NPASS Compound

Structure

NPC291759 OpenBabel07101718232D 40 44 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 2.4049 -5.0000 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 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 2.4049 -4.0000 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 3 2 0 0 0 0 2 37 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 16 2 0 0 0 0 7 17 2 0 0 0 0 8 9 1 0 0 0 0 8 27 1 0 0 0 0 9 29 1 0 0 0 0 10 19 1 0 0 0 0 11 30 1 0 0 0 0 12 15 2 0 0 0 0 12 38 1 0 0 0 0 13 3 1 6 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 10 1 6 0 0 0 14 15 1 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 11 1 1 0 0 0 18 20 1 0 0 0 0 18 39 1 0 0 0 0 19 29 1 0 0 0 0 19 37 1 1 0 0 0 20 21 1 0 0 0 0 20 31 1 6 0 0 0 21 22 1 0 0 0 0 21 32 1 1 0 0 0 22 25 1 0 0 0 0 22 33 1 6 0 0 0 23 29 1 0 0 0 0 23 34 2 0 0 0 0 24 38 1 0 0 0 0 24 40 1 1 0 0 0 25 39 1 0 0 0 0 25 40 1 1 0 0 0 26 27 1 0 0 0 0 26 28 2 0 0 0 0 26 35 1 0 0 0 0 27 36 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	562.22
Volume:	532.997
LogP:	0.165
LogD:	0.676
LogS:	-2.358
# Rotatable Bonds:	8
TPSA:	187.48
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.211
Synthetic Accessibility Score:	5.238
Fsp3:	0.556
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:	-6.043
MDCK Permeability:	4.72107385576237e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.888
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.241
Plasma Protein Binding (PPB):	36.956817626953125%
Volume Distribution (VD):	0.416
Pgp-substrate:	53.44807052612305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.591
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	0.939
Half-life (T1/2):	0.384

ADMET: Toxicity

hERG Blockers:	0.094
Human Hepatotoxicity (H-HT):	0.39
Drug-inuced Liver Injury (DILI):	0.788
AMES Toxicity:	0.436
Rat Oral Acute Toxicity:	0.182
Maximum Recommended Daily Dose:	0.88
Skin Sensitization:	0.099
Carcinogencity:	0.91
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.697

Download Data

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

Natural Product: NPC291759

Natural Product ID:	NPC291759
*Common Name:**	Paratunamide A
IUPAC Name:	(3S,4R,4aS,6R)-4-ethenyl-7-[2-[(3S)-3-hydroxy-2-oxo-1H-indol-3-yl]ethyl]-6-methoxy-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:
Standard InCHIKey:	XEQPPTNZKGNKKE-OVINQPFISA-N
Standard InCHI:	InChI=1S/C27H34N2O11/c1-3-13-14-10-19(37-2)29(9-8-27(36)16-6-4-5-7-17(16)28-26(27)35)23(34)15(14)12-38-24(13)40-25-22(33)21(32)20(31)18(11-30)39-25/h3-7,12-14,18-22,24-25,30-33,36H,1,8-11H2,2H3,(H,28,35)/t13-,14+,18-,19-,20-,21+,22-,24+,25+,27+/m1/s1
SMILES:	CO[C@@H]1C[C@H]2[C@@H](C=C)[C@@H](OC=C2C(=O)N1CC[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:	CHEMBL504945
PubChem CID:	16091680
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	>	10.0	ug.mL-1	PMID[487381]

☑ 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 NPC291759 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	224
0.1-0.2	1033
0.2-0.3	2745
0.3-0.4	10286
0.4-0.5	18035
0.5-0.6	9130
0.6-0.7	1171
0.7-0.8	62
0.8-0.85	5
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	NPC133591
0.976	High Similarity	NPC207033
0.976	High Similarity	NPC38823
0.7931	Intermediate Similarity	NPC320064
0.7814	Intermediate Similarity	NPC475962
0.768	Intermediate Similarity	NPC210415
0.768	Intermediate Similarity	NPC298851
0.768	Intermediate Similarity	NPC181138
0.768	Intermediate Similarity	NPC21752
0.768	Intermediate Similarity	NPC276993
0.768	Intermediate Similarity	NPC293255
0.7551	Intermediate Similarity	NPC311357
0.75	Intermediate Similarity	NPC129624
0.7416	Intermediate Similarity	NPC153694
0.7416	Intermediate Similarity	NPC211525
0.7363	Intermediate Similarity	NPC278887
0.7308	Intermediate Similarity	NPC470069
0.7308	Intermediate Similarity	NPC52059
0.7295	Intermediate Similarity	NPC174788
0.7286	Intermediate Similarity	NPC474077
0.7278	Intermediate Similarity	NPC310403
0.7278	Intermediate Similarity	NPC97380
0.7278	Intermediate Similarity	NPC148468
0.7278	Intermediate Similarity	NPC63210
0.7278	Intermediate Similarity	NPC263709
0.7278	Intermediate Similarity	NPC243673
0.7228	Intermediate Similarity	NPC469462
0.7216	Intermediate Similarity	NPC28510
0.72	Intermediate Similarity	NPC472100
0.7198	Intermediate Similarity	NPC472121
0.7198	Intermediate Similarity	NPC476114
0.7136	Intermediate Similarity	NPC267414
0.7129	Intermediate Similarity	NPC82070
0.7111	Intermediate Similarity	NPC161827
0.7104	Intermediate Similarity	NPC35510
0.7104	Intermediate Similarity	NPC253667
0.7083	Intermediate Similarity	NPC245741
0.7077	Intermediate Similarity	NPC471196
0.7077	Intermediate Similarity	NPC471195
0.7073	Intermediate Similarity	NPC477548
0.7053	Intermediate Similarity	NPC111732
0.7035	Intermediate Similarity	NPC329024
0.7035	Intermediate Similarity	NPC475559
0.7014	Intermediate Similarity	NPC52254
0.701	Intermediate Similarity	NPC282092
0.7	Intermediate Similarity	NPC317672
0.6995	Remote Similarity	NPC476115
0.698	Remote Similarity	NPC32451
0.6978	Remote Similarity	NPC477156
0.6978	Remote Similarity	NPC477157
0.6976	Remote Similarity	NPC474905
0.697	Remote Similarity	NPC203972
0.6965	Remote Similarity	NPC160127
0.6965	Remote Similarity	NPC50997
0.6963	Remote Similarity	NPC475271
0.6961	Remote Similarity	NPC12944
0.6961	Remote Similarity	NPC25442
0.6944	Remote Similarity	NPC248903
0.6934	Remote Similarity	NPC108826
0.6915	Remote Similarity	NPC59033
0.6915	Remote Similarity	NPC320748
0.6915	Remote Similarity	NPC324245
0.6902	Remote Similarity	NPC476194
0.6902	Remote Similarity	NPC471203
0.6898	Remote Similarity	NPC26928
0.6897	Remote Similarity	NPC328559
0.6893	Remote Similarity	NPC156044
0.6888	Remote Similarity	NPC325775
0.6872	Remote Similarity	NPC469460
0.6866	Remote Similarity	NPC302548
0.6856	Remote Similarity	NPC322043
0.6856	Remote Similarity	NPC327373
0.6853	Remote Similarity	NPC316405
0.6847	Remote Similarity	NPC79223
0.6845	Remote Similarity	NPC472106
0.6837	Remote Similarity	NPC148124
0.6818	Remote Similarity	NPC174629
0.681	Remote Similarity	NPC292517
0.6806	Remote Similarity	NPC473354
0.6802	Remote Similarity	NPC57453
0.6802	Remote Similarity	NPC328798
0.6798	Remote Similarity	NPC472103
0.6791	Remote Similarity	NPC99724
0.6788	Remote Similarity	NPC126515
0.6788	Remote Similarity	NPC472331
0.6788	Remote Similarity	NPC274002
0.6778	Remote Similarity	NPC254798
0.6772	Remote Similarity	NPC470971
0.6771	Remote Similarity	NPC50016
0.6769	Remote Similarity	NPC325093
0.6769	Remote Similarity	NPC477159
0.6768	Remote Similarity	NPC182814
0.6765	Remote Similarity	NPC259098
0.6765	Remote Similarity	NPC197680
0.6761	Remote Similarity	NPC162812
0.6754	Remote Similarity	NPC307640
0.6754	Remote Similarity	NPC273755
0.6753	Remote Similarity	NPC39822
0.675	Remote Similarity	NPC204970
0.6746	Remote Similarity	NPC168250
0.6742	Remote Similarity	NPC308197
0.674	Remote Similarity	NPC242000
0.6738	Remote Similarity	NPC471052
0.6738	Remote Similarity	NPC472120
0.6738	Remote Similarity	NPC472117
0.6738	Remote Similarity	NPC471051
0.6738	Remote Similarity	NPC472101
0.6738	Remote Similarity	NPC471053
0.6737	Remote Similarity	NPC469915
0.6735	Remote Similarity	NPC471048
0.6735	Remote Similarity	NPC294951
0.6735	Remote Similarity	NPC471049
0.6735	Remote Similarity	NPC471050
0.6732	Remote Similarity	NPC472329
0.6732	Remote Similarity	NPC472330
0.6724	Remote Similarity	NPC472435
0.6721	Remote Similarity	NPC184161
0.672	Remote Similarity	NPC472114
0.672	Remote Similarity	NPC472115
0.6714	Remote Similarity	NPC30570
0.6709	Remote Similarity	NPC472436
0.6704	Remote Similarity	NPC49565
0.6703	Remote Similarity	NPC10875
0.6703	Remote Similarity	NPC10730
0.6702	Remote Similarity	NPC313757
0.6701	Remote Similarity	NPC45037
0.6701	Remote Similarity	NPC318020
0.6701	Remote Similarity	NPC49353
0.67	Remote Similarity	NPC127647
0.67	Remote Similarity	NPC472191
0.6698	Remote Similarity	NPC326027
0.6684	Remote Similarity	NPC474058
0.6684	Remote Similarity	NPC477158
0.6683	Remote Similarity	NPC20593
0.6683	Remote Similarity	NPC309498
0.6682	Remote Similarity	NPC106593
0.6667	Remote Similarity	NPC4108
0.6667	Remote Similarity	NPC262725
0.6667	Remote Similarity	NPC140311
0.6651	Remote Similarity	NPC473667
0.6649	Remote Similarity	NPC40234
0.6649	Remote Similarity	NPC85651
0.6649	Remote Similarity	NPC257354
0.6649	Remote Similarity	NPC473297
0.6635	Remote Similarity	NPC14339
0.6633	Remote Similarity	NPC473815
0.6633	Remote Similarity	NPC476321
0.6632	Remote Similarity	NPC279871
0.6632	Remote Similarity	NPC473402
0.6632	Remote Similarity	NPC13367
0.6632	Remote Similarity	NPC476227
0.6632	Remote Similarity	NPC294516
0.6632	Remote Similarity	NPC471165
0.6632	Remote Similarity	NPC19555
0.6632	Remote Similarity	NPC477462
0.6632	Remote Similarity	NPC107938
0.6631	Remote Similarity	NPC291359
0.6616	Remote Similarity	NPC472209
0.6615	Remote Similarity	NPC269750
0.6615	Remote Similarity	NPC194671
0.6615	Remote Similarity	NPC230611
0.6607	Remote Similarity	NPC170751
0.6604	Remote Similarity	NPC326333
0.6599	Remote Similarity	NPC471526
0.6594	Remote Similarity	NPC472434
0.6588	Remote Similarity	NPC477160
0.6587	Remote Similarity	NPC246983
0.6587	Remote Similarity	NPC475448
0.6576	Remote Similarity	NPC473341
0.6575	Remote Similarity	NPC237240
0.6575	Remote Similarity	NPC31171
0.6573	Remote Similarity	NPC244856
0.6569	Remote Similarity	NPC108804
0.6569	Remote Similarity	NPC476218
0.6567	Remote Similarity	NPC163961
0.6567	Remote Similarity	NPC22689
0.6567	Remote Similarity	NPC105055
0.6567	Remote Similarity	NPC473305
0.6562	Remote Similarity	NPC475123
0.6562	Remote Similarity	NPC475204
0.6561	Remote Similarity	NPC133470
0.6561	Remote Similarity	NPC476231
0.6561	Remote Similarity	NPC289776
0.6561	Remote Similarity	NPC191863
0.6555	Remote Similarity	NPC268077
0.6546	Remote Similarity	NPC155506
0.6546	Remote Similarity	NPC159767
0.6546	Remote Similarity	NPC26108
0.6544	Remote Similarity	NPC37957
0.6543	Remote Similarity	NPC471122
0.6538	Remote Similarity	NPC475223
0.6537	Remote Similarity	NPC144314
0.6535	Remote Similarity	NPC99891
0.6531	Remote Similarity	NPC475094
0.653	Remote Similarity	NPC71539
0.653	Remote Similarity	NPC250960
0.6526	Remote Similarity	NPC292143
0.6526	Remote Similarity	NPC139506
0.6526	Remote Similarity	NPC189116
0.6524	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 NPC291759 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	451
0.2-0.3	659
0.3-0.4	1513
0.4-0.5	3350
0.5-0.6	2798
0.6-0.7	232
0.7-0.8	1
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
0.7017	Intermediate Similarity	NPD8417	Discontinued
0.6919	Remote Similarity	NPD2995	Approved
0.6833	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4951	Discontinued
0.6794	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.676	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3067	Approved
0.6683	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD8326	Phase 3
0.6682	Remote Similarity	NPD8325	Phase 3
0.6682	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD7570	Approved
0.6584	Remote Similarity	NPD7569	Approved
0.6578	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7584	Approved
0.6569	Remote Similarity	NPD5582	Discontinued
0.6556	Remote Similarity	NPD4430	Phase 2
0.6534	Remote Similarity	NPD2791	Discontinued
0.6528	Remote Similarity	NPD3824	Phase 1
0.6508	Remote Similarity	NPD7600	Phase 2
0.65	Remote Similarity	NPD4168	Approved
0.6493	Remote Similarity	NPD7583	Approved
0.6489	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD7810	Phase 3
0.6473	Remote Similarity	NPD7811	Phase 3
0.6473	Remote Similarity	NPD6874	Approved
0.6462	Remote Similarity	NPD7585	Approved
0.6455	Remote Similarity	NPD7599	Phase 2
0.6436	Remote Similarity	NPD6395	Phase 2
0.6436	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD8025	Phase 2
0.6435	Remote Similarity	NPD4897	Phase 2
0.6429	Remote Similarity	NPD2575	Approved
0.6414	Remote Similarity	NPD6879	Phase 2
0.6414	Remote Similarity	NPD6878	Phase 2
0.6393	Remote Similarity	NPD8323	Discontinued
0.6389	Remote Similarity	NPD3605	Approved
0.6389	Remote Similarity	NPD3068	Approved
0.6383	Remote Similarity	NPD5741	Approved
0.6383	Remote Similarity	NPD5743	Approved
0.6383	Remote Similarity	NPD5742	Approved
0.6373	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5042	Phase 1
0.6364	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7256	Discontinued
0.6359	Remote Similarity	NPD2216	Approved
0.6359	Remote Similarity	NPD2215	Approved
0.6355	Remote Similarity	NPD4334	Discontinued
0.6351	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7778	Approved
0.6346	Remote Similarity	NPD53	Approved
0.6346	Remote Similarity	NPD7777	Approved
0.6344	Remote Similarity	NPD7613	Discontinued
0.6339	Remote Similarity	NPD8059	Phase 3
0.6339	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4121	Phase 3
0.633	Remote Similarity	NPD4120	Approved
0.6327	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD2578	Phase 3
0.6316	Remote Similarity	NPD7011	Discontinued
0.6313	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD7795	Phase 2
0.6302	Remote Similarity	NPD4871	Phase 2
0.6298	Remote Similarity	NPD6206	Phase 1
0.6293	Remote Similarity	NPD6058	Phase 2
0.6293	Remote Similarity	NPD5077	Approved
0.6293	Remote Similarity	NPD5076	Approved
0.6292	Remote Similarity	NPD5121	Approved
0.6292	Remote Similarity	NPD5119	Approved
0.6292	Remote Similarity	NPD5120	Approved
0.6291	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD6557	Phase 2
0.6286	Remote Similarity	NPD4500	Approved
0.6286	Remote Similarity	NPD4501	Approved
0.6283	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD4485	Approved
0.627	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD6261	Phase 3
0.6264	Remote Similarity	NPD3069	Approved
0.6262	Remote Similarity	NPD8146	Phase 2
0.6261	Remote Similarity	NPD8370	Discontinued
0.6261	Remote Similarity	NPD5506	Approved
0.6261	Remote Similarity	NPD5507	Approved
0.6256	Remote Similarity	NPD7476	Discontinued
0.625	Remote Similarity	NPD6063	Approved
0.625	Remote Similarity	NPD6676	Phase 2
0.625	Remote Similarity	NPD2996	Approved
0.6244	Remote Similarity	NPD5997	Discontinued
0.6244	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7628	Phase 3
0.6244	Remote Similarity	NPD7630	Phase 3
0.6238	Remote Similarity	NPD6248	Phase 2
0.6238	Remote Similarity	NPD6249	Phase 2
0.6235	Remote Similarity	NPD2212	Approved
0.6235	Remote Similarity	NPD2210	Approved
0.6231	Remote Similarity	NPD6642	Approved
0.6231	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD6641	Approved
0.623	Remote Similarity	NPD6886	Approved
0.623	Remote Similarity	NPD6885	Approved
0.6228	Remote Similarity	NPD7796	Approved
0.6228	Remote Similarity	NPD7797	Approved
0.6222	Remote Similarity	NPD7186	Phase 3
0.6216	Remote Similarity	NPD3437	Discontinued
0.6213	Remote Similarity	NPD8468	Phase 2
0.6212	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD5823	Approved
0.6205	Remote Similarity	NPD2904	Discontinued
0.6203	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD4682	Phase 2
0.6196	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4086	Phase 1
0.6193	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7263	Phase 2
0.6184	Remote Similarity	NPD4941	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD4315	Phase 2
0.6181	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD4152	Approved
0.6171	Remote Similarity	NPD2628	Approved
0.6171	Remote Similarity	NPD2625	Approved
0.6171	Remote Similarity	NPD2160	Approved
0.6171	Remote Similarity	NPD2626	Approved
0.6171	Remote Similarity	NPD2159	Approved
0.6171	Remote Similarity	NPD2627	Approved
0.6165	Remote Similarity	NPD2845	Phase 2
0.6165	Remote Similarity	NPD3321	Discontinued
0.6165	Remote Similarity	NPD2843	Phase 2
0.6162	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD5203	Approved
0.6158	Remote Similarity	NPD4617	Approved
0.6158	Remote Similarity	NPD2613	Approved
0.6158	Remote Similarity	NPD4620	Approved
0.6158	Remote Similarity	NPD5201	Approved
0.6154	Remote Similarity	NPD5150	Phase 2
0.6154	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7036	Phase 3
0.6154	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7035	Approved
0.615	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD7086	Phase 2
0.6142	Remote Similarity	NPD5186	Approved
0.6142	Remote Similarity	NPD5183	Approved
0.6141	Remote Similarity	NPD6681	Discovery
0.6141	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD3277	Phase 3
0.6137	Remote Similarity	NPD7560	Approved
0.6135	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD3912	Discontinued
0.6133	Remote Similarity	NPD7820	Phase 3
0.6127	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD4274	Approved
0.6124	Remote Similarity	NPD4275	Approved
0.6124	Remote Similarity	NPD3720	Discontinued
0.6121	Remote Similarity	NPD3802	Phase 3
0.6121	Remote Similarity	NPD5487	Phase 1
0.6121	Remote Similarity	NPD7205	Discontinued
0.6121	Remote Similarity	NPD6669	Phase 2
0.6116	Remote Similarity	NPD7805	Phase 3
0.6116	Remote Similarity	NPD8461	Discontinued
0.6114	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD5856	Discontinued
0.6114	Remote Similarity	NPD3125	Approved
0.6111	Remote Similarity	NPD5185	Approved
0.6111	Remote Similarity	NPD6310	Approved
0.6111	Remote Similarity	NPD6309	Approved
0.6111	Remote Similarity	NPD5184	Approved
0.6111	Remote Similarity	NPD2388	Discontinued
0.6111	Remote Similarity	NPD5182	Approved
0.6111	Remote Similarity	NPD6311	Approved
0.6111	Remote Similarity	NPD7043	Discontinued
0.6108	Remote Similarity	NPD5596	Phase 2
0.6106	Remote Similarity	NPD5214	Phase 2
0.6101	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD5444	Phase 1
0.6098	Remote Similarity	NPD3153	Approved
0.6098	Remote Similarity	NPD3154	Approved
0.6094	Remote Similarity	NPD6913	Approved
0.6094	Remote Similarity	NPD1663	Discontinued
0.6094	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD7891	Discontinued
0.6093	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD7396	Approved
0.6091	Remote Similarity	NPD7890	Discontinued
0.6091	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD8361	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