NPASS Compound

Structure

NPC472123 OpenBabel07101719522D 22 26 0 0 1 0 0 0 0 0999 V2000 -2.3242 3.7877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8035 2.9576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5721 1.2549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5721 0.2962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7419 1.7342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7419 -0.1831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2161 1.1146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3899 2.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9789 2.0911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1091 4.0545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3242 2.1274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9117 1.2549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4654 1.8102 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.5511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0769 2.4388 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9117 0.2962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3433 2.5270 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5168 0.8757 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5635 0.7755 0.0000 C 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 -1.9067 1.7515 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -4.0668 4.0115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 11 2 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 12 2 0 0 0 0 6 16 2 0 0 0 0 7 18 1 0 0 0 0 8 14 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 21 1 0 0 0 0 10 15 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 13 7 1 6 0 0 0 13 15 1 0 0 0 0 14 19 2 0 0 0 0 15 17 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 1 0 0 0 18 19 1 0 0 0 0 18 21 1 1 0 0 0 19 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.17
Volume:	311.999
LogP:	2.758
LogD:	2.797
LogS:	-2.672
# Rotatable Bonds:	1
TPSA:	39.26
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.794
Synthetic Accessibility Score:	5.134
Fsp3:	0.474
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:	-4.923
MDCK Permeability:	2.0951249098288827e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.641
Human Intestinal Absorption (HIA):	0.431
20% Bioavailability (F20%):	0.643
30% Bioavailability (F30%):	0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.932
Plasma Protein Binding (PPB):	79.58026885986328%
Volume Distribution (VD):	1.631
Pgp-substrate:	17.158864974975586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.468
CYP1A2-substrate:	0.23
CYP2C19-inhibitor:	0.156
CYP2C19-substrate:	0.211
CYP2C9-inhibitor:	0.108
CYP2C9-substrate:	0.776
CYP2D6-inhibitor:	0.242
CYP2D6-substrate:	0.857
CYP3A4-inhibitor:	0.607
CYP3A4-substrate:	0.77

ADMET: Excretion

Clearance (CL):	10.372
Half-life (T1/2):	0.208

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.166
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.071
Rat Oral Acute Toxicity:	0.976
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.264
Carcinogencity:	0.948
Eye Corrosion:	0.012
Eye Irritation:	0.038
Respiratory Toxicity:	0.992

Download Data

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

Natural Product: NPC472123

Natural Product ID:	NPC472123
*Common Name:**	VXTDUGOBAOLMED-JTZQFXNDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VXTDUGOBAOLMED-JTZQFXNDSA-N
Standard InCHI:	InChI=1S/C19H22N2O/c1-2-11-9-21-17-8-14-12-5-3-4-6-16(12)20-19(14)18(21)7-13(11)15(17)10-22/h2-6,13,15,17-18,20,22H,7-10H2,1H3/b11-2-/t13-,15?,17+,18+/m1/s1
SMILES:	C/C=C1/CN2[C@@H]3C([C@@H]1C[C@H]2c1c(C3)c2c([nH]1)cccc2)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338256
PubChem CID:	5281962
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003759] Macroline 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
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[448439]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[448439]

☑ 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 NPC472123 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	368
0.1-0.2	2004
0.2-0.3	13658
0.3-0.4	18696
0.4-0.5	3487
0.5-0.6	2274
0.6-0.7	1505
0.7-0.8	625
0.8-0.85	57
0.85-0.9	13
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9448	High Similarity	NPC139291
0.9448	High Similarity	NPC472108
0.943	High Similarity	NPC317430
0.9226	High Similarity	NPC469470
0.9226	High Similarity	NPC469501
0.9096	High Similarity	NPC472110
0.9096	High Similarity	NPC472109
0.8963	High Similarity	NPC329688
0.8963	High Similarity	NPC189812
0.8909	High Similarity	NPC24594
0.8909	High Similarity	NPC472122
0.8862	High Similarity	NPC472105
0.8862	High Similarity	NPC187827
0.8857	High Similarity	NPC52557
0.8802	High Similarity	NPC133261
0.8758	High Similarity	NPC255229
0.8758	High Similarity	NPC81229
0.8757	High Similarity	NPC19679
0.8757	High Similarity	NPC249040
0.8743	High Similarity	NPC326575
0.8721	High Similarity	NPC175474
0.8596	High Similarity	NPC472294
0.8571	High Similarity	NPC285469
0.8563	High Similarity	NPC472112
0.8529	High Similarity	NPC15840
0.8466	Intermediate Similarity	NPC472113
0.8457	Intermediate Similarity	NPC95783
0.8452	Intermediate Similarity	NPC88097
0.8444	Intermediate Similarity	NPC313985
0.8444	Intermediate Similarity	NPC249150
0.8444	Intermediate Similarity	NPC79129
0.8444	Intermediate Similarity	NPC81654
0.8444	Intermediate Similarity	NPC195461
0.8444	Intermediate Similarity	NPC49196
0.8436	Intermediate Similarity	NPC50503
0.8424	Intermediate Similarity	NPC87755
0.8364	Intermediate Similarity	NPC16667
0.8354	Intermediate Similarity	NPC474880
0.8354	Intermediate Similarity	NPC221786
0.8333	Intermediate Similarity	NPC475422
0.8324	Intermediate Similarity	NPC472104
0.8323	Intermediate Similarity	NPC474561
0.8323	Intermediate Similarity	NPC49954
0.8303	Intermediate Similarity	NPC229173
0.8295	Intermediate Similarity	NPC63199
0.8295	Intermediate Similarity	NPC196251
0.8295	Intermediate Similarity	NPC102338
0.8295	Intermediate Similarity	NPC111602
0.8282	Intermediate Similarity	NPC207726
0.8263	Intermediate Similarity	NPC470508
0.8239	Intermediate Similarity	NPC472323
0.8232	Intermediate Similarity	NPC469785
0.8214	Intermediate Similarity	NPC54988
0.8214	Intermediate Similarity	NPC160105
0.8204	Intermediate Similarity	NPC271797
0.8204	Intermediate Similarity	NPC21174
0.8199	Intermediate Similarity	NPC21605
0.8194	Intermediate Similarity	NPC198988
0.8182	Intermediate Similarity	NPC469762
0.8166	Intermediate Similarity	NPC201700
0.8166	Intermediate Similarity	NPC63751
0.8161	Intermediate Similarity	NPC233936
0.815	Intermediate Similarity	NPC219336
0.8144	Intermediate Similarity	NPC282231
0.8141	Intermediate Similarity	NPC325252
0.8133	Intermediate Similarity	NPC67056
0.8133	Intermediate Similarity	NPC230869
0.8133	Intermediate Similarity	NPC475990
0.8129	Intermediate Similarity	NPC314603
0.8125	Intermediate Similarity	NPC79062
0.8125	Intermediate Similarity	NPC472107
0.8122	Intermediate Similarity	NPC245916
0.8118	Intermediate Similarity	NPC280548
0.8113	Intermediate Similarity	NPC63157
0.8113	Intermediate Similarity	NPC473868
0.811	Intermediate Similarity	NPC73952
0.811	Intermediate Similarity	NPC25008
0.811	Intermediate Similarity	NPC259644
0.811	Intermediate Similarity	NPC469765
0.811	Intermediate Similarity	NPC469760
0.811	Intermediate Similarity	NPC469786
0.811	Intermediate Similarity	NPC469763
0.8092	Intermediate Similarity	NPC183662
0.8092	Intermediate Similarity	NPC217372
0.8092	Intermediate Similarity	NPC15573
0.8084	Intermediate Similarity	NPC279918
0.8079	Intermediate Similarity	NPC478077
0.8075	Intermediate Similarity	NPC470440
0.8068	Intermediate Similarity	NPC258480
0.8061	Intermediate Similarity	NPC211572
0.8061	Intermediate Similarity	NPC70922
0.8061	Intermediate Similarity	NPC470507
0.8061	Intermediate Similarity	NPC80597
0.8061	Intermediate Similarity	NPC75540
0.8061	Intermediate Similarity	NPC212376
0.8059	Intermediate Similarity	NPC154293
0.805	Intermediate Similarity	NPC59084
0.8043	Intermediate Similarity	NPC254240
0.8043	Intermediate Similarity	NPC312870
0.8043	Intermediate Similarity	NPC294909
0.8043	Intermediate Similarity	NPC128265
0.8043	Intermediate Similarity	NPC199851
0.8035	Intermediate Similarity	NPC121903
0.8023	Intermediate Similarity	NPC34508
0.8012	Intermediate Similarity	NPC474897
0.8011	Intermediate Similarity	NPC143533
0.8	Intermediate Similarity	NPC243716
0.8	Intermediate Similarity	NPC469896
0.7989	Intermediate Similarity	NPC151939
0.7988	Intermediate Similarity	NPC194640
0.7988	Intermediate Similarity	NPC311276
0.7978	Intermediate Similarity	NPC66210
0.7977	Intermediate Similarity	NPC275305
0.7977	Intermediate Similarity	NPC472586
0.7977	Intermediate Similarity	NPC37423
0.7966	Intermediate Similarity	NPC472119
0.7955	Intermediate Similarity	NPC113626
0.7955	Intermediate Similarity	NPC314394
0.7947	Intermediate Similarity	NPC126066
0.7943	Intermediate Similarity	NPC472443
0.7937	Intermediate Similarity	NPC475910
0.7937	Intermediate Similarity	NPC2949
0.7931	Intermediate Similarity	NPC203754
0.7931	Intermediate Similarity	NPC150048
0.7927	Intermediate Similarity	NPC37548
0.791	Intermediate Similarity	NPC48938
0.791	Intermediate Similarity	NPC163055
0.7904	Intermediate Similarity	NPC141353
0.7901	Intermediate Similarity	NPC472097
0.7898	Intermediate Similarity	NPC300688
0.7886	Intermediate Similarity	NPC68354
0.7886	Intermediate Similarity	NPC59269
0.7882	Intermediate Similarity	NPC40779
0.7879	Intermediate Similarity	NPC33421
0.7877	Intermediate Similarity	NPC474707
0.7869	Intermediate Similarity	NPC19692
0.7869	Intermediate Similarity	NPC220151
0.7861	Intermediate Similarity	NPC158129
0.7857	Intermediate Similarity	NPC129721
0.7853	Intermediate Similarity	NPC314372
0.7845	Intermediate Similarity	NPC314333
0.7845	Intermediate Similarity	NPC329858
0.7841	Intermediate Similarity	NPC215795
0.7841	Intermediate Similarity	NPC270009
0.7841	Intermediate Similarity	NPC176199
0.784	Intermediate Similarity	NPC20144
0.7838	Intermediate Similarity	NPC473640
0.7835	Intermediate Similarity	NPC183407
0.7833	Intermediate Similarity	NPC204565
0.7833	Intermediate Similarity	NPC317030
0.7829	Intermediate Similarity	NPC280852
0.7824	Intermediate Similarity	NPC471080
0.7824	Intermediate Similarity	NPC469592
0.7821	Intermediate Similarity	NPC15102
0.7816	Intermediate Similarity	NPC97525
0.7816	Intermediate Similarity	NPC161861
0.7809	Intermediate Similarity	NPC472444
0.7803	Intermediate Similarity	NPC194411
0.7801	Intermediate Similarity	NPC476116
0.7799	Intermediate Similarity	NPC218268
0.7797	Intermediate Similarity	NPC91179
0.779	Intermediate Similarity	NPC173028
0.779	Intermediate Similarity	NPC213629
0.779	Intermediate Similarity	NPC65215
0.7784	Intermediate Similarity	NPC248454
0.7778	Intermediate Similarity	NPC476118
0.7778	Intermediate Similarity	NPC469541
0.7778	Intermediate Similarity	NPC102423
0.7772	Intermediate Similarity	NPC57994
0.7772	Intermediate Similarity	NPC289299
0.7753	Intermediate Similarity	NPC192270
0.7744	Intermediate Similarity	NPC204141
0.7742	Intermediate Similarity	NPC265576
0.7738	Intermediate Similarity	NPC38736
0.7737	Intermediate Similarity	NPC472111
0.773	Intermediate Similarity	NPC190296
0.7725	Intermediate Similarity	NPC470233
0.7719	Intermediate Similarity	NPC194881
0.7716	Intermediate Similarity	NPC52254
0.7716	Intermediate Similarity	NPC115611
0.7714	Intermediate Similarity	NPC313791
0.7713	Intermediate Similarity	NPC475506
0.7711	Intermediate Similarity	NPC187951
0.7711	Intermediate Similarity	NPC470126
0.7707	Intermediate Similarity	NPC22079
0.7704	Intermediate Similarity	NPC476041
0.7704	Intermediate Similarity	NPC304926
0.7701	Intermediate Similarity	NPC100321
0.7696	Intermediate Similarity	NPC166492
0.7696	Intermediate Similarity	NPC473362
0.7688	Intermediate Similarity	NPC109447
0.7688	Intermediate Similarity	NPC232130
0.7684	Intermediate Similarity	NPC234987
0.7684	Intermediate Similarity	NPC293472
0.7683	Intermediate Similarity	NPC242556
0.768	Intermediate Similarity	NPC94752
0.7674	Intermediate Similarity	NPC78375
0.7674	Intermediate Similarity	NPC469813
0.7674	Intermediate Similarity	NPC476446
0.7673	Intermediate Similarity	NPC253580

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 NPC472123 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	513
0.2-0.3	844
0.3-0.4	1576
0.4-0.5	2664
0.5-0.6	2300
0.6-0.7	880
0.7-0.8	155
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8444	Intermediate Similarity	NPD4600	Approved
0.8444	Intermediate Similarity	NPD4601	Approved
0.8373	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD1326	Approved
0.8118	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD1325	Approved
0.8043	Intermediate Similarity	NPD4501	Approved
0.8043	Intermediate Similarity	NPD4500	Approved
0.8035	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6595	Phase 3
0.7977	Intermediate Similarity	NPD5065	Approved
0.795	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD4076	Approved
0.7943	Intermediate Similarity	NPD4079	Approved
0.7898	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD3506	Approved
0.7886	Intermediate Similarity	NPD3505	Approved
0.7845	Intermediate Similarity	NPD4499	Approved
0.7831	Intermediate Similarity	NPD2882	Phase 1
0.7829	Intermediate Similarity	NPD2382	Approved
0.7829	Intermediate Similarity	NPD2381	Approved
0.7829	Intermediate Similarity	NPD2380	Approved
0.779	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5138	Approved
0.7778	Intermediate Similarity	NPD5140	Approved
0.7772	Intermediate Similarity	NPD4602	Approved
0.7771	Intermediate Similarity	NPD4462	Approved
0.7771	Intermediate Similarity	NPD4463	Approved
0.774	Intermediate Similarity	NPD8386	Phase 2
0.7735	Intermediate Similarity	NPD8431	Approved
0.7725	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6158	Phase 2
0.7716	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1683	Approved
0.7684	Intermediate Similarity	NPD4181	Approved
0.7684	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD2144	Approved
0.7679	Intermediate Similarity	NPD2837	Discontinued
0.7669	Intermediate Similarity	NPD1722	Approved
0.7657	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3038	Discontinued
0.7637	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD5596	Phase 2
0.7609	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD5913	Phase 3
0.7592	Intermediate Similarity	NPD8272	Phase 2
0.7576	Intermediate Similarity	NPD5254	Discontinued
0.7572	Intermediate Similarity	NPD3323	Discontinued
0.7571	Intermediate Similarity	NPD6492	Phase 2
0.7571	Intermediate Similarity	NPD482	Approved
0.7562	Intermediate Similarity	NPD3385	Approved
0.7561	Intermediate Similarity	NPD1592	Phase 3
0.7546	Intermediate Similarity	NPD786	Approved
0.7545	Intermediate Similarity	NPD4703	Approved
0.7545	Intermediate Similarity	NPD4702	Approved
0.7543	Intermediate Similarity	NPD4639	Approved
0.7543	Intermediate Similarity	NPD4640	Approved
0.7543	Intermediate Similarity	NPD4638	Approved
0.7543	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD5021	Discontinued
0.7528	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD6227	Discontinued
0.7514	Intermediate Similarity	NPD2092	Phase 2
0.7514	Intermediate Similarity	NPD2095	Phase 2
0.7514	Intermediate Similarity	NPD2094	Phase 2
0.7513	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD2091	Phase 2
0.7473	Intermediate Similarity	NPD2096	Phase 2
0.7472	Intermediate Similarity	NPD4128	Approved
0.7461	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD7957	Phase 1
0.746	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD2383	Phase 1
0.7423	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD750	Phase 2
0.7409	Intermediate Similarity	NPD8114	Approved
0.7409	Intermediate Similarity	NPD8115	Approved
0.7403	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD3100	Discontinued
0.7385	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD8408	Discontinued
0.7362	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD8072	Approved
0.7353	Intermediate Similarity	NPD7271	Approved
0.7351	Intermediate Similarity	NPD3961	Discontinued
0.7345	Intermediate Similarity	NPD5862	Discovery
0.7345	Intermediate Similarity	NPD2844	Phase 3
0.7341	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8322	Phase 2
0.7333	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5104	Approved
0.733	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6285	Phase 2
0.732	Intermediate Similarity	NPD5426	Phase 3
0.7316	Intermediate Similarity	NPD5003	Discontinued
0.7312	Intermediate Similarity	NPD3654	Approved
0.7312	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5473	Discontinued
0.7306	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7944	Discontinued
0.7296	Intermediate Similarity	NPD5658	Approved
0.7294	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD3404	Approved
0.7283	Intermediate Similarity	NPD6178	Phase 3
0.7282	Intermediate Similarity	NPD7731	Approved
0.7282	Intermediate Similarity	NPD7730	Approved
0.7278	Intermediate Similarity	NPD7469	Discontinued
0.7268	Intermediate Similarity	NPD4203	Approved
0.7268	Intermediate Similarity	NPD7867	Phase 1
0.7268	Intermediate Similarity	NPD4204	Approved
0.7267	Intermediate Similarity	NPD4121	Phase 3
0.7267	Intermediate Similarity	NPD4120	Approved
0.7263	Intermediate Similarity	NPD3610	Approved
0.7263	Intermediate Similarity	NPD7935	Phase 2
0.7263	Intermediate Similarity	NPD3609	Approved
0.7263	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD4520	Approved
0.7258	Intermediate Similarity	NPD8020	Approved
0.7258	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD8021	Approved
0.7247	Intermediate Similarity	NPD2641	Approved
0.7247	Intermediate Similarity	NPD2640	Approved
0.7247	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6301	Phase 2
0.7243	Intermediate Similarity	NPD5555	Phase 1
0.7241	Intermediate Similarity	NPD4326	Phase 2
0.724	Intermediate Similarity	NPD6249	Phase 2
0.724	Intermediate Similarity	NPD6248	Phase 2
0.7238	Intermediate Similarity	NPD4075	Phase 2
0.7235	Intermediate Similarity	NPD4547	Phase 3
0.7232	Intermediate Similarity	NPD2915	Discontinued
0.7228	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5742	Approved
0.7225	Intermediate Similarity	NPD7948	Phase 1
0.7225	Intermediate Similarity	NPD5741	Approved
0.7225	Intermediate Similarity	NPD5743	Approved
0.7216	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD3394	Approved
0.7214	Intermediate Similarity	NPD3389	Approved
0.7214	Intermediate Similarity	NPD3393	Approved
0.7212	Intermediate Similarity	NPD7824	Approved
0.7211	Intermediate Similarity	NPD7618	Phase 3
0.7211	Intermediate Similarity	NPD7619	Phase 3
0.7202	Intermediate Similarity	NPD3717	Discontinued
0.72	Intermediate Similarity	NPD5255	Approved
0.7194	Intermediate Similarity	NPD3003	Approved
0.7192	Intermediate Similarity	NPD7194	Discontinued
0.7188	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6281	Approved
0.7179	Intermediate Similarity	NPD4886	Phase 2
0.7178	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6828	Phase 2
0.7167	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3864	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2172	Phase 1
0.715	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD3330	Phase 1
0.7143	Intermediate Similarity	NPD5100	Phase 3
0.7143	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD8073	Approved
0.712	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD7953	Approved
0.7109	Intermediate Similarity	NPD7951	Approved
0.7109	Intermediate Similarity	NPD7790	Approved
0.7109	Intermediate Similarity	NPD7952	Approved
0.7109	Intermediate Similarity	NPD7791	Approved
0.7109	Intermediate Similarity	NPD7950	Approved
0.7109	Intermediate Similarity	NPD7789	Approved
0.7108	Intermediate Similarity	NPD6554	Approved
0.7108	Intermediate Similarity	NPD45	Approved
0.7108	Intermediate Similarity	NPD1262	Discovery
0.7107	Intermediate Similarity	NPD6403	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4615	Phase 2
0.7101	Intermediate Similarity	NPD4047	Discontinued
0.71	Intermediate Similarity	NPD7470	Discontinued
0.7098	Intermediate Similarity	NPD4397	Phase 1
0.7088	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2150	Discontinued
0.7085	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD7817	Phase 1
0.7074	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD3002	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD3116	Approved
0.7072	Intermediate Similarity	NPD3117	Approved
0.7071	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD1038	Approved
0.7068	Intermediate Similarity	NPD802	Phase 2
0.7062	Intermediate Similarity	NPD2175	Phase 3

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