NPASS Compound

Structure

NPC133591 OpenBabel07101718182D 39 43 0 0 1 0 0 0 0 0999 V2000 6.7350 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4158 -2.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 -2.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1590 -2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0651 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0029 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0029 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1991 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2709 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.1991 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.3331 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4670 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4670 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 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 3.2709 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 11.9311 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0651 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3331 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6010 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3331 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6010 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 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 15 2 0 0 0 0 6 16 2 0 0 0 0 7 8 1 0 0 0 0 7 26 1 0 0 0 0 8 28 1 0 0 0 0 9 18 1 0 0 0 0 10 29 1 0 0 0 0 11 14 2 0 0 0 0 11 37 1 0 0 0 0 12 2 1 6 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 9 1 6 0 0 0 13 14 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 10 1 1 0 0 0 17 19 1 0 0 0 0 17 38 1 0 0 0 0 18 28 1 0 0 0 0 18 30 1 1 0 0 0 19 20 1 0 0 0 0 19 31 1 6 0 0 0 20 21 1 0 0 0 0 20 32 1 1 0 0 0 21 24 1 0 0 0 0 21 33 1 6 0 0 0 22 28 1 0 0 0 0 22 34 2 0 0 0 0 23 37 1 0 0 0 0 23 39 1 1 0 0 0 24 38 1 0 0 0 0 24 39 1 1 0 0 0 25 26 1 0 0 0 0 25 27 2 0 0 0 0 25 35 1 0 0 0 0 26 36 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	548.2
Volume:	515.701
LogP:	-0.13
LogD:	-0.111
LogS:	-2.107
# Rotatable Bonds:	7
TPSA:	198.48
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.191
Synthetic Accessibility Score:	5.223
Fsp3:	0.538
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.194
MDCK Permeability:	3.966746589867398e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.867
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.246
Plasma Protein Binding (PPB):	34.20317840576172%
Volume Distribution (VD):	0.354
Pgp-substrate:	51.437591552734375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.455
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.145

ADMET: Excretion

Clearance (CL):	0.946
Half-life (T1/2):	0.432

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.27
Drug-inuced Liver Injury (DILI):	0.659
AMES Toxicity:	0.208
Rat Oral Acute Toxicity:	0.185
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.102
Carcinogencity:	0.892
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.874

Download Data

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

Natural Product: NPC133591

Natural Product ID:	NPC133591
*Common Name:**	Paratunamide D
IUPAC Name:	(3S,4R,4aS,6R)-4-ethenyl-6-hydroxy-7-[2-[(3S)-3-hydroxy-2-oxo-1H-indol-3-yl]ethyl]-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyridin-8-one
Synonyms:	Paratunamide D
Standard InCHIKey:	QPIBCHJEPFSMPX-NXTSHNLASA-N
Standard InCHI:	InChI=1S/C26H32N2O11/c1-2-12-13-9-18(30)28(8-7-26(36)15-5-3-4-6-16(15)27-25(26)35)22(34)14(13)11-37-23(12)39-24-21(33)20(32)19(31)17(10-29)38-24/h2-6,11-13,17-21,23-24,29-33,36H,1,7-10H2,(H,27,35)/t12-,13+,17-,18-,19-,20+,21-,23+,24+,26+/m1/s1
SMILES:	C=C[C@H]1[C@@H](OC=C2[C@H]1C[C@@H](O)N(C2=O)CC[C@@]1(O)C(=Nc2c1cccc2)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457837
PubChem CID:	16091682
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO18036	Cinnamodendron axillare	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067176]
NPO18036	Cinnamodendron axillare	Species	Canellaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	6.0	ug.mL-1	PMID[450074]

☑ 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 NPC133591 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	242
0.1-0.2	1068
0.2-0.3	2971
0.3-0.4	10526
0.4-0.5	18052
0.5-0.6	8725
0.6-0.7	1045
0.7-0.8	58
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9939	High Similarity	NPC291759
0.9819	High Similarity	NPC38823
0.9819	High Similarity	NPC207033
0.7874	Intermediate Similarity	NPC320064
0.776	Intermediate Similarity	NPC475962
0.7624	Intermediate Similarity	NPC298851
0.7624	Intermediate Similarity	NPC181138
0.7624	Intermediate Similarity	NPC210415
0.7624	Intermediate Similarity	NPC21752
0.7624	Intermediate Similarity	NPC276993
0.7624	Intermediate Similarity	NPC293255
0.75	Intermediate Similarity	NPC311357
0.7446	Intermediate Similarity	NPC129624
0.736	Intermediate Similarity	NPC211525
0.736	Intermediate Similarity	NPC153694
0.733	Intermediate Similarity	NPC174788
0.7308	Intermediate Similarity	NPC278887
0.7253	Intermediate Similarity	NPC52059
0.7253	Intermediate Similarity	NPC470069
0.7236	Intermediate Similarity	NPC474077
0.7233	Intermediate Similarity	NPC476114
0.7222	Intermediate Similarity	NPC63210
0.7222	Intermediate Similarity	NPC263709
0.7222	Intermediate Similarity	NPC97380
0.7222	Intermediate Similarity	NPC243673
0.7222	Intermediate Similarity	NPC148468
0.7222	Intermediate Similarity	NPC310403
0.7174	Intermediate Similarity	NPC469462
0.7165	Intermediate Similarity	NPC28510
0.7143	Intermediate Similarity	NPC472100
0.7143	Intermediate Similarity	NPC472121
0.7087	Intermediate Similarity	NPC111732
0.7085	Intermediate Similarity	NPC267414
0.7081	Intermediate Similarity	NPC82070
0.7056	Intermediate Similarity	NPC161827
0.7049	Intermediate Similarity	NPC253667
0.7049	Intermediate Similarity	NPC35510
0.7035	Intermediate Similarity	NPC317672
0.7031	Intermediate Similarity	NPC245741
0.703	Intermediate Similarity	NPC476115
0.7026	Intermediate Similarity	NPC471196
0.7026	Intermediate Similarity	NPC471195
0.7024	Intermediate Similarity	NPC477548
0.7	Intermediate Similarity	NPC50997
0.7	Intermediate Similarity	NPC160127
0.6985	Remote Similarity	NPC329024
0.6985	Remote Similarity	NPC475559
0.6967	Remote Similarity	NPC52254
0.6959	Remote Similarity	NPC282092
0.695	Remote Similarity	NPC59033
0.6931	Remote Similarity	NPC32451
0.693	Remote Similarity	NPC26928
0.6927	Remote Similarity	NPC474905
0.6923	Remote Similarity	NPC477157
0.6923	Remote Similarity	NPC477156
0.6919	Remote Similarity	NPC203972
0.6916	Remote Similarity	NPC475271
0.6912	Remote Similarity	NPC25442
0.6912	Remote Similarity	NPC12944
0.6898	Remote Similarity	NPC248903
0.6891	Remote Similarity	NPC327373
0.6891	Remote Similarity	NPC322043
0.6887	Remote Similarity	NPC108826
0.6866	Remote Similarity	NPC320748
0.6866	Remote Similarity	NPC324245
0.6848	Remote Similarity	NPC476194
0.6848	Remote Similarity	NPC471203
0.6847	Remote Similarity	NPC328559
0.6845	Remote Similarity	NPC156044
0.6837	Remote Similarity	NPC325775
0.6822	Remote Similarity	NPC99724
0.6821	Remote Similarity	NPC469460
0.6816	Remote Similarity	NPC302548
0.6805	Remote Similarity	NPC197680
0.6805	Remote Similarity	NPC259098
0.6804	Remote Similarity	NPC325093
0.6802	Remote Similarity	NPC316405
0.6798	Remote Similarity	NPC79223
0.6791	Remote Similarity	NPC148124
0.6791	Remote Similarity	NPC472106
0.6768	Remote Similarity	NPC174629
0.6762	Remote Similarity	NPC292517
0.6757	Remote Similarity	NPC57453
0.6754	Remote Similarity	NPC473354
0.6751	Remote Similarity	NPC328798
0.6742	Remote Similarity	NPC472103
0.6736	Remote Similarity	NPC274002
0.6736	Remote Similarity	NPC472331
0.6736	Remote Similarity	NPC126515
0.6735	Remote Similarity	NPC318020
0.6722	Remote Similarity	NPC254798
0.672	Remote Similarity	NPC470971
0.6719	Remote Similarity	NPC50016
0.6718	Remote Similarity	NPC477159
0.6717	Remote Similarity	NPC182814
0.6716	Remote Similarity	NPC20593
0.6715	Remote Similarity	NPC309498
0.6714	Remote Similarity	NPC162812
0.6702	Remote Similarity	NPC273755
0.6702	Remote Similarity	NPC307640
0.6701	Remote Similarity	NPC39822
0.67	Remote Similarity	NPC204970
0.6699	Remote Similarity	NPC168250
0.6685	Remote Similarity	NPC308197
0.6685	Remote Similarity	NPC242000
0.6684	Remote Similarity	NPC471053
0.6684	Remote Similarity	NPC85651
0.6684	Remote Similarity	NPC472101
0.6684	Remote Similarity	NPC471051
0.6684	Remote Similarity	NPC471048
0.6684	Remote Similarity	NPC472120
0.6684	Remote Similarity	NPC469915
0.6684	Remote Similarity	NPC471050
0.6684	Remote Similarity	NPC471052
0.6684	Remote Similarity	NPC472117
0.6684	Remote Similarity	NPC471049
0.6684	Remote Similarity	NPC294951
0.6683	Remote Similarity	NPC472329
0.6683	Remote Similarity	NPC472330
0.6681	Remote Similarity	NPC472435
0.6667	Remote Similarity	NPC30570
0.6667	Remote Similarity	NPC184161
0.6667	Remote Similarity	NPC472436
0.6667	Remote Similarity	NPC472114
0.6667	Remote Similarity	NPC472115
0.6651	Remote Similarity	NPC326027
0.665	Remote Similarity	NPC472191
0.665	Remote Similarity	NPC127647
0.6649	Remote Similarity	NPC10730
0.6649	Remote Similarity	NPC313757
0.6649	Remote Similarity	NPC10875
0.6649	Remote Similarity	NPC45037
0.6649	Remote Similarity	NPC49353
0.6648	Remote Similarity	NPC49565
0.6636	Remote Similarity	NPC106593
0.6631	Remote Similarity	NPC474058
0.6631	Remote Similarity	NPC477158
0.6623	Remote Similarity	NPC472434
0.662	Remote Similarity	NPC140311
0.6616	Remote Similarity	NPC262725
0.6612	Remote Similarity	NPC4108
0.6606	Remote Similarity	NPC473667
0.66	Remote Similarity	NPC105055
0.66	Remote Similarity	NPC22689
0.6597	Remote Similarity	NPC40234
0.6597	Remote Similarity	NPC257354
0.6595	Remote Similarity	NPC473297
0.6587	Remote Similarity	NPC14339
0.6583	Remote Similarity	NPC473815
0.6582	Remote Similarity	NPC476321
0.658	Remote Similarity	NPC473402
0.658	Remote Similarity	NPC471165
0.658	Remote Similarity	NPC13367
0.658	Remote Similarity	NPC476227
0.658	Remote Similarity	NPC279871
0.658	Remote Similarity	NPC477462
0.6579	Remote Similarity	NPC294516
0.6579	Remote Similarity	NPC19555
0.6579	Remote Similarity	NPC107938
0.6578	Remote Similarity	NPC291359
0.6566	Remote Similarity	NPC472209
0.6564	Remote Similarity	NPC269750
0.6564	Remote Similarity	NPC194671
0.6564	Remote Similarity	NPC475094
0.6564	Remote Similarity	NPC99891
0.6562	Remote Similarity	NPC170751
0.6562	Remote Similarity	NPC230611
0.6557	Remote Similarity	NPC326333
0.6548	Remote Similarity	NPC471526
0.654	Remote Similarity	NPC477160
0.6538	Remote Similarity	NPC246983
0.6538	Remote Similarity	NPC475448
0.6526	Remote Similarity	NPC244856
0.6522	Remote Similarity	NPC473341
0.652	Remote Similarity	NPC108804
0.652	Remote Similarity	NPC476218
0.6519	Remote Similarity	NPC237240
0.6519	Remote Similarity	NPC31171
0.6517	Remote Similarity	NPC163961
0.6517	Remote Similarity	NPC473305
0.651	Remote Similarity	NPC475204
0.651	Remote Similarity	NPC475123
0.6508	Remote Similarity	NPC191863
0.6508	Remote Similarity	NPC476231
0.6508	Remote Similarity	NPC133470
0.6508	Remote Similarity	NPC289776
0.6507	Remote Similarity	NPC268077
0.6498	Remote Similarity	NPC37957
0.6495	Remote Similarity	NPC155506
0.6495	Remote Similarity	NPC159767
0.6495	Remote Similarity	NPC26108
0.6494	Remote Similarity	NPC319995
0.6494	Remote Similarity	NPC17567
0.6494	Remote Similarity	NPC289415
0.649	Remote Similarity	NPC475223
0.6489	Remote Similarity	NPC471122
0.6488	Remote Similarity	NPC144314
0.6484	Remote Similarity	NPC71539
0.6484	Remote Similarity	NPC250960
0.6481	Remote Similarity	NPC473800

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 NPC133591 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	456
0.2-0.3	666
0.3-0.4	1570
0.4-0.5	3412
0.5-0.6	2691
0.6-0.7	200
0.7-0.8	0
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
0.6961	Remote Similarity	NPD8417	Discontinued
0.6865	Remote Similarity	NPD2995	Approved
0.6778	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD4951	Discontinued
0.6746	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3067	Approved
0.6636	Remote Similarity	NPD8325	Phase 3
0.6636	Remote Similarity	NPD8326	Phase 3
0.6636	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3824	Phase 1
0.6535	Remote Similarity	NPD7570	Approved
0.6535	Remote Similarity	NPD7569	Approved
0.6524	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7584	Approved
0.652	Remote Similarity	NPD5582	Discontinued
0.6519	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4430	Phase 2
0.6477	Remote Similarity	NPD2791	Discontinued
0.6455	Remote Similarity	NPD7600	Phase 2
0.6445	Remote Similarity	NPD7583	Approved
0.6444	Remote Similarity	NPD4168	Approved
0.6436	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD7811	Phase 3
0.6425	Remote Similarity	NPD6874	Approved
0.6425	Remote Similarity	NPD7810	Phase 3
0.6415	Remote Similarity	NPD7585	Approved
0.6402	Remote Similarity	NPD7599	Phase 2
0.6389	Remote Similarity	NPD4897	Phase 2
0.6386	Remote Similarity	NPD8025	Phase 2
0.6383	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6395	Phase 2
0.6374	Remote Similarity	NPD2575	Approved
0.6364	Remote Similarity	NPD6879	Phase 2
0.6364	Remote Similarity	NPD6878	Phase 2
0.6344	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD8323	Discontinued
0.6333	Remote Similarity	NPD3068	Approved
0.6333	Remote Similarity	NPD3605	Approved
0.633	Remote Similarity	NPD5742	Approved
0.633	Remote Similarity	NPD5743	Approved
0.633	Remote Similarity	NPD5741	Approved
0.6324	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD5042	Phase 1
0.6321	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD6557	Phase 2
0.6313	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7256	Discontinued
0.6308	Remote Similarity	NPD2216	Approved
0.6308	Remote Similarity	NPD2215	Approved
0.6305	Remote Similarity	NPD4334	Discontinued
0.6303	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD7777	Approved
0.6298	Remote Similarity	NPD3069	Approved
0.6298	Remote Similarity	NPD7778	Approved
0.6298	Remote Similarity	NPD53	Approved
0.6295	Remote Similarity	NPD8059	Phase 3
0.6295	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7613	Discontinued
0.6284	Remote Similarity	NPD6676	Phase 2
0.6283	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD4121	Phase 3
0.6277	Remote Similarity	NPD4120	Approved
0.627	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD2578	Phase 3
0.6263	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7011	Discontinued
0.6256	Remote Similarity	NPD7795	Phase 2
0.625	Remote Similarity	NPD6206	Phase 1
0.625	Remote Similarity	NPD4871	Phase 2
0.625	Remote Similarity	NPD7186	Phase 3
0.6244	Remote Similarity	NPD5076	Approved
0.6244	Remote Similarity	NPD6058	Phase 2
0.6244	Remote Similarity	NPD5077	Approved
0.6239	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD4501	Approved
0.6238	Remote Similarity	NPD4500	Approved
0.6237	Remote Similarity	NPD5823	Approved
0.6237	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD5120	Approved
0.6236	Remote Similarity	NPD5119	Approved
0.6236	Remote Similarity	NPD5121	Approved
0.623	Remote Similarity	NPD4485	Approved
0.6224	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6261	Phase 3
0.6218	Remote Similarity	NPD8370	Discontinued
0.6216	Remote Similarity	NPD5506	Approved
0.6216	Remote Similarity	NPD5507	Approved
0.6216	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD8146	Phase 2
0.6209	Remote Similarity	NPD7476	Discontinued
0.6198	Remote Similarity	NPD6063	Approved
0.6198	Remote Similarity	NPD2996	Approved
0.6195	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD7628	Phase 3
0.6195	Remote Similarity	NPD7630	Phase 3
0.6195	Remote Similarity	NPD2845	Phase 2
0.6195	Remote Similarity	NPD2843	Phase 2
0.6193	Remote Similarity	NPD5997	Discontinued
0.619	Remote Similarity	NPD6248	Phase 2
0.619	Remote Similarity	NPD6249	Phase 2
0.6184	Remote Similarity	NPD7796	Approved
0.6184	Remote Similarity	NPD7797	Approved
0.6181	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD6641	Approved
0.6181	Remote Similarity	NPD6642	Approved
0.6181	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD6885	Approved
0.6178	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD6886	Approved
0.6176	Remote Similarity	NPD2210	Approved
0.6176	Remote Similarity	NPD2212	Approved
0.6171	Remote Similarity	NPD3437	Discontinued
0.617	Remote Similarity	NPD8468	Phase 2
0.6162	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD2904	Discontinued
0.615	Remote Similarity	NPD4086	Phase 1
0.615	Remote Similarity	NPD4682	Phase 2
0.6145	Remote Similarity	NPD6309	Approved
0.6145	Remote Similarity	NPD6311	Approved
0.6145	Remote Similarity	NPD6310	Approved
0.6143	Remote Similarity	NPD5856	Discontinued
0.6141	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.614	Remote Similarity	NPD7263	Phase 2
0.6139	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD4315	Phase 2
0.6135	Remote Similarity	NPD4941	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7890	Discontinued
0.6121	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD7396	Approved
0.612	Remote Similarity	NPD4152	Approved
0.6117	Remote Similarity	NPD3321	Discontinued
0.6114	Remote Similarity	NPD2160	Approved
0.6114	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD2159	Approved
0.6114	Remote Similarity	NPD2627	Approved
0.6114	Remote Similarity	NPD2625	Approved
0.6114	Remote Similarity	NPD2628	Approved
0.6114	Remote Similarity	NPD2626	Approved
0.6108	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD5150	Phase 2
0.6103	Remote Similarity	NPD7035	Approved
0.6103	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD7036	Phase 3
0.6102	Remote Similarity	NPD4620	Approved
0.6102	Remote Similarity	NPD4617	Approved
0.6102	Remote Similarity	NPD5201	Approved
0.6102	Remote Similarity	NPD2613	Approved
0.6102	Remote Similarity	NPD5203	Approved
0.61	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD7560	Approved
0.6091	Remote Similarity	NPD5186	Approved
0.6091	Remote Similarity	NPD5183	Approved
0.6089	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD7086	Phase 2
0.6089	Remote Similarity	NPD3912	Discontinued
0.6089	Remote Similarity	NPD7820	Phase 3
0.6087	Remote Similarity	NPD6681	Discovery
0.6087	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD3277	Phase 3
0.608	Remote Similarity	NPD7247	Discontinued
0.6078	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD3802	Phase 3
0.6075	Remote Similarity	NPD6669	Phase 2
0.6075	Remote Similarity	NPD7205	Discontinued
0.6075	Remote Similarity	NPD5487	Phase 1
0.6074	Remote Similarity	NPD8461	Discontinued
0.6071	Remote Similarity	NPD7805	Phase 3
0.6067	Remote Similarity	NPD4274	Approved
0.6067	Remote Similarity	NPD4275	Approved
0.6067	Remote Similarity	NPD3720	Discontinued
0.6065	Remote Similarity	NPD7043	Discontinued
0.6062	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD2388	Discontinued
0.6059	Remote Similarity	NPD5596	Phase 2
0.6058	Remote Similarity	NPD5214	Phase 2
0.6057	Remote Similarity	NPD5578	Approved
0.6057	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD3125	Approved
0.6056	Remote Similarity	NPD5185	Approved
0.6056	Remote Similarity	NPD5182	Approved
0.6056	Remote Similarity	NPD5184	Approved
0.6055	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD3153	Approved
0.6049	Remote Similarity	NPD5444	Phase 1
0.6049	Remote Similarity	NPD3154	Approved
0.6048	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD7891	Discontinued
0.6042	Remote Similarity	NPD1663	Discontinued

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