NPASS Compound

Structure

NPC302844 OpenBabel07101718182D 31 32 0 0 1 0 0 0 0 0999 V2000 3.3799 3.7302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7398 4.2869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7149 -3.0958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9516 0.5152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4004 2.2318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5833 -1.2739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0969 2.3931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0777 2.5881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4258 -1.8614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5039 -0.6709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5289 -2.6481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7172 0.2261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9258 -2.7274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3937 -1.5700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3937 -2.5700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1297 0.3835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7755 1.4461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3383 -1.5700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3992 3.5351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0556 -2.3439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1998 -0.1442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3383 -2.5700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5277 -1.0700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5277 -3.0700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5267 0.3041 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3703 -0.4825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2053 1.2510 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5277 -4.0700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2671 -0.0402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1522 1.5725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 19 2 0 0 0 0 9 20 1 0 0 0 0 10 21 2 0 0 0 0 11 13 1 0 0 0 0 11 20 2 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 23 2 0 0 0 0 15 24 2 0 0 0 0 16 25 1 0 0 0 0 17 27 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 22 24 1 0 0 0 0 23 26 1 0 0 0 0 24 28 1 0 0 0 0 25 27 1 1 0 0 0 25 31 1 0 0 0 0 26 29 2 0 0 0 0 26 31 1 0 0 0 0 27 5 1 1 0 0 0 27 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.28
Volume:	475.141
LogP:	6.522
LogD:	4.978
LogS:	-4.309
# Rotatable Bonds:	4
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.43
Synthetic Accessibility Score:	5.109
Fsp3:	0.519
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.731
MDCK Permeability:	2.3335658625001088e-05
Pgp-inhibitor:	0.956
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.667
20% Bioavailability (F20%):	0.891
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	98.9830551147461%
Volume Distribution (VD):	0.789
Pgp-substrate:	1.3196574449539185%

ADMET: Metabolism

CYP1A2-inhibitor:	0.362
CYP1A2-substrate:	0.173
CYP2C19-inhibitor:	0.592
CYP2C19-substrate:	0.097
CYP2C9-inhibitor:	0.516
CYP2C9-substrate:	0.968
CYP2D6-inhibitor:	0.858
CYP2D6-substrate:	0.625
CYP3A4-inhibitor:	0.636
CYP3A4-substrate:	0.136

ADMET: Excretion

Clearance (CL):	6.412
Half-life (T1/2):	0.327

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.501
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.415
Skin Sensitization:	0.95
Carcinogencity:	0.029
Eye Corrosion:	0.004
Eye Irritation:	0.557
Respiratory Toxicity:	0.025

Download Data

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

Natural Product: NPC302844

Natural Product ID:	NPC302844
*Common Name:**	Callophycolide A
IUPAC Name:	(3E,7E,11S)-17-hydroxy-11-[(2R)-2-hydroxy-6-methylhept-5-en-2-yl]-4,8-dimethyl-12-oxabicyclo[12.3.1]octadeca-1(17),3,7,14(18),15-pentaen-13-one
Synonyms:
Standard InCHIKey:	XKADTDJBCKMTDO-ZWQBUCKISA-N
Standard InCHI:	InChI=1S/C27H38O4/c1-19(2)8-7-17-27(5,30)25-16-12-21(4)10-6-9-20(3)11-13-22-18-23(26(29)31-25)14-15-24(22)28/h8,10-11,14-15,18,25,28,30H,6-7,9,12-13,16-17H2,1-5H3/b20-11+,21-10+/t25-,27+/m0/s1
SMILES:	CC(=CCC[C@](C)([C@@H]1CC/C(=C/CC/C(=C/Cc2cc(ccc2O)C(=O)O1)/C)/C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1257966
PubChem CID:	49765073
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*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
NPO33001	macroalgae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20801038]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3
MIC	4

Activity Type	# Activity
Cell Line	2
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	7500.0	nM	PMID[458320]
NPT2155	Cell Line	SHP77	Homo sapiens	IC50	=	9200.0	nM	PMID[458320]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	5200.0	nM	PMID[458320]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	9100.0	nM	PMID[458320]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	9100.0	nM	PMID[458320]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	12000.0	nM	PMID[458320]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	250000.0	nM	PMID[458320]

☑ 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 NPC302844 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	270
0.1-0.2	1181
0.2-0.3	2965
0.3-0.4	7002
0.4-0.5	10930
0.5-0.6	4978
0.6-0.7	8630
0.7-0.8	6376
0.8-0.85	322
0.85-0.9	32
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9453	High Similarity	NPC473777
0.9398	High Similarity	NPC469911
0.936	High Similarity	NPC184219
0.9219	High Similarity	NPC473744
0.9213	High Similarity	NPC204579
0.92	High Similarity	NPC67300
0.9062	High Similarity	NPC110211
0.9044	High Similarity	NPC184053
0.8992	High Similarity	NPC121104
0.8837	High Similarity	NPC49938
0.8815	High Similarity	NPC475111
0.88	High Similarity	NPC273282
0.88	High Similarity	NPC474890
0.88	High Similarity	NPC94298
0.88	High Similarity	NPC161943
0.88	High Similarity	NPC27633
0.875	High Similarity	NPC475192
0.8731	High Similarity	NPC239855
0.8681	High Similarity	NPC11892
0.8681	High Similarity	NPC475093
0.8667	High Similarity	NPC204582
0.8652	High Similarity	NPC97188
0.8647	High Similarity	NPC327457
0.8647	High Similarity	NPC86774
0.864	High Similarity	NPC131192
0.864	High Similarity	NPC83718
0.8636	High Similarity	NPC2596
0.8611	High Similarity	NPC37642
0.8593	High Similarity	NPC114116
0.8592	High Similarity	NPC473023
0.8592	High Similarity	NPC469498
0.8571	High Similarity	NPC194979
0.8561	High Similarity	NPC64664
0.8538	High Similarity	NPC174991
0.8511	High Similarity	NPC469615
0.8507	High Similarity	NPC109778
0.8496	Intermediate Similarity	NPC2401
0.8485	Intermediate Similarity	NPC473751
0.8478	Intermediate Similarity	NPC170718
0.8473	Intermediate Similarity	NPC221798
0.8472	Intermediate Similarity	NPC17600
0.8456	Intermediate Similarity	NPC477281
0.8456	Intermediate Similarity	NPC477280
0.8456	Intermediate Similarity	NPC19719
0.8451	Intermediate Similarity	NPC213900
0.8451	Intermediate Similarity	NPC469683
0.844	Intermediate Similarity	NPC478250
0.8433	Intermediate Similarity	NPC226855
0.8429	Intermediate Similarity	NPC158472
0.8421	Intermediate Similarity	NPC37512
0.8417	Intermediate Similarity	NPC221104
0.8414	Intermediate Similarity	NPC52931
0.8406	Intermediate Similarity	NPC291454
0.8403	Intermediate Similarity	NPC14875
0.8392	Intermediate Similarity	NPC474044
0.8382	Intermediate Similarity	NPC327204
0.8382	Intermediate Similarity	NPC323379
0.838	Intermediate Similarity	NPC271451
0.8369	Intermediate Similarity	NPC470842
0.8367	Intermediate Similarity	NPC256141
0.8358	Intermediate Similarity	NPC217431
0.8357	Intermediate Similarity	NPC19622
0.8357	Intermediate Similarity	NPC473988
0.8357	Intermediate Similarity	NPC112789
0.8356	Intermediate Similarity	NPC180351
0.8346	Intermediate Similarity	NPC476022
0.8346	Intermediate Similarity	NPC474945
0.8346	Intermediate Similarity	NPC95309
0.8345	Intermediate Similarity	NPC471069
0.8345	Intermediate Similarity	NPC70380
0.8345	Intermediate Similarity	NPC194579
0.8345	Intermediate Similarity	NPC471068
0.8345	Intermediate Similarity	NPC71256
0.8333	Intermediate Similarity	NPC316769
0.8322	Intermediate Similarity	NPC113397
0.8322	Intermediate Similarity	NPC151607
0.8322	Intermediate Similarity	NPC42540
0.8321	Intermediate Similarity	NPC69403
0.8321	Intermediate Similarity	NPC291189
0.8309	Intermediate Similarity	NPC104854
0.8309	Intermediate Similarity	NPC15083
0.8298	Intermediate Similarity	NPC472600
0.8298	Intermediate Similarity	NPC275903
0.8298	Intermediate Similarity	NPC472601
0.8295	Intermediate Similarity	NPC473767
0.8295	Intermediate Similarity	NPC61779
0.8288	Intermediate Similarity	NPC472628
0.8288	Intermediate Similarity	NPC247219
0.8288	Intermediate Similarity	NPC327962
0.8286	Intermediate Similarity	NPC471072
0.8286	Intermediate Similarity	NPC33144
0.8286	Intermediate Similarity	NPC112135
0.8286	Intermediate Similarity	NPC471071
0.8286	Intermediate Similarity	NPC478200
0.8286	Intermediate Similarity	NPC94248
0.8286	Intermediate Similarity	NPC191835
0.8286	Intermediate Similarity	NPC212693
0.8286	Intermediate Similarity	NPC471070
0.8284	Intermediate Similarity	NPC158654
0.8281	Intermediate Similarity	NPC122117
0.8276	Intermediate Similarity	NPC66991
0.8276	Intermediate Similarity	NPC91902
0.8276	Intermediate Similarity	NPC81835
0.8273	Intermediate Similarity	NPC471345
0.8273	Intermediate Similarity	NPC156892
0.8271	Intermediate Similarity	NPC165556
0.8264	Intermediate Similarity	NPC258856
0.8264	Intermediate Similarity	NPC83272
0.8264	Intermediate Similarity	NPC75295
0.8261	Intermediate Similarity	NPC27643
0.8254	Intermediate Similarity	NPC242136
0.8252	Intermediate Similarity	NPC159721
0.8243	Intermediate Similarity	NPC477957
0.8239	Intermediate Similarity	NPC313123
0.8239	Intermediate Similarity	NPC472605
0.8239	Intermediate Similarity	NPC472603
0.8239	Intermediate Similarity	NPC478217
0.8239	Intermediate Similarity	NPC472604
0.8239	Intermediate Similarity	NPC307990
0.8239	Intermediate Similarity	NPC471587
0.8239	Intermediate Similarity	NPC472035
0.8239	Intermediate Similarity	NPC478201
0.8239	Intermediate Similarity	NPC16455
0.8235	Intermediate Similarity	NPC183348
0.8235	Intermediate Similarity	NPC123
0.8235	Intermediate Similarity	NPC163169
0.8235	Intermediate Similarity	NPC282230
0.8231	Intermediate Similarity	NPC472421
0.8222	Intermediate Similarity	NPC229894
0.8222	Intermediate Similarity	NPC193203
0.8219	Intermediate Similarity	NPC161955
0.8209	Intermediate Similarity	NPC475236
0.8207	Intermediate Similarity	NPC286038
0.8207	Intermediate Similarity	NPC229264
0.8201	Intermediate Similarity	NPC70680
0.8201	Intermediate Similarity	NPC476018
0.8201	Intermediate Similarity	NPC164136
0.8201	Intermediate Similarity	NPC18646
0.8201	Intermediate Similarity	NPC233350
0.8201	Intermediate Similarity	NPC182217
0.8201	Intermediate Similarity	NPC475029
0.8201	Intermediate Similarity	NPC142027
0.8201	Intermediate Similarity	NPC27407
0.82	Intermediate Similarity	NPC471787
0.8194	Intermediate Similarity	NPC277426
0.8194	Intermediate Similarity	NPC210425
0.8194	Intermediate Similarity	NPC86373
0.8194	Intermediate Similarity	NPC280404
0.8188	Intermediate Similarity	NPC66158
0.8182	Intermediate Similarity	NPC171870
0.8182	Intermediate Similarity	NPC82913
0.8182	Intermediate Similarity	NPC139171
0.8176	Intermediate Similarity	NPC471676
0.8176	Intermediate Similarity	NPC472420
0.8176	Intermediate Similarity	NPC471677
0.8176	Intermediate Similarity	NPC263384
0.8176	Intermediate Similarity	NPC472423
0.8176	Intermediate Similarity	NPC472422
0.8176	Intermediate Similarity	NPC474772
0.8176	Intermediate Similarity	NPC244577
0.8176	Intermediate Similarity	NPC472580
0.8176	Intermediate Similarity	NPC474744
0.8175	Intermediate Similarity	NPC470977
0.8175	Intermediate Similarity	NPC196979
0.8175	Intermediate Similarity	NPC470976
0.8169	Intermediate Similarity	NPC51181
0.8169	Intermediate Similarity	NPC470211
0.8169	Intermediate Similarity	NPC23257
0.8169	Intermediate Similarity	NPC327187
0.8163	Intermediate Similarity	NPC89442
0.8163	Intermediate Similarity	NPC104172
0.8163	Intermediate Similarity	NPC88886
0.8162	Intermediate Similarity	NPC66246
0.8162	Intermediate Similarity	NPC117899
0.8162	Intermediate Similarity	NPC170546
0.8156	Intermediate Similarity	NPC197666
0.8156	Intermediate Similarity	NPC126739
0.8156	Intermediate Similarity	NPC472602
0.8156	Intermediate Similarity	NPC317119
0.8154	Intermediate Similarity	NPC90522
0.8154	Intermediate Similarity	NPC328459
0.8151	Intermediate Similarity	NPC472627
0.8151	Intermediate Similarity	NPC477483
0.8151	Intermediate Similarity	NPC473133
0.8151	Intermediate Similarity	NPC325032
0.8151	Intermediate Similarity	NPC53362
0.8151	Intermediate Similarity	NPC222298
0.8151	Intermediate Similarity	NPC166583
0.8151	Intermediate Similarity	NPC47388
0.8151	Intermediate Similarity	NPC51070
0.8151	Intermediate Similarity	NPC470670
0.8143	Intermediate Similarity	NPC326847
0.8143	Intermediate Similarity	NPC64230
0.8143	Intermediate Similarity	NPC71638
0.8138	Intermediate Similarity	NPC197252
0.8138	Intermediate Similarity	NPC209040
0.8138	Intermediate Similarity	NPC236766
0.8138	Intermediate Similarity	NPC208293
0.8138	Intermediate Similarity	NPC469953
0.8133	Intermediate Similarity	NPC108937

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 NPC302844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	792
0.2-0.3	1584
0.3-0.4	2540
0.4-0.5	2052
0.5-0.6	1253
0.6-0.7	554
0.7-0.8	120
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.88	High Similarity	NPD9545	Approved
0.8429	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8369	Intermediate Similarity	NPD4628	Phase 3
0.8267	Intermediate Similarity	NPD7075	Discontinued
0.8188	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD230	Phase 1
0.8	Intermediate Similarity	NPD6801	Discontinued
0.7987	Intermediate Similarity	NPD4380	Phase 2
0.7971	Intermediate Similarity	NPD3764	Approved
0.7945	Intermediate Similarity	NPD6799	Approved
0.7923	Intermediate Similarity	NPD9493	Approved
0.792	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD2935	Discontinued
0.7815	Intermediate Similarity	NPD7411	Suspended
0.78	Intermediate Similarity	NPD7458	Discontinued
0.7748	Intermediate Similarity	NPD6599	Discontinued
0.7744	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1240	Approved
0.7727	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1549	Phase 2
0.7714	Intermediate Similarity	NPD6798	Discontinued
0.7712	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD7819	Suspended
0.7687	Intermediate Similarity	NPD6190	Approved
0.7676	Intermediate Similarity	NPD6355	Discontinued
0.7655	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2534	Approved
0.7651	Intermediate Similarity	NPD2532	Approved
0.7651	Intermediate Similarity	NPD2533	Approved
0.7651	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1510	Phase 2
0.7639	Intermediate Similarity	NPD2799	Discontinued
0.7622	Intermediate Similarity	NPD1607	Approved
0.7613	Intermediate Similarity	NPD7768	Phase 2
0.7603	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1934	Approved
0.7518	Intermediate Similarity	NPD9717	Approved
0.7517	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD3750	Approved
0.7483	Intermediate Similarity	NPD5049	Phase 3
0.7469	Intermediate Similarity	NPD5844	Phase 1
0.7469	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD2796	Approved
0.745	Intermediate Similarity	NPD2354	Approved
0.745	Intermediate Similarity	NPD3887	Approved
0.7447	Intermediate Similarity	NPD6832	Phase 2
0.7434	Intermediate Similarity	NPD5403	Approved
0.7391	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3882	Suspended
0.7383	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7003	Approved
0.7383	Intermediate Similarity	NPD8166	Discontinued
0.7379	Intermediate Similarity	NPD6651	Approved
0.7375	Intermediate Similarity	NPD6232	Discontinued
0.7368	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD1358	Approved
0.7361	Intermediate Similarity	NPD4060	Phase 1
0.7357	Intermediate Similarity	NPD1203	Approved
0.7357	Intermediate Similarity	NPD1164	Approved
0.7347	Intermediate Similarity	NPD1551	Phase 2
0.7346	Intermediate Similarity	NPD7473	Discontinued
0.7343	Intermediate Similarity	NPD2313	Discontinued
0.7338	Intermediate Similarity	NPD3455	Phase 2
0.7328	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD3817	Phase 2
0.7321	Intermediate Similarity	NPD8150	Discontinued
0.731	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5124	Phase 1
0.7308	Intermediate Similarity	NPD74	Approved
0.7308	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD9266	Approved
0.7305	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5401	Approved
0.7299	Intermediate Similarity	NPD4626	Approved
0.7297	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6002	Phase 3
0.7297	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6004	Phase 3
0.7297	Intermediate Similarity	NPD7266	Discontinued
0.7297	Intermediate Similarity	NPD6005	Phase 3
0.7292	Intermediate Similarity	NPD4062	Phase 3
0.7292	Intermediate Similarity	NPD6233	Phase 2
0.7279	Intermediate Similarity	NPD4308	Phase 3
0.7273	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1608	Approved
0.7266	Intermediate Similarity	NPD3972	Approved
0.7266	Intermediate Similarity	NPD9269	Phase 2
0.7261	Intermediate Similarity	NPD2801	Approved
0.7261	Intermediate Similarity	NPD8455	Phase 2
0.7256	Intermediate Similarity	NPD7286	Phase 2
0.7251	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD943	Approved
0.7235	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2797	Approved
0.7231	Intermediate Similarity	NPD9267	Approved
0.7231	Intermediate Similarity	NPD9263	Approved
0.7231	Intermediate Similarity	NPD9264	Approved
0.723	Intermediate Similarity	NPD5406	Approved
0.723	Intermediate Similarity	NPD5408	Approved
0.723	Intermediate Similarity	NPD5405	Approved
0.723	Intermediate Similarity	NPD5404	Approved
0.7229	Intermediate Similarity	NPD6559	Discontinued
0.7226	Intermediate Similarity	NPD3226	Approved
0.7226	Intermediate Similarity	NPD5691	Approved
0.7222	Intermediate Similarity	NPD3268	Approved
0.7212	Intermediate Similarity	NPD7074	Phase 3
0.7211	Intermediate Similarity	NPD7097	Phase 1
0.7208	Intermediate Similarity	NPD920	Approved
0.72	Intermediate Similarity	NPD1243	Approved
0.7195	Intermediate Similarity	NPD3818	Discontinued
0.7194	Intermediate Similarity	NPD422	Phase 1
0.7192	Intermediate Similarity	NPD447	Suspended
0.7181	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2353	Approved
0.7181	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2344	Approved
0.7178	Intermediate Similarity	NPD6166	Phase 2
0.7178	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2182	Approved
0.7174	Intermediate Similarity	NPD1778	Approved
0.7171	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD5953	Discontinued
0.7169	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD1241	Discontinued
0.7162	Intermediate Similarity	NPD3748	Approved
0.716	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD3134	Approved
0.7152	Intermediate Similarity	NPD7054	Approved
0.7134	Intermediate Similarity	NPD6386	Approved
0.7134	Intermediate Similarity	NPD6385	Approved
0.7134	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2424	Discontinued
0.7126	Intermediate Similarity	NPD7685	Pre-registration
0.7125	Intermediate Similarity	NPD3749	Approved
0.7124	Intermediate Similarity	NPD1511	Approved
0.7115	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4476	Approved
0.7114	Intermediate Similarity	NPD4477	Approved
0.7111	Intermediate Similarity	NPD2629	Approved
0.7108	Intermediate Similarity	NPD7472	Approved
0.7107	Intermediate Similarity	NPD5402	Approved
0.7101	Intermediate Similarity	NPD9268	Approved
0.7097	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7843	Approved
0.7086	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2800	Approved
0.7081	Intermediate Similarity	NPD919	Approved
0.7078	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2346	Discontinued
0.7063	Intermediate Similarity	NPD2798	Approved
0.7063	Intermediate Similarity	NPD5647	Approved
0.7063	Intermediate Similarity	NPD1019	Discontinued
0.7059	Intermediate Similarity	NPD7440	Discontinued
0.7055	Intermediate Similarity	NPD6663	Approved
0.705	Intermediate Similarity	NPD17	Approved
0.7047	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD2684	Approved
0.7044	Intermediate Similarity	NPD1465	Phase 2
0.7042	Intermediate Similarity	NPD3225	Approved
0.7042	Intermediate Similarity	NPD8651	Approved
0.7042	Intermediate Similarity	NPD1283	Approved
0.7041	Intermediate Similarity	NPD8312	Approved
0.7041	Intermediate Similarity	NPD8313	Approved
0.7037	Intermediate Similarity	NPD5494	Approved
0.7034	Intermediate Similarity	NPD7095	Approved
0.7032	Intermediate Similarity	NPD1512	Approved
0.7032	Intermediate Similarity	NPD6273	Approved
0.7029	Intermediate Similarity	NPD1894	Discontinued
0.7024	Intermediate Similarity	NPD7251	Discontinued
0.7021	Intermediate Similarity	NPD1481	Phase 2
0.7018	Intermediate Similarity	NPD8434	Phase 2
0.7014	Intermediate Similarity	NPD5736	Approved
0.7007	Intermediate Similarity	NPD4307	Phase 2
0.7	Intermediate Similarity	NPD2438	Suspended
0.7	Intermediate Similarity	NPD3847	Discontinued
0.7	Intermediate Similarity	NPD3496	Discontinued
0.6994	Remote Similarity	NPD6959	Discontinued
0.6993	Remote Similarity	NPD1470	Approved
0.6993	Remote Similarity	NPD2309	Approved
0.6992	Remote Similarity	NPD2067	Discontinued
0.6988	Remote Similarity	NPD7177	Discontinued
0.6988	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD411	Approved
0.6985	Remote Similarity	NPD9281	Approved
0.6982	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7808	Phase 3
0.698	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1652	Phase 2

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