NPASS Compound

Structure

CID309531 OpenBabel06191716122D 24 27 0 0 1 0 0 0 0 0999 V2000 5.9944 -2.5326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5992 0.7398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3458 -2.8211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1443 -2.3026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5024 -2.3888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0946 -1.3519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3320 -2.1793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6324 -2.1793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6512 -0.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3320 -0.2168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2652 -1.8760 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4822 -1.6886 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4822 -0.7074 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5522 -1.4381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6324 -0.2168 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2463 -0.9196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7826 -1.6887 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9507 0.0499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2920 -0.8389 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7827 -0.7074 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.1712 0.7512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4692 -0.9162 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4692 0.8484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 21 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 16 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 8 17 1 0 0 0 0 10 22 1 0 0 0 0 11 1 1 1 0 0 0 11 23 1 0 0 0 0 12 7 1 6 0 0 0 12 13 1 0 0 0 0 13 10 1 6 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 15 9 1 1 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 19 1 1 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 18 24 2 0 0 0 0 19 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.19
Volume:	340.773
LogP:	0.856
LogD:	1.514
LogS:	-1.32
# Rotatable Bonds:	3
TPSA:	72.8
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.774
Synthetic Accessibility Score:	5.681
Fsp3:	0.632
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:	-5.582
MDCK Permeability:	9.78343541646609e-06
Pgp-inhibitor:	0.042
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.896
20% Bioavailability (F20%):	0.582
30% Bioavailability (F30%):	0.269

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.423
Plasma Protein Binding (PPB):	15.964421272277832%
Volume Distribution (VD):	1.593
Pgp-substrate:	77.9516372680664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.41
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.121
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.29
CYP3A4-inhibitor:	0.064
CYP3A4-substrate:	0.868

ADMET: Excretion

Clearance (CL):	8.821
Half-life (T1/2):	0.145

ADMET: Toxicity

hERG Blockers:	0.11
Human Hepatotoxicity (H-HT):	0.594
Drug-inuced Liver Injury (DILI):	0.064
AMES Toxicity:	0.268
Rat Oral Acute Toxicity:	0.256
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.735
Carcinogencity:	0.835
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC309531

Natural Product ID:	NPC309531
*Common Name:**	XPPHWJNQDGTLDY-TZWUEZEISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XPPHWJNQDGTLDY-TZWUEZEISA-N
Standard InCHI:	InChI=1S/C19H26N2O3/c1-11(23)7-12-8-17-19(9-15(20-17)13(12)10-22)14-5-3-4-6-16(14)21(2)18(19)24/h3-6,11-13,15,17,20,22-23H,7-10H2,1-2H3/p+1/t11-,12+,13+,15-,17-,19-/m0/s1
SMILES:	C[C@@H](C[C@@H]1C[C@H]2[C@]3(C[C@@H]([C@@H]1CO)[NH2+]2)c1ccccc1N(C)C3=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338250
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0001878] Beta amino acids 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
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19191551]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	leaves	Purwodadi Botanical Garden, Indonesia	n.a.	PMID[20189404]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[22148233]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	Barks	n.a.	n.a.	PMID[23806072]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	bark and leaf	Pahang, Malaysia	n.a.	PMID[25211145]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19678	Alstonia macrophylla	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

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[471383]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[471383]

☑ 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 NPC309531 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	192
0.1-0.2	960
0.2-0.3	3469
0.3-0.4	21365
0.4-0.5	11552
0.5-0.6	3892
0.6-0.7	1077
0.7-0.8	170
0.8-0.85	11
0.85-0.9	4
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472102
0.9281	High Similarity	NPC472120
0.9281	High Similarity	NPC472101
0.9281	High Similarity	NPC472117
0.9038	High Similarity	NPC472106
0.8861	High Similarity	NPC214960
0.8861	High Similarity	NPC279527
0.8599	High Similarity	NPC113946
0.8553	High Similarity	NPC286871
0.8405	Intermediate Similarity	NPC472118
0.8323	Intermediate Similarity	NPC176983
0.8258	Intermediate Similarity	NPC264589
0.8214	Intermediate Similarity	NPC218594
0.8214	Intermediate Similarity	NPC99043
0.8084	Intermediate Similarity	NPC285622
0.8075	Intermediate Similarity	NPC29285
0.807	Intermediate Similarity	NPC477159
0.805	Intermediate Similarity	NPC475763
0.8013	Intermediate Similarity	NPC472103
0.7988	Intermediate Similarity	NPC282339
0.7988	Intermediate Similarity	NPC203202
0.7988	Intermediate Similarity	NPC99632
0.7988	Intermediate Similarity	NPC264482
0.7975	Intermediate Similarity	NPC36495
0.7919	Intermediate Similarity	NPC97584
0.7818	Intermediate Similarity	NPC68650
0.7818	Intermediate Similarity	NPC315368
0.7818	Intermediate Similarity	NPC225319
0.7791	Intermediate Similarity	NPC475094
0.7791	Intermediate Similarity	NPC6974
0.7771	Intermediate Similarity	NPC52262
0.7765	Intermediate Similarity	NPC251212
0.7765	Intermediate Similarity	NPC139085
0.7765	Intermediate Similarity	NPC214626
0.7758	Intermediate Similarity	NPC193410
0.7756	Intermediate Similarity	NPC315051
0.774	Intermediate Similarity	NPC284706
0.7711	Intermediate Similarity	NPC248117
0.7697	Intermediate Similarity	NPC61013
0.7697	Intermediate Similarity	NPC22689
0.7697	Intermediate Similarity	NPC105055
0.7692	Intermediate Similarity	NPC167724
0.7692	Intermediate Similarity	NPC100863
0.7692	Intermediate Similarity	NPC223595
0.7692	Intermediate Similarity	NPC224970
0.7665	Intermediate Similarity	NPC472121
0.7661	Intermediate Similarity	NPC96901
0.7657	Intermediate Similarity	NPC159963
0.763	Intermediate Similarity	NPC186669
0.7609	Intermediate Similarity	NPC475489
0.7605	Intermediate Similarity	NPC143457
0.7595	Intermediate Similarity	NPC186284
0.7595	Intermediate Similarity	NPC22082
0.7584	Intermediate Similarity	NPC14994
0.7572	Intermediate Similarity	NPC129624
0.7572	Intermediate Similarity	NPC476441
0.756	Intermediate Similarity	NPC293458
0.7531	Intermediate Similarity	NPC212799
0.7529	Intermediate Similarity	NPC260075
0.7515	Intermediate Similarity	NPC478076
0.75	Intermediate Similarity	NPC355
0.7485	Intermediate Similarity	NPC123241
0.7472	Intermediate Similarity	NPC259626
0.7471	Intermediate Similarity	NPC471124
0.7469	Intermediate Similarity	NPC472100
0.7459	Intermediate Similarity	NPC25401
0.7443	Intermediate Similarity	NPC11149
0.744	Intermediate Similarity	NPC471122
0.7439	Intermediate Similarity	NPC318086
0.7432	Intermediate Similarity	NPC243626
0.7421	Intermediate Similarity	NPC130251
0.7416	Intermediate Similarity	NPC245741
0.7416	Intermediate Similarity	NPC2933
0.7414	Intermediate Similarity	NPC475097
0.7403	Intermediate Similarity	NPC473298
0.7396	Intermediate Similarity	NPC474058
0.7396	Intermediate Similarity	NPC201424
0.7381	Intermediate Similarity	NPC222029
0.736	Intermediate Similarity	NPC256288
0.7351	Intermediate Similarity	NPC90967
0.7346	Intermediate Similarity	NPC311330
0.7342	Intermediate Similarity	NPC471123
0.7337	Intermediate Similarity	NPC221687
0.7314	Intermediate Similarity	NPC469726
0.7314	Intermediate Similarity	NPC329338
0.7314	Intermediate Similarity	NPC13367
0.7302	Intermediate Similarity	NPC477179
0.7293	Intermediate Similarity	NPC181928
0.7292	Intermediate Similarity	NPC477160
0.7287	Intermediate Similarity	NPC471512
0.7278	Intermediate Similarity	NPC153694
0.7278	Intermediate Similarity	NPC211525
0.7267	Intermediate Similarity	NPC52059
0.7267	Intermediate Similarity	NPC470069
0.7263	Intermediate Similarity	NPC477180
0.7263	Intermediate Similarity	NPC477181
0.7263	Intermediate Similarity	NPC254850
0.7263	Intermediate Similarity	NPC477178
0.7258	Intermediate Similarity	NPC302548
0.7257	Intermediate Similarity	NPC181138
0.7257	Intermediate Similarity	NPC21752
0.7257	Intermediate Similarity	NPC476425
0.7257	Intermediate Similarity	NPC276993
0.7257	Intermediate Similarity	NPC210415
0.7257	Intermediate Similarity	NPC293255
0.7257	Intermediate Similarity	NPC177261
0.7257	Intermediate Similarity	NPC298851
0.7243	Intermediate Similarity	NPC230313
0.724	Intermediate Similarity	NPC471945
0.724	Intermediate Similarity	NPC471950
0.7238	Intermediate Similarity	NPC282092
0.7238	Intermediate Similarity	NPC473615
0.7235	Intermediate Similarity	NPC276085
0.7235	Intermediate Similarity	NPC63210
0.7235	Intermediate Similarity	NPC97380
0.7235	Intermediate Similarity	NPC243673
0.7235	Intermediate Similarity	NPC148468
0.7235	Intermediate Similarity	NPC310403
0.7235	Intermediate Similarity	NPC263709
0.7225	Intermediate Similarity	NPC477173
0.7225	Intermediate Similarity	NPC470490
0.7225	Intermediate Similarity	NPC477174
0.7209	Intermediate Similarity	NPC113056
0.7209	Intermediate Similarity	NPC138293
0.7207	Intermediate Similarity	NPC476428
0.7202	Intermediate Similarity	NPC471951
0.7202	Intermediate Similarity	NPC471946
0.7198	Intermediate Similarity	NPC229484
0.7188	Intermediate Similarity	NPC470488
0.7186	Intermediate Similarity	NPC66936
0.7186	Intermediate Similarity	NPC154602
0.7182	Intermediate Similarity	NPC473007
0.7182	Intermediate Similarity	NPC307396
0.7166	Intermediate Similarity	NPC162440
0.7166	Intermediate Similarity	NPC475559
0.7165	Intermediate Similarity	NPC475359
0.7165	Intermediate Similarity	NPC191817
0.716	Intermediate Similarity	NPC301760
0.7159	Intermediate Similarity	NPC473743
0.7158	Intermediate Similarity	NPC1464
0.7158	Intermediate Similarity	NPC292675
0.7151	Intermediate Similarity	NPC85651
0.715	Intermediate Similarity	NPC475259
0.715	Intermediate Similarity	NPC470491
0.7126	Intermediate Similarity	NPC472115
0.7126	Intermediate Similarity	NPC472114
0.7119	Intermediate Similarity	NPC470548
0.7112	Intermediate Similarity	NPC473375
0.7112	Intermediate Similarity	NPC97100
0.711	Intermediate Similarity	NPC313757
0.7107	Intermediate Similarity	NPC162417
0.7107	Intermediate Similarity	NPC316104
0.7099	Intermediate Similarity	NPC243162
0.7097	Intermediate Similarity	NPC470485
0.709	Intermediate Similarity	NPC106118
0.7086	Intermediate Similarity	NPC33507
0.7083	Intermediate Similarity	NPC329833
0.7083	Intermediate Similarity	NPC470489
0.7083	Intermediate Similarity	NPC87714
0.7081	Intermediate Similarity	NPC203628
0.7073	Intermediate Similarity	NPC469537
0.7059	Intermediate Similarity	NPC161827
0.7059	Intermediate Similarity	NPC34717
0.7052	Intermediate Similarity	NPC469741
0.7047	Intermediate Similarity	NPC246140
0.7047	Intermediate Similarity	NPC195787
0.7045	Intermediate Similarity	NPC469915
0.7043	Intermediate Similarity	NPC473004
0.7037	Intermediate Similarity	NPC469560
0.7027	Intermediate Similarity	NPC5630
0.7027	Intermediate Similarity	NPC473008
0.7024	Intermediate Similarity	NPC473329
0.6989	Remote Similarity	NPC276430
0.6989	Remote Similarity	NPC470483
0.6982	Remote Similarity	NPC243756
0.6979	Remote Similarity	NPC471436
0.6964	Remote Similarity	NPC109787
0.6963	Remote Similarity	NPC138830
0.6963	Remote Similarity	NPC67904
0.6961	Remote Similarity	NPC286994
0.6961	Remote Similarity	NPC15840
0.6951	Remote Similarity	NPC471164
0.6951	Remote Similarity	NPC470301
0.6947	Remote Similarity	NPC52557
0.6944	Remote Similarity	NPC476326
0.6944	Remote Similarity	NPC64436
0.6941	Remote Similarity	NPC285381
0.6935	Remote Similarity	NPC189661
0.6935	Remote Similarity	NPC128582
0.6931	Remote Similarity	NPC303214
0.6923	Remote Similarity	NPC472538
0.6885	Remote Similarity	NPC472109
0.6885	Remote Similarity	NPC472110
0.6879	Remote Similarity	NPC104345
0.6879	Remote Similarity	NPC469428
0.6872	Remote Similarity	NPC225400
0.6872	Remote Similarity	NPC473880
0.6872	Remote Similarity	NPC242269
0.6868	Remote Similarity	NPC91179
0.6859	Remote Similarity	NPC265642

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 NPC309531 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	137
0.1-0.2	416
0.2-0.3	647
0.3-0.4	1451
0.4-0.5	3284
0.5-0.6	2626
0.6-0.7	566
0.7-0.8	23
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
0.7622	Intermediate Similarity	NPD4120	Approved
0.7622	Intermediate Similarity	NPD4121	Phase 3
0.7576	Intermediate Similarity	NPD5741	Approved
0.7576	Intermediate Similarity	NPD5743	Approved
0.7576	Intermediate Similarity	NPD5742	Approved
0.7484	Intermediate Similarity	NPD3625	Discontinued
0.7381	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5024	Approved
0.7273	Intermediate Similarity	NPD5941	Approved
0.7273	Intermediate Similarity	NPD5942	Approved
0.7219	Intermediate Similarity	NPD1663	Discontinued
0.7209	Intermediate Similarity	NPD3790	Phase 2
0.7178	Intermediate Similarity	NPD2820	Phase 3
0.7135	Intermediate Similarity	NPD4393	Approved
0.7135	Intermediate Similarity	NPD33	Approved
0.7125	Intermediate Similarity	NPD6102	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2365	Approved
0.7093	Intermediate Similarity	NPD7600	Phase 2
0.7059	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7599	Phase 2
0.7013	Intermediate Similarity	NPD3622	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3623	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5727	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5184	Approved
0.7	Intermediate Similarity	NPD5182	Approved
0.7	Intermediate Similarity	NPD5185	Approved
0.6989	Remote Similarity	NPD8240	Discontinued
0.6977	Remote Similarity	NPD8630	Approved
0.6975	Remote Similarity	NPD6358	Phase 2
0.6954	Remote Similarity	NPD2638	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6792	Phase 3
0.6919	Remote Similarity	NPD7105	Phase 1
0.6902	Remote Similarity	NPD6557	Phase 2
0.6901	Remote Similarity	NPD2790	Discontinued
0.6864	Remote Similarity	NPD4682	Phase 2
0.6864	Remote Similarity	NPD979	Approved
0.6848	Remote Similarity	NPD2093	Discontinued
0.6845	Remote Similarity	NPD4499	Approved
0.6826	Remote Similarity	NPD5918	Discontinued
0.6815	Remote Similarity	NPD1036	Approved
0.6807	Remote Similarity	NPD6768	Approved
0.68	Remote Similarity	NPD5181	Approved
0.68	Remote Similarity	NPD5180	Approved
0.68	Remote Similarity	NPD5179	Approved
0.6796	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7295	Approved
0.6776	Remote Similarity	NPD6878	Phase 2
0.6776	Remote Similarity	NPD6879	Phase 2
0.6768	Remote Similarity	NPD6342	Discontinued
0.6766	Remote Similarity	NPD4430	Phase 2
0.675	Remote Similarity	NPD5263	Approved
0.6748	Remote Similarity	NPD2791	Discontinued
0.6742	Remote Similarity	NPD5823	Approved
0.6736	Remote Similarity	NPD7308	Discontinued
0.6725	Remote Similarity	NPD5748	Phase 2
0.6725	Remote Similarity	NPD1405	Approved
0.6724	Remote Similarity	NPD951	Approved
0.6708	Remote Similarity	NPD1069	Approved
0.6708	Remote Similarity	NPD1070	Approved
0.6707	Remote Similarity	NPD6073	Approved
0.6704	Remote Similarity	NPD2037	Approved
0.6701	Remote Similarity	NPD4600	Approved
0.6701	Remote Similarity	NPD4601	Approved
0.6686	Remote Similarity	NPD5060	Phase 1
0.6686	Remote Similarity	NPD5931	Phase 3
0.6686	Remote Similarity	NPD5933	Phase 3
0.6686	Remote Similarity	NPD5932	Phase 3
0.6686	Remote Similarity	NPD6017	Discontinued
0.6685	Remote Similarity	NPD5997	Discontinued
0.6685	Remote Similarity	NPD4329	Approved
0.6685	Remote Similarity	NPD4330	Approved
0.6667	Remote Similarity	NPD5581	Approved
0.6667	Remote Similarity	NPD5186	Approved
0.6667	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6294	Approved
0.6667	Remote Similarity	NPD7072	Phase 2
0.6667	Remote Similarity	NPD3449	Discontinued
0.6667	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5183	Approved
0.6667	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7795	Phase 2
0.6667	Remote Similarity	NPD6295	Approved
0.6667	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.665	Remote Similarity	NPD5426	Phase 3
0.665	Remote Similarity	NPD8114	Approved
0.665	Remote Similarity	NPD8115	Approved
0.6649	Remote Similarity	NPD3470	Approved
0.6649	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3471	Approved
0.6649	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6891	Phase 2
0.6647	Remote Similarity	NPD3141	Discontinued
0.6646	Remote Similarity	NPD5131	Approved
0.6646	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4676	Approved
0.663	Remote Similarity	NPD2431	Approved
0.663	Remote Similarity	NPD2432	Approved
0.6629	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6395	Phase 2
0.6627	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7487	Discontinued
0.6624	Remote Similarity	NPD4215	Approved
0.6624	Remote Similarity	NPD3131	Approved
0.6624	Remote Similarity	NPD2610	Approved
0.6624	Remote Similarity	NPD2609	Approved
0.6624	Remote Similarity	NPD4217	Approved
0.6624	Remote Similarity	NPD3132	Approved
0.6624	Remote Similarity	NPD2611	Approved
0.6624	Remote Similarity	NPD2612	Approved
0.6624	Remote Similarity	NPD4218	Approved
0.6624	Remote Similarity	NPD2608	Approved
0.6624	Remote Similarity	NPD4216	Approved
0.6615	Remote Similarity	NPD6805	Discontinued
0.6611	Remote Similarity	NPD2454	Approved
0.6611	Remote Similarity	NPD2455	Approved
0.661	Remote Similarity	NPD2511	Approved
0.6609	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6566	Discontinued
0.6606	Remote Similarity	NPD5725	Approved
0.6591	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4177	Approved
0.6584	Remote Similarity	NPD4175	Approved
0.6584	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD3072	Approved
0.6582	Remote Similarity	NPD6238	Discontinued
0.6582	Remote Similarity	NPD3073	Approved
0.6582	Remote Similarity	NPD3071	Approved
0.6582	Remote Similarity	NPD7817	Phase 1
0.6576	Remote Similarity	NPD3792	Approved
0.6568	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD7082	Approved
0.6561	Remote Similarity	NPD6483	Approved
0.6561	Remote Similarity	NPD6484	Approved
0.6557	Remote Similarity	NPD3423	Phase 2
0.6557	Remote Similarity	NPD3422	Phase 3
0.6554	Remote Similarity	NPD4514	Approved
0.6545	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5076	Approved
0.6545	Remote Similarity	NPD5077	Approved
0.6545	Remote Similarity	NPD5042	Phase 1
0.6543	Remote Similarity	NPD2613	Approved
0.6541	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6995	Phase 1
0.6538	Remote Similarity	NPD3824	Phase 1
0.6531	Remote Similarity	NPD4500	Approved
0.6531	Remote Similarity	NPD4501	Approved
0.6529	Remote Similarity	NPD7259	Approved
0.6528	Remote Similarity	NPD7944	Discontinued
0.6527	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7086	Phase 2
0.6522	Remote Similarity	NPD5993	Phase 1
0.6519	Remote Similarity	NPD4762	Approved
0.6519	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD2404	Discontinued
0.6519	Remote Similarity	NPD4761	Approved
0.6517	Remote Similarity	NPD5992	Approved
0.6514	Remote Similarity	NPD5086	Approved
0.6512	Remote Similarity	NPD7088	Discontinued
0.6506	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7878	Phase 2
0.6503	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5578	Approved
0.65	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8322	Phase 2
0.65	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD5982	Phase 2
0.6491	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4549	Discontinued
0.6481	Remote Similarity	NPD1781	Discontinued
0.6478	Remote Similarity	NPD1360	Approved
0.6478	Remote Similarity	NPD519	Approved
0.6477	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4432	Discontinued
0.6474	Remote Similarity	NPD6345	Approved
0.6474	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6343	Approved
0.6474	Remote Similarity	NPD4942	Approved
0.6474	Remote Similarity	NPD2994	Approved
0.6471	Remote Similarity	NPD1374	Approved
0.6471	Remote Similarity	NPD1370	Approved
0.6471	Remote Similarity	NPD1371	Approved
0.6471	Remote Similarity	NPD1373	Approved
0.6471	Remote Similarity	NPD6301	Phase 2
0.6467	Remote Similarity	NPD5318	Discontinued
0.6467	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD3828	Approved
0.6458	Remote Similarity	NPD5504	Discontinued
0.6458	Remote Similarity	NPD6659	Phase 2
0.6457	Remote Similarity	NPD8401	Approved
0.6457	Remote Similarity	NPD8402	Approved
0.6457	Remote Similarity	NPD8400	Approved
0.6456	Remote Similarity	NPD1124	Approved
0.6456	Remote Similarity	NPD1123	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