NPASS Compound

Structure

NPC472103 OpenBabel07101718242D 23 26 0 0 1 0 0 0 0 0999 V2000 -2.4700 -3.8372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7572 -2.6783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3968 -2.1371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1444 -0.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3593 -1.2090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4481 -3.6293 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0880 -1.9351 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3611 -1.2688 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0104 -0.6399 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8080 -1.7226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8025 -1.6180 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 -4.9102 -2.0436 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1173 -4.3725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 13 2 0 0 0 0 5 14 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 7 16 1 0 0 0 0 9 21 1 0 0 0 0 10 1 1 6 0 0 0 10 22 1 0 0 0 0 11 6 1 1 0 0 0 11 12 1 0 0 0 0 12 9 1 1 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 8 1 6 0 0 0 15 19 1 0 0 0 0 16 18 1 6 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 17 23 1 0 0 0 0 18 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.18
Volume:	323.477
LogP:	0.66
LogD:	1.601
LogS:	-1.654
# Rotatable Bonds:	3
TPSA:	81.59
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.671
Synthetic Accessibility Score:	5.712
Fsp3:	0.611
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:	-5.648
MDCK Permeability:	7.233425549202366e-06
Pgp-inhibitor:	0.009
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.765
20% Bioavailability (F20%):	0.137
30% Bioavailability (F30%):	0.144

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.354
Plasma Protein Binding (PPB):	13.28318977355957%
Volume Distribution (VD):	1.181
Pgp-substrate:	75.22323608398438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.348
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.856
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.103
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.274
CYP3A4-inhibitor:	0.065
CYP3A4-substrate:	0.61

ADMET: Excretion

Clearance (CL):	10.281
Half-life (T1/2):	0.344

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.699
Drug-inuced Liver Injury (DILI):	0.081
AMES Toxicity:	0.47
Rat Oral Acute Toxicity:	0.384
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.852
Carcinogencity:	0.843
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC472103

Natural Product ID:	NPC472103
*Common Name:**	ZPMZMDMYYCLKMQ-NVMBSAOKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZPMZMDMYYCLKMQ-NVMBSAOKSA-N
Standard InCHI:	InChI=1S/C18H24N2O3/c1-10(22)6-11-7-16-18(8-15(19-16)12(11)9-21)13-4-2-3-5-14(13)20-17(18)23/h2-5,10-12,15-16,19,21-22H,6-9H2,1H3,(H,20,23)/t10-,11+,12+,15-,16-,18-/m0/s1
SMILES:	OC[C@@H]1[C@H](C[C@@H](O)C)C[C@@H]2N[C@H]1C[C@]12C(=Nc2c1cccc2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338226
PubChem CID:	n.a.
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
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	bark and leaf	Pahang, Malaysia	n.a.	PMID[25211145]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28762	Alstonia angustifolia	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[510309]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[510309]

☑ 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 NPC472103 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	194
0.1-0.2	966
0.2-0.3	4149
0.3-0.4	20977
0.4-0.5	10683
0.5-0.6	4557
0.6-0.7	1076
0.7-0.8	85
0.8-0.85	6
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9149	High Similarity	NPC472100
0.8553	High Similarity	NPC472121
0.8333	Intermediate Similarity	NPC243162
0.8052	Intermediate Similarity	NPC477157
0.8052	Intermediate Similarity	NPC477156
0.8013	Intermediate Similarity	NPC472102
0.8013	Intermediate Similarity	NPC309531
0.8	Intermediate Similarity	NPC211525
0.8	Intermediate Similarity	NPC264589
0.8	Intermediate Similarity	NPC153694
0.7987	Intermediate Similarity	NPC469462
0.795	Intermediate Similarity	NPC181138
0.795	Intermediate Similarity	NPC21752
0.795	Intermediate Similarity	NPC276993
0.795	Intermediate Similarity	NPC298851
0.795	Intermediate Similarity	NPC293255
0.795	Intermediate Similarity	NPC210415
0.7949	Intermediate Similarity	NPC148468
0.7949	Intermediate Similarity	NPC243673
0.7949	Intermediate Similarity	NPC310403
0.7949	Intermediate Similarity	NPC263709
0.7949	Intermediate Similarity	NPC97380
0.7949	Intermediate Similarity	NPC63210
0.7862	Intermediate Similarity	NPC470069
0.7862	Intermediate Similarity	NPC52059
0.7792	Intermediate Similarity	NPC475763
0.7756	Intermediate Similarity	NPC161827
0.7673	Intermediate Similarity	NPC477158
0.7647	Intermediate Similarity	NPC470550
0.7582	Intermediate Similarity	NPC116519
0.7516	Intermediate Similarity	NPC176983
0.7516	Intermediate Similarity	NPC286871
0.7516	Intermediate Similarity	NPC311330
0.7453	Intermediate Similarity	NPC143457
0.7448	Intermediate Similarity	NPC478079
0.7412	Intermediate Similarity	NPC19679
0.7407	Intermediate Similarity	NPC472120
0.7407	Intermediate Similarity	NPC472101
0.7407	Intermediate Similarity	NPC85651
0.7407	Intermediate Similarity	NPC472117
0.7391	Intermediate Similarity	NPC205652
0.7391	Intermediate Similarity	NPC469461
0.7353	Intermediate Similarity	NPC475962
0.731	Intermediate Similarity	NPC477159
0.731	Intermediate Similarity	NPC472110
0.731	Intermediate Similarity	NPC472109
0.731	Intermediate Similarity	NPC325013
0.7305	Intermediate Similarity	NPC264580
0.7278	Intermediate Similarity	NPC318086
0.7273	Intermediate Similarity	NPC278887
0.7267	Intermediate Similarity	NPC245741
0.7239	Intermediate Similarity	NPC68650
0.7235	Intermediate Similarity	NPC99043
0.7235	Intermediate Similarity	NPC218594
0.7229	Intermediate Similarity	NPC317430
0.7212	Intermediate Similarity	NPC472106
0.7209	Intermediate Similarity	NPC139291
0.7209	Intermediate Similarity	NPC472108
0.716	Intermediate Similarity	NPC29285
0.716	Intermediate Similarity	NPC475097
0.716	Intermediate Similarity	NPC13367
0.716	Intermediate Similarity	NPC329688
0.716	Intermediate Similarity	NPC189812
0.7126	Intermediate Similarity	NPC469460
0.7118	Intermediate Similarity	NPC476441
0.7101	Intermediate Similarity	NPC472123
0.7092	Intermediate Similarity	NPC101139
0.7086	Intermediate Similarity	NPC282092
0.7083	Intermediate Similarity	NPC472118
0.7076	Intermediate Similarity	NPC326575
0.7069	Intermediate Similarity	NPC472294
0.7066	Intermediate Similarity	NPC279527
0.7066	Intermediate Similarity	NPC214960
0.7062	Intermediate Similarity	NPC95783
0.7059	Intermediate Similarity	NPC472586
0.7055	Intermediate Similarity	NPC285469
0.7051	Intermediate Similarity	NPC477155
0.7042	Intermediate Similarity	NPC147957
0.7035	Intermediate Similarity	NPC472443
0.7035	Intermediate Similarity	NPC133261
0.702	Intermediate Similarity	NPC476689
0.702	Intermediate Similarity	NPC476685
0.702	Intermediate Similarity	NPC476687
0.7018	Intermediate Similarity	NPC472122
0.7018	Intermediate Similarity	NPC24594
0.7018	Intermediate Similarity	NPC264482
0.7018	Intermediate Similarity	NPC203202
0.7017	Intermediate Similarity	NPC475559
0.7017	Intermediate Similarity	NPC302548
0.7012	Intermediate Similarity	NPC469428
0.7006	Intermediate Similarity	NPC217294
0.7006	Intermediate Similarity	NPC284706
0.7	Intermediate Similarity	NPC34508
0.6971	Remote Similarity	NPC97584
0.697	Remote Similarity	NPC36495
0.6963	Remote Similarity	NPC178681
0.6941	Remote Similarity	NPC158129
0.6937	Remote Similarity	NPC212799
0.6933	Remote Similarity	NPC197680
0.6933	Remote Similarity	NPC259098
0.6932	Remote Similarity	NPC163421
0.6932	Remote Similarity	NPC188387
0.6914	Remote Similarity	NPC472444
0.6914	Remote Similarity	NPC98197
0.6897	Remote Similarity	NPC472105
0.6897	Remote Similarity	NPC39822
0.6897	Remote Similarity	NPC187827
0.6887	Remote Similarity	NPC226662
0.6886	Remote Similarity	NPC16667
0.6886	Remote Similarity	NPC99632
0.6886	Remote Similarity	NPC282339
0.6839	Remote Similarity	NPC6974
0.6839	Remote Similarity	NPC270009
0.6836	Remote Similarity	NPC52262
0.6836	Remote Similarity	NPC472209
0.6826	Remote Similarity	NPC474058
0.6821	Remote Similarity	NPC40488
0.6821	Remote Similarity	NPC101372
0.6818	Remote Similarity	NPC256288
0.6818	Remote Similarity	NPC159963
0.6807	Remote Similarity	NPC113946
0.6805	Remote Similarity	NPC70172
0.6805	Remote Similarity	NPC470508
0.6802	Remote Similarity	NPC285622
0.6802	Remote Similarity	NPC476425
0.6798	Remote Similarity	NPC291759
0.6796	Remote Similarity	NPC204970
0.6788	Remote Similarity	NPC207726
0.6788	Remote Similarity	NPC473297
0.6782	Remote Similarity	NPC186669
0.6782	Remote Similarity	NPC293472
0.6782	Remote Similarity	NPC151939
0.678	Remote Similarity	NPC2933
0.6779	Remote Similarity	NPC317758
0.6778	Remote Similarity	NPC469470
0.6778	Remote Similarity	NPC469501
0.6778	Remote Similarity	NPC174629
0.6766	Remote Similarity	NPC230869
0.6766	Remote Similarity	NPC193410
0.6765	Remote Similarity	NPC49954
0.6765	Remote Similarity	NPC474561
0.6761	Remote Similarity	NPC192270
0.6761	Remote Similarity	NPC476428
0.6746	Remote Similarity	NPC311276
0.6746	Remote Similarity	NPC476118
0.6742	Remote Similarity	NPC133591
0.6742	Remote Similarity	NPC62510
0.6742	Remote Similarity	NPC259626
0.674	Remote Similarity	NPC25401
0.6739	Remote Similarity	NPC90967
0.6733	Remote Similarity	NPC474926
0.6727	Remote Similarity	NPC478076
0.6726	Remote Similarity	NPC315368
0.6726	Remote Similarity	NPC248117
0.6725	Remote Similarity	NPC201700
0.6725	Remote Similarity	NPC154293
0.6724	Remote Similarity	NPC134586
0.672	Remote Similarity	NPC249040
0.6711	Remote Similarity	NPC328683
0.6711	Remote Similarity	NPC283130
0.6711	Remote Similarity	NPC295478
0.6708	Remote Similarity	NPC470824
0.6707	Remote Similarity	NPC61013
0.6705	Remote Similarity	NPC15840
0.6704	Remote Similarity	NPC473615
0.6704	Remote Similarity	NPC38823
0.6704	Remote Similarity	NPC207033
0.6687	Remote Similarity	NPC237649
0.6687	Remote Similarity	NPC300596
0.6686	Remote Similarity	NPC211997
0.6686	Remote Similarity	NPC280548
0.6685	Remote Similarity	NPC105055
0.6685	Remote Similarity	NPC22689
0.6667	Remote Similarity	NPC229484
0.6667	Remote Similarity	NPC54988
0.6667	Remote Similarity	NPC160105
0.6667	Remote Similarity	NPC472114
0.6667	Remote Similarity	NPC181928
0.6667	Remote Similarity	NPC67056
0.6667	Remote Similarity	NPC314394
0.6667	Remote Similarity	NPC302191
0.6667	Remote Similarity	NPC472115
0.6667	Remote Similarity	NPC14994
0.6649	Remote Similarity	NPC474077
0.6648	Remote Similarity	NPC473007
0.663	Remote Similarity	NPC292675
0.6629	Remote Similarity	NPC129624
0.6628	Remote Similarity	NPC167724
0.6628	Remote Similarity	NPC224970
0.6628	Remote Similarity	NPC223595
0.6627	Remote Similarity	NPC81229
0.6627	Remote Similarity	NPC255229
0.6623	Remote Similarity	NPC472414
0.6615	Remote Similarity	NPC477160
0.6613	Remote Similarity	NPC52557
0.6611	Remote Similarity	NPC476250
0.661	Remote Similarity	NPC300688
0.6609	Remote Similarity	NPC473880
0.6609	Remote Similarity	NPC314603
0.6607	Remote Similarity	NPC469762

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 NPC472103 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	128
0.1-0.2	414
0.2-0.3	627
0.3-0.4	1365
0.4-0.5	3256
0.5-0.6	2867
0.6-0.7	465
0.7-0.8	28
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
0.8039	Intermediate Similarity	NPD4121	Phase 3
0.8039	Intermediate Similarity	NPD4120	Approved
0.7987	Intermediate Similarity	NPD5742	Approved
0.7987	Intermediate Similarity	NPD5743	Approved
0.7987	Intermediate Similarity	NPD5741	Approved
0.7725	Intermediate Similarity	NPD7252	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2212	Approved
0.75	Intermediate Similarity	NPD2210	Approved
0.7468	Intermediate Similarity	NPD5595	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3329	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3864	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6506	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1108	Approved
0.7153	Intermediate Similarity	NPD1107	Approved
0.7133	Intermediate Similarity	NPD865	Approved
0.7133	Intermediate Similarity	NPD864	Approved
0.7133	Intermediate Similarity	NPD1922	Discontinued
0.7115	Intermediate Similarity	NPD6301	Phase 2
0.7114	Intermediate Similarity	NPD6359	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2622	Approved
0.7071	Intermediate Similarity	NPD3149	Approved
0.7071	Intermediate Similarity	NPD2659	Approved
0.7071	Intermediate Similarity	NPD3147	Approved
0.7071	Intermediate Similarity	NPD3148	Approved
0.7071	Intermediate Similarity	NPD2658	Approved
0.7071	Intermediate Similarity	NPD3150	Approved
0.7067	Intermediate Similarity	NPD3720	Discontinued
0.7067	Intermediate Similarity	NPD4274	Approved
0.7067	Intermediate Similarity	NPD4275	Approved
0.7047	Intermediate Similarity	NPD995	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5596	Phase 2
0.7	Intermediate Similarity	NPD5881	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1764	Approved
0.7	Intermediate Similarity	NPD1762	Approved
0.6975	Remote Similarity	NPD2188	Approved
0.6972	Remote Similarity	NPD4032	Approved
0.6972	Remote Similarity	NPD4031	Approved
0.6957	Remote Similarity	NPD6221	Approved
0.6957	Remote Similarity	NPD6222	Approved
0.6957	Remote Similarity	NPD1405	Approved
0.6939	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7522	Discontinued
0.6842	Remote Similarity	NPD2216	Approved
0.6842	Remote Similarity	NPD2215	Approved
0.6818	Remote Similarity	NPD5185	Approved
0.6818	Remote Similarity	NPD5184	Approved
0.6818	Remote Similarity	NPD5182	Approved
0.6788	Remote Similarity	NPD7969	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5631	Phase 3
0.6763	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.676	Remote Similarity	NPD4951	Discontinued
0.6746	Remote Similarity	NPD5138	Approved
0.6746	Remote Similarity	NPD5140	Approved
0.6739	Remote Similarity	NPD563	Approved
0.6739	Remote Similarity	NPD5717	Approved
0.6739	Remote Similarity	NPD564	Approved
0.6733	Remote Similarity	NPD1036	Approved
0.6724	Remote Similarity	NPD2381	Approved
0.6724	Remote Similarity	NPD2380	Approved
0.6724	Remote Similarity	NPD2382	Approved
0.6714	Remote Similarity	NPD2679	Approved
0.6714	Remote Similarity	NPD2678	Approved
0.6711	Remote Similarity	NPD478	Approved
0.6705	Remote Similarity	NPD6878	Phase 2
0.6705	Remote Similarity	NPD6879	Phase 2
0.6687	Remote Similarity	NPD4703	Approved
0.6687	Remote Similarity	NPD4702	Approved
0.6686	Remote Similarity	NPD1325	Approved
0.6686	Remote Similarity	NPD1326	Approved
0.6685	Remote Similarity	NPD2845	Phase 2
0.6685	Remote Similarity	NPD2843	Phase 2
0.6667	Remote Similarity	NPD7836	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2789	Approved
0.6645	Remote Similarity	NPD1595	Approved
0.6645	Remote Similarity	NPD1594	Phase 3
0.6644	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD4719	Phase 2
0.6642	Remote Similarity	NPD4119	Approved
0.6628	Remote Similarity	NPD2844	Phase 3
0.6627	Remote Similarity	NPD5599	Discontinued
0.6627	Remote Similarity	NPD3557	Approved
0.6627	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD3558	Approved
0.6627	Remote Similarity	NPD3556	Approved
0.6627	Remote Similarity	NPD3560	Approved
0.6626	Remote Similarity	NPD6378	Approved
0.6624	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD7342	Discontinued
0.661	Remote Similarity	NPD6595	Phase 3
0.6607	Remote Similarity	NPD6694	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4707	Clinical (unspecified phase)
0.659	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD1592	Phase 3
0.6578	Remote Similarity	NPD2176	Approved
0.6578	Remote Similarity	NPD2175	Phase 3
0.6578	Remote Similarity	NPD2177	Approved
0.6573	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6789	Approved
0.6561	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5989	Phase 1
0.6525	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5716	Approved
0.6522	Remote Similarity	NPD1908	Phase 2
0.6517	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6320	Approved
0.6513	Remote Similarity	NPD9587	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6885	Approved
0.6509	Remote Similarity	NPD6886	Approved
0.6509	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD7508	Discontinued
0.6503	Remote Similarity	NPD4499	Approved
0.6503	Remote Similarity	NPD5060	Phase 1
0.65	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD7200	Approved
0.6488	Remote Similarity	NPD5617	Suspended
0.6486	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD2383	Phase 1
0.6478	Remote Similarity	NPD4411	Phase 1
0.6478	Remote Similarity	NPD4410	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6283	Phase 2
0.6471	Remote Similarity	NPD6900	Discontinued
0.6467	Remote Similarity	NPD5077	Approved
0.6467	Remote Similarity	NPD5076	Approved
0.6464	Remote Similarity	NPD6557	Phase 2
0.6461	Remote Similarity	NPD8386	Phase 2
0.646	Remote Similarity	NPD3625	Discontinued
0.6458	Remote Similarity	NPD2038	Approved
0.6458	Remote Similarity	NPD2039	Approved
0.6457	Remote Similarity	NPD3824	Phase 1
0.6455	Remote Similarity	NPD4601	Approved
0.6455	Remote Similarity	NPD4600	Approved
0.645	Remote Similarity	NPD2468	Approved
0.645	Remote Similarity	NPD2469	Approved
0.645	Remote Similarity	NPD7105	Phase 1
0.6444	Remote Similarity	NPD7883	Discontinued
0.6442	Remote Similarity	NPD3717	Discontinued
0.6441	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD3983	Phase 3
0.6433	Remote Similarity	NPD7600	Phase 2
0.6424	Remote Similarity	NPD4218	Approved
0.6424	Remote Similarity	NPD4215	Approved
0.6424	Remote Similarity	NPD3131	Approved
0.6424	Remote Similarity	NPD4216	Approved
0.6424	Remote Similarity	NPD2612	Approved
0.6424	Remote Similarity	NPD2609	Approved
0.6424	Remote Similarity	NPD2608	Approved
0.6424	Remote Similarity	NPD2611	Approved
0.6424	Remote Similarity	NPD2610	Approved
0.6424	Remote Similarity	NPD4217	Approved
0.6424	Remote Similarity	NPD3132	Approved
0.6423	Remote Similarity	NPD4117	Approved
0.6416	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD4796	Discontinued
0.6414	Remote Similarity	NPD3066	Phase 2
0.6414	Remote Similarity	NPD4165	Phase 2
0.6413	Remote Similarity	NPD7628	Phase 3
0.6413	Remote Similarity	NPD7630	Phase 3
0.6413	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.641	Remote Similarity	NPD1068	Approved
0.6405	Remote Similarity	NPD2143	Discontinued
0.6404	Remote Similarity	NPD2144	Approved
0.6402	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD1742	Approved
0.6395	Remote Similarity	NPD19	Approved
0.6395	Remote Similarity	NPD1743	Approved
0.6389	Remote Similarity	NPD3038	Discontinued
0.6384	Remote Similarity	NPD5065	Approved
0.6376	Remote Similarity	NPD2218	Phase 2
0.6376	Remote Similarity	NPD2217	Approved
0.6375	Remote Similarity	NPD827	Approved
0.6374	Remote Similarity	NPD4514	Approved
0.6374	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7599	Phase 2
0.6374	Remote Similarity	NPD4860	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD4079	Approved
0.6369	Remote Similarity	NPD4076	Approved
0.6369	Remote Similarity	NPD6158	Phase 2
0.6369	Remote Similarity	NPD2322	Discovery
0.6358	Remote Similarity	NPD1953	Discontinued
0.6357	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD6026	Approved
0.6348	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4019	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD2613	Approved
0.6341	Remote Similarity	NPD2387	Approved
0.6333	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1710	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