18(12)20(22)28-11(2)25/h4-7,10,12,15-18,20-21,26H,8-9H2,1-3H3/t10?,12?,15-,16-,17-,18?,20?,21+,22+/m0/s1
SMILES:	CC(C1C2CC3C4=NC5=CC=CC=C5C46CC(C2C6OC(=O)C)N3C1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079305
PubChem CID:	46882339
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001794] Ajmaline-sarpagine 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
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19775092]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17362	Alstonia yunnanensis	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	2
Others	3

Activity Type	# Activity
Cell Line	2
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	39.82	%	PMID[569112]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	77.18	%	PMID[569112]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Inhibition	=	61.82	%	PMID[569112]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	3890.0	nM	PMID[569112]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	21730.0	nM	PMID[569112]

☑ 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 NPC469462 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	205
0.1-0.2	1088
0.2-0.3	2741
0.3-0.4	16202
0.4-0.5	16948
0.5-0.6	4591
0.6-0.7	823
0.7-0.8	87
0.8-0.85	8
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8981	High Similarity	NPC469461
0.881	High Similarity	NPC469460
0.8581	High Similarity	NPC472100
0.848	Intermediate Similarity	NPC472209
0.8176	Intermediate Similarity	NPC476441
0.816	Intermediate Similarity	NPC477157
0.816	Intermediate Similarity	NPC477156
0.8059	Intermediate Similarity	NPC476425
0.8012	Intermediate Similarity	NPC477158
0.7987	Intermediate Similarity	NPC472103
0.7953	Intermediate Similarity	NPC181138
0.7953	Intermediate Similarity	NPC21752
0.7953	Intermediate Similarity	NPC298851
0.7953	Intermediate Similarity	NPC210415
0.7953	Intermediate Similarity	NPC293255
0.7953	Intermediate Similarity	NPC276993
0.7886	Intermediate Similarity	NPC475962
0.7886	Intermediate Similarity	NPC476428
0.7784	Intermediate Similarity	NPC211525
0.7784	Intermediate Similarity	NPC153694
0.7738	Intermediate Similarity	NPC310403
0.7738	Intermediate Similarity	NPC148468
0.7738	Intermediate Similarity	NPC97380
0.7738	Intermediate Similarity	NPC63210
0.7738	Intermediate Similarity	NPC263709
0.7738	Intermediate Similarity	NPC243673
0.7714	Intermediate Similarity	NPC476326
0.7665	Intermediate Similarity	NPC473297
0.7661	Intermediate Similarity	NPC470069
0.7661	Intermediate Similarity	NPC52059
0.7625	Intermediate Similarity	NPC243162
0.7622	Intermediate Similarity	NPC475559
0.7607	Intermediate Similarity	NPC116519
0.756	Intermediate Similarity	NPC161827
0.75	Intermediate Similarity	NPC478076
0.7457	Intermediate Similarity	NPC472106
0.7433	Intermediate Similarity	NPC302548
0.7414	Intermediate Similarity	NPC278887
0.7341	Intermediate Similarity	NPC472121
0.7263	Intermediate Similarity	NPC24594
0.7263	Intermediate Similarity	NPC472122
0.7253	Intermediate Similarity	NPC472104
0.7241	Intermediate Similarity	NPC472101
0.7241	Intermediate Similarity	NPC472120
0.7238	Intermediate Similarity	NPC187827
0.7238	Intermediate Similarity	NPC472105
0.7228	Intermediate Similarity	NPC282092
0.7228	Intermediate Similarity	NPC291759
0.7207	Intermediate Similarity	NPC13367
0.7174	Intermediate Similarity	NPC133591
0.715	Intermediate Similarity	NPC474077
0.7135	Intermediate Similarity	NPC38823
0.7135	Intermediate Similarity	NPC207033
0.712	Intermediate Similarity	NPC245741
0.7086	Intermediate Similarity	NPC143457
0.7074	Intermediate Similarity	NPC28510
0.7065	Intermediate Similarity	NPC472110
0.7065	Intermediate Similarity	NPC139291
0.7065	Intermediate Similarity	NPC472109
0.7065	Intermediate Similarity	NPC472108
0.7047	Intermediate Similarity	NPC475489
0.7024	Intermediate Similarity	NPC106593
0.7022	Intermediate Similarity	NPC472114
0.7022	Intermediate Similarity	NPC472115
0.6995	Remote Similarity	NPC133261
0.699	Remote Similarity	NPC473667
0.6968	Remote Similarity	NPC217294
0.6927	Remote Similarity	NPC140311
0.6914	Remote Similarity	NPC29285
0.6911	Remote Similarity	NPC203972
0.6905	Remote Similarity	NPC477155
0.6895	Remote Similarity	NPC472097
0.6856	Remote Similarity	NPC52557
0.6854	Remote Similarity	NPC472117
0.6848	Remote Similarity	NPC326575
0.6811	Remote Similarity	NPC218594
0.6811	Remote Similarity	NPC99043
0.6802	Remote Similarity	NPC212799
0.6798	Remote Similarity	NPC472102
0.6798	Remote Similarity	NPC474058
0.6798	Remote Similarity	NPC309531
0.6791	Remote Similarity	NPC98197
0.676	Remote Similarity	NPC85651
0.6754	Remote Similarity	NPC469470
0.6754	Remote Similarity	NPC469501
0.6754	Remote Similarity	NPC22689
0.6754	Remote Similarity	NPC105055
0.6737	Remote Similarity	NPC472323
0.6728	Remote Similarity	NPC478079
0.6715	Remote Similarity	NPC223590
0.6708	Remote Similarity	NPC325013
0.6705	Remote Similarity	NPC476757
0.6704	Remote Similarity	NPC81229
0.6704	Remote Similarity	NPC255229
0.6702	Remote Similarity	NPC477159
0.6699	Remote Similarity	NPC473837
0.6686	Remote Similarity	NPC328824
0.6686	Remote Similarity	NPC475578
0.6685	Remote Similarity	NPC113946
0.6685	Remote Similarity	NPC472123
0.6667	Remote Similarity	NPC97584
0.6667	Remote Similarity	NPC472119
0.6667	Remote Similarity	NPC176983
0.6647	Remote Similarity	NPC264589
0.6646	Remote Similarity	NPC317758
0.6645	Remote Similarity	NPC470550
0.6635	Remote Similarity	NPC108826
0.6633	Remote Similarity	NPC90967
0.6632	Remote Similarity	NPC52262
0.6629	Remote Similarity	NPC217801
0.6617	Remote Similarity	NPC472111
0.6615	Remote Similarity	NPC57994
0.6615	Remote Similarity	NPC289299
0.6613	Remote Similarity	NPC203202
0.6613	Remote Similarity	NPC264482
0.6611	Remote Similarity	NPC225319
0.6604	Remote Similarity	NPC476436
0.6601	Remote Similarity	NPC168250
0.6596	Remote Similarity	NPC15840
0.6595	Remote Similarity	NPC473880
0.659	Remote Similarity	NPC477556
0.6587	Remote Similarity	NPC64897
0.6587	Remote Similarity	NPC90693
0.6582	Remote Similarity	NPC264580
0.6578	Remote Similarity	NPC186669
0.657	Remote Similarity	NPC473922
0.6554	Remote Similarity	NPC275839
0.6545	Remote Similarity	NPC79062
0.6545	Remote Similarity	NPC69496
0.6545	Remote Similarity	NPC62510
0.6545	Remote Similarity	NPC472107
0.6543	Remote Similarity	NPC6974
0.6538	Remote Similarity	NPC469541
0.6533	Remote Similarity	NPC195461
0.6533	Remote Similarity	NPC313985
0.6533	Remote Similarity	NPC249150
0.6533	Remote Similarity	NPC49196
0.6533	Remote Similarity	NPC81654
0.6533	Remote Similarity	NPC79129
0.6532	Remote Similarity	NPC311330
0.6528	Remote Similarity	NPC175474
0.6526	Remote Similarity	NPC159963
0.6526	Remote Similarity	NPC19679
0.6524	Remote Similarity	NPC203754
0.6524	Remote Similarity	NPC150048
0.6522	Remote Similarity	NPC317430
0.6508	Remote Similarity	NPC39822
0.65	Remote Similarity	NPC472330
0.65	Remote Similarity	NPC471512
0.65	Remote Similarity	NPC472329
0.6497	Remote Similarity	NPC475763
0.6485	Remote Similarity	NPC259098
0.6485	Remote Similarity	NPC197680
0.6484	Remote Similarity	NPC99632
0.6484	Remote Similarity	NPC282339
0.6484	Remote Similarity	NPC286871
0.6477	Remote Similarity	NPC14994
0.6476	Remote Similarity	NPC52254
0.6465	Remote Similarity	NPC272706
0.6465	Remote Similarity	NPC469736
0.6464	Remote Similarity	NPC235460
0.6462	Remote Similarity	NPC25401
0.6455	Remote Similarity	NPC203005
0.6452	Remote Similarity	NPC476429
0.6452	Remote Similarity	NPC473486
0.6452	Remote Similarity	NPC475316
0.6448	Remote Similarity	NPC313757
0.6447	Remote Similarity	NPC221687
0.644	Remote Similarity	NPC143533
0.6437	Remote Similarity	NPC262216
0.6436	Remote Similarity	NPC129624
0.6433	Remote Similarity	NPC205652
0.6432	Remote Similarity	NPC50503
0.6429	Remote Similarity	NPC233910
0.6429	Remote Similarity	NPC245836
0.6429	Remote Similarity	NPC204970
0.642	Remote Similarity	NPC213126
0.642	Remote Similarity	NPC291027
0.642	Remote Similarity	NPC317474
0.642	Remote Similarity	NPC84281
0.642	Remote Similarity	NPC169485
0.6417	Remote Similarity	NPC251212
0.6417	Remote Similarity	NPC214626
0.6417	Remote Similarity	NPC139085
0.6414	Remote Similarity	NPC231342
0.6413	Remote Similarity	NPC70172
0.6413	Remote Similarity	NPC475420
0.6412	Remote Similarity	NPC478140
0.641	Remote Similarity	NPC473298
0.641	Remote Similarity	NPC174629
0.6406	Remote Similarity	NPC470631
0.6406	Remote Similarity	NPC473781
0.6406	Remote Similarity	NPC472294
0.6406	Remote Similarity	NPC35390
0.6404	Remote Similarity	NPC14339
0.64	Remote Similarity	NPC44649
0.64	Remote Similarity	NPC237240
0.64	Remote Similarity	NPC31171
0.6398	Remote Similarity	NPC472118
0.6398	Remote Similarity	NPC37957

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 NPC469462 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	129
0.1-0.2	466
0.2-0.3	651
0.3-0.4	1588
0.4-0.5	4115
0.5-0.6	2046
0.6-0.7	149
0.7-0.8	1
0.8-0.85	1
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8375	Intermediate Similarity	NPD4120	Approved
0.8375	Intermediate Similarity	NPD4121	Phase 3
0.8323	Intermediate Similarity	NPD5741	Approved
0.8323	Intermediate Similarity	NPD5742	Approved
0.8323	Intermediate Similarity	NPD5743	Approved
0.7289	Intermediate Similarity	NPD5595	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2210	Approved
0.6859	Remote Similarity	NPD2212	Approved
0.6798	Remote Similarity	NPD7600	Phase 2
0.6791	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5185	Approved
0.6687	Remote Similarity	NPD5184	Approved
0.6687	Remote Similarity	NPD5182	Approved
0.6667	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7599	Phase 2
0.6615	Remote Similarity	NPD4602	Approved
0.6571	Remote Similarity	NPD4682	Phase 2
0.6545	Remote Similarity	NPD2613	Approved
0.6545	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD4601	Approved
0.6533	Remote Similarity	NPD4600	Approved
0.6532	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7522	Discontinued
0.65	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4951	Discontinued
0.6474	Remote Similarity	NPD3148	Approved
0.6474	Remote Similarity	NPD2658	Approved
0.6474	Remote Similarity	NPD2659	Approved
0.6474	Remote Similarity	NPD3150	Approved
0.6474	Remote Similarity	NPD3149	Approved
0.6474	Remote Similarity	NPD3147	Approved
0.6474	Remote Similarity	NPD6301	Phase 2
0.644	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4745	Approved
0.6429	Remote Similarity	NPD4746	Phase 3
0.6429	Remote Similarity	NPD2573	Approved
0.6429	Remote Similarity	NPD3087	Approved
0.6429	Remote Similarity	NPD3615	Approved
0.6429	Remote Similarity	NPD3090	Approved
0.6429	Remote Similarity	NPD3614	Approved
0.6429	Remote Similarity	NPD3616	Approved
0.6429	Remote Similarity	NPD2571	Approved
0.6429	Remote Similarity	NPD2566	Approved
0.6429	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2570	Approved
0.6429	Remote Similarity	NPD3089	Approved
0.6429	Remote Similarity	NPD2574	Discontinued
0.6429	Remote Similarity	NPD3088	Approved
0.6425	Remote Similarity	NPD5811	Approved
0.642	Remote Similarity	NPD2608	Approved
0.642	Remote Similarity	NPD3131	Approved
0.642	Remote Similarity	NPD4217	Approved
0.642	Remote Similarity	NPD2611	Approved
0.642	Remote Similarity	NPD2610	Approved
0.642	Remote Similarity	NPD2612	Approved
0.642	Remote Similarity	NPD3132	Approved
0.642	Remote Similarity	NPD4218	Approved
0.642	Remote Similarity	NPD2609	Approved
0.642	Remote Similarity	NPD4216	Approved
0.642	Remote Similarity	NPD4215	Approved
0.641	Remote Similarity	NPD1762	Approved
0.641	Remote Similarity	NPD1764	Approved
0.6407	Remote Similarity	NPD4738	Phase 2
0.64	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD7795	Phase 2
0.6392	Remote Similarity	NPD8020	Approved
0.6392	Remote Similarity	NPD8021	Approved
0.6386	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD4501	Approved
0.6368	Remote Similarity	NPD4500	Approved
0.6358	Remote Similarity	NPD6789	Approved
0.6354	Remote Similarity	NPD5596	Phase 2
0.6353	Remote Similarity	NPD4685	Phase 3
0.6353	Remote Similarity	NPD4684	Phase 3
0.6353	Remote Similarity	NPD4686	Approved
0.635	Remote Similarity	NPD7777	Approved
0.635	Remote Similarity	NPD53	Approved
0.635	Remote Similarity	NPD7778	Approved
0.6329	Remote Similarity	NPD5631	Phase 3
0.6313	Remote Similarity	NPD7606	Phase 3
0.6305	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD2622	Approved
0.627	Remote Similarity	NPD6635	Approved
0.6266	Remote Similarity	NPD23	Approved
0.6264	Remote Similarity	NPD7105	Phase 1
0.625	Remote Similarity	NPD2387	Approved
0.625	Remote Similarity	NPD6878	Phase 2
0.625	Remote Similarity	NPD6879	Phase 2
0.625	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD4033	Approved
0.6244	Remote Similarity	NPD4038	Approved
0.6244	Remote Similarity	NPD32	Approved
0.6244	Remote Similarity	NPD4035	Approved
0.6244	Remote Similarity	NPD4122	Approved
0.6244	Remote Similarity	NPD4037	Approved
0.6244	Remote Similarity	NPD4499	Approved
0.6244	Remote Similarity	NPD31	Approved
0.6244	Remote Similarity	NPD4039	Approved
0.6244	Remote Similarity	NPD4034	Approved
0.6244	Remote Similarity	NPD4036	Approved
0.6238	Remote Similarity	NPD6874	Approved
0.6237	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD5706	Approved
0.6234	Remote Similarity	NPD5705	Approved
0.6234	Remote Similarity	NPD5704	Approved
0.623	Remote Similarity	NPD6694	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6641	Approved
0.623	Remote Similarity	NPD6642	Approved
0.6215	Remote Similarity	NPD7295	Approved
0.6214	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD8417	Discontinued
0.6209	Remote Similarity	NPD7463	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4707	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD4520	Approved
0.62	Remote Similarity	NPD4427	Phase 2
0.6188	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7962	Phase 2
0.6175	Remote Similarity	NPD6913	Approved
0.6171	Remote Similarity	NPD2093	Discontinued
0.6168	Remote Similarity	NPD7168	Phase 3
0.6167	Remote Similarity	NPD6222	Approved
0.6167	Remote Similarity	NPD6221	Approved
0.6166	Remote Similarity	NPD5899	Approved
0.6166	Remote Similarity	NPD5898	Approved
0.6166	Remote Similarity	NPD5897	Approved
0.6162	Remote Similarity	NPD8063	Discontinued
0.6162	Remote Similarity	NPD5989	Phase 1
0.6158	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD7487	Discontinued
0.6154	Remote Similarity	NPD2678	Approved
0.6154	Remote Similarity	NPD2679	Approved
0.615	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.615	Remote Similarity	NPD8325	Phase 3
0.615	Remote Similarity	NPD8326	Phase 3
0.6149	Remote Similarity	NPD3648	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD7478	Approved
0.6145	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.614	Remote Similarity	NPD8118	Discontinued
0.6138	Remote Similarity	NPD7474	Suspended
0.6134	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD8323	Discontinued
0.6122	Remote Similarity	NPD6227	Discontinued
0.6118	Remote Similarity	NPD4274	Approved
0.6118	Remote Similarity	NPD4275	Approved
0.6118	Remote Similarity	NPD3720	Discontinued
0.6114	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4703	Approved
0.6111	Remote Similarity	NPD4702	Approved
0.6108	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD5578	Approved
0.6105	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD7200	Approved
0.6105	Remote Similarity	NPD2216	Approved
0.6105	Remote Similarity	NPD6346	Approved
0.6105	Remote Similarity	NPD2215	Approved
0.6099	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD6158	Phase 2
0.6095	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD2381	Approved
0.6094	Remote Similarity	NPD2382	Approved
0.6094	Remote Similarity	NPD2380	Approved
0.6094	Remote Similarity	NPD5104	Approved
0.609	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6026	Approved
0.6085	Remote Similarity	NPD5862	Discovery
0.6085	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD7890	Discontinued
0.6085	Remote Similarity	NPD2844	Phase 3
0.6084	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.608	Remote Similarity	NPD2845	Phase 2
0.608	Remote Similarity	NPD2843	Phase 2
0.6073	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD7418	Discontinued
0.6073	Remote Similarity	NPD43	Approved
0.6073	Remote Similarity	NPD6182	Approved
0.6066	Remote Similarity	NPD1634	Approved
0.6064	Remote Similarity	NPD7035	Approved
0.6064	Remote Similarity	NPD7036	Phase 3
0.6061	Remote Similarity	NPD5576	Approved
0.6061	Remote Similarity	NPD5579	Approved
0.6059	Remote Similarity	NPD4365	Phase 2
0.6056	Remote Similarity	NPD6378	Approved
0.6054	Remote Similarity	NPD6885	Approved
0.6054	Remote Similarity	NPD6886	Approved
0.6047	Remote Similarity	NPD7715	Approved
0.6047	Remote Similarity	NPD7714	Approved
0.6044	Remote Similarity	NPD5982	Phase 2
0.6043	Remote Similarity	NPD2995	Approved

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