NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	2884.11
Volume:	2713.727
LogP:	-1.307
LogD:	3.736
LogS:	0.836
# Rotatable Bonds:	29
TPSA:	1206.58
# H-Bond Aceptor:	71
# H-Bond Donor:	42
# Rings:	9
# Heavy Atoms:	77

MedChem Properties

QED Drug-Likeness Score:	0.01
Synthetic Accessibility Score:	9.803
Fsp3:	0.592
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	2.602
MDCK Permeability:	0.030302923
Pgp-inhibitor:	0
Pgp-substrate:	1
Human Intestinal Absorption (HIA):	1
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	1

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	1
Plasma Protein Binding (PPB):	16.62%
Volume Distribution (VD):	-1.951
Pgp-substrate:	61.34%

ADMET: Metabolism

CYP1A2-inhibitor:	0
CYP1A2-substrate:	0
CYP2C19-inhibitor:	0
CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0
CYP2C9-substrate:	0
CYP2D6-inhibitor:	0
CYP2D6-substrate:	0
CYP3A4-inhibitor:	0
CYP3A4-substrate:	0

ADMET: Excretion

Clearance (CL):	-4.189
Half-life (T1/2):	0.769

ADMET: Toxicity

hERG Blockers:	0
Human Hepatotoxicity (H-HT):	1
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0
Rat Oral Acute Toxicity:	0
Maximum Recommended Daily Dose:	0
Skin Sensitization:	0.847
Carcinogencity:	0.001
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.871

Download Data

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

Natural Product: NPC477637

Natural Product ID:	NPC477637
*Common Name:**	Cycloviolin B
IUPAC Name:	3-[(1R,7S,10S,13R,16S,19S,22S,28S,31R,34S,37S,40S,46R,49S,52R,55S,58S,61S,64S,67R,70S,73S,76S,82S,85S)-73-(4-aminobutyl)-76-(2-amino-2-oxoethyl)-64-(3-amino-3-oxopropyl)-34,70-dibenzyl-37,49,55,82-tetrakis[(1R)-1-hydroxyethyl]-10,58,61-tris(hydroxymethyl)-16-[(4-hydroxyphenyl)methyl]-85-methyl-22-(2-methylpropyl)-2,5,8,11,14,17,20,23,29,32,35,38,41,44,47,50,53,56,59,62,65,68,71,74,77,80,83,86-octacosaoxo-19,40-di(propan-2-yl)-89,90,93,94,97,98-hexathia-3,6,9,12,15,18,21,24,30,33,36,39,42,45,48,51,54,57,60,63,66,69,72,75,78,81,84,87-octacosazapentacyclo[44.41.4.413,52.431,67.024,28]nonanonacontan-7-yl]propanoic acid
Synonyms:
Standard InCHIKey:	HLXPUKTVQPHDNH-JIQJZISXSA-N
Standard InCHI:	InChI=1S/C120H177N31O40S6/c1-54(2)37-73-120(191)151-36-20-26-83(151)113(184)143-81-52-196-194-50-79-108(179)132-69(38-62-21-14-12-15-22-62)102(173)130-66(25-18-19-35-121)99(170)135-72(41-85(123)161)97(168)124-44-88(164)145-92(58(8)155)116(187)127-57(7)96(167)140-77-48-192-193-49-78(129-87(163)43-126-114(185)90(55(3)4)147-119(190)95(61(11)158)148-104(175)70(133-110(81)181)39-63-23-16-13-17-24-63)111(182)149-94(60(10)157)118(189)144-82(112(183)150-93(59(9)156)117(188)139-76(47-154)106(177)138-74(45-152)105(176)131-68(101(172)141-79)31-33-84(122)160)53-197-195-51-80(142-107(178)75(46-153)137-100(171)67(32-34-89(165)166)128-86(162)42-125-98(77)169)109(180)134-71(40-64-27-29-65(159)30-28-64)103(174)146-91(56(5)6)115(186)136-73/h12-17,21-24,27-30,54-61,66-83,90-95,152-159H,18-20,25-26,31-53,121H2,1-11H3,(H2,122,160)(H2,123,161)(H,124,168)(H,125,169)(H,126,185)(H,127,187)(H,128,162)(H,129,163)(H,130,173)(H,131,176)(H,132,179)(H,133,181)(H,134,180)(H,135,170)(H,136,186)(H,137,171)(H,138,177)(H,139,188)(H,140,167)(H,141,172)(H,142,178)(H,143,184)(H,144,189)(H,145,164)(H,146,174)(H,147,190)(H,148,175)(H,149,182)(H,150,183)(H,165,166)/t57-,58+,59+,60+,61+,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,90-,91-,92-,93-,94-,95-/m0/s1
SMILES:	C[C@H]1C(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@H](C(=O)N[C@H]4CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N5CCC[C@H]5C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N1)[C@@H](C)O)CC(=O)N)CCCCN)CC6=CC=CC=C6)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC4=O)[C@@H](C)O)CO)CO)CCC(=O)N)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N3)C(C)C)[C@@H](C)O)CC7=CC=CC=C7)CC(C)C)C(C)C)CC8=CC=C(C=C8)O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC2=O)CCC(=O)O)CO)[C@@H](C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44592646
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0003297] Organic Polymers [CHEMONTID:0003298] Polypeptides

*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
NPO33585	Palicourea condensata	Species	Rubiaceae	Eukaryota	Bark	Pastaza, Ecuador	1988-MAR	PMID[11430013]

☑ 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
EC50	2
IC50	1

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	50	nM	PMID[11430013]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	130	nM	PMID[20718473]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	560	nM	PMID[20718473]

☑ 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 NPC477637 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	185
0.1-0.2	1109
0.2-0.3	4785
0.3-0.4	12614
0.4-0.5	17275
0.5-0.6	5679
0.6-0.7	711
0.7-0.8	257
0.8-0.85	47
0.85-0.9	20
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9244	High Similarity	NPC477631
0.9195	High Similarity	NPC477639
0.9128	High Similarity	NPC477636
0.892	High Similarity	NPC477632
0.892	High Similarity	NPC477638
0.8712	High Similarity	NPC323336
0.8712	High Similarity	NPC326349
0.8623	High Similarity	NPC61004
0.8471	Intermediate Similarity	NPC475123
0.8471	Intermediate Similarity	NPC475204
0.8471	Intermediate Similarity	NPC46009
0.843	Intermediate Similarity	NPC471165
0.8208	Intermediate Similarity	NPC328494
0.8171	Intermediate Similarity	NPC50016
0.8161	Intermediate Similarity	NPC306804
0.8161	Intermediate Similarity	NPC137627
0.8152	Intermediate Similarity	NPC329295
0.8144	Intermediate Similarity	NPC244509
0.814	Intermediate Similarity	NPC328649
0.814	Intermediate Similarity	NPC107938
0.814	Intermediate Similarity	NPC294516
0.8107	Intermediate Similarity	NPC244336
0.809	Intermediate Similarity	NPC473404
0.8057	Intermediate Similarity	NPC273755
0.8046	Intermediate Similarity	NPC40234
0.8024	Intermediate Similarity	NPC56685
0.8023	Intermediate Similarity	NPC63931
0.8011	Intermediate Similarity	NPC473402
0.8	Intermediate Similarity	NPC230611
0.7978	Intermediate Similarity	NPC269750
0.7978	Intermediate Similarity	NPC45037
0.7978	Intermediate Similarity	NPC194671
0.7917	Intermediate Similarity	NPC262166
0.791	Intermediate Similarity	NPC476227
0.791	Intermediate Similarity	NPC155506
0.791	Intermediate Similarity	NPC26108
0.791	Intermediate Similarity	NPC159767
0.7904	Intermediate Similarity	NPC473491
0.7898	Intermediate Similarity	NPC89831
0.788	Intermediate Similarity	NPC60516
0.788	Intermediate Similarity	NPC240130
0.788	Intermediate Similarity	NPC61332
0.7853	Intermediate Similarity	NPC248670
0.7826	Intermediate Similarity	NPC102959
0.7824	Intermediate Similarity	NPC476268
0.7809	Intermediate Similarity	NPC279871
0.7809	Intermediate Similarity	NPC473354
0.7803	Intermediate Similarity	NPC241794
0.779	Intermediate Similarity	NPC476321
0.7727	Intermediate Similarity	NPC302597
0.7725	Intermediate Similarity	NPC16188
0.7709	Intermediate Similarity	NPC158277
0.7706	Intermediate Similarity	NPC473341
0.7706	Intermediate Similarity	NPC202198
0.7696	Intermediate Similarity	NPC477551
0.7676	Intermediate Similarity	NPC94862
0.766	Intermediate Similarity	NPC302715
0.765	Intermediate Similarity	NPC471526
0.7637	Intermediate Similarity	NPC153554
0.7636	Intermediate Similarity	NPC476989
0.7611	Intermediate Similarity	NPC136797
0.7602	Intermediate Similarity	NPC5194
0.7602	Intermediate Similarity	NPC261934
0.7592	Intermediate Similarity	NPC477550
0.7592	Intermediate Similarity	NPC477552
0.759	Intermediate Similarity	NPC77905
0.7584	Intermediate Similarity	NPC280022
0.7582	Intermediate Similarity	NPC119652
0.7582	Intermediate Similarity	NPC97526
0.7568	Intermediate Similarity	NPC299806
0.7544	Intermediate Similarity	NPC233702
0.7543	Intermediate Similarity	NPC469243
0.7542	Intermediate Similarity	NPC198254
0.7542	Intermediate Similarity	NPC274198
0.7528	Intermediate Similarity	NPC209463
0.7514	Intermediate Similarity	NPC471048
0.7514	Intermediate Similarity	NPC473580
0.7514	Intermediate Similarity	NPC294951
0.7514	Intermediate Similarity	NPC223207
0.7514	Intermediate Similarity	NPC471049
0.7514	Intermediate Similarity	NPC471050
0.7513	Intermediate Similarity	NPC478005
0.75	Intermediate Similarity	NPC473305
0.75	Intermediate Similarity	NPC163961
0.7486	Intermediate Similarity	NPC129486
0.7485	Intermediate Similarity	NPC91953
0.7485	Intermediate Similarity	NPC475168
0.7485	Intermediate Similarity	NPC7817
0.7474	Intermediate Similarity	NPC328763
0.7473	Intermediate Similarity	NPC196243
0.7472	Intermediate Similarity	NPC290755
0.7472	Intermediate Similarity	NPC304074
0.7472	Intermediate Similarity	NPC471771
0.7459	Intermediate Similarity	NPC475532
0.7457	Intermediate Similarity	NPC470902
0.7456	Intermediate Similarity	NPC81026
0.7444	Intermediate Similarity	NPC276506
0.7443	Intermediate Similarity	NPC475544
0.7425	Intermediate Similarity	NPC197921
0.7418	Intermediate Similarity	NPC165285
0.7418	Intermediate Similarity	NPC17698
0.7416	Intermediate Similarity	NPC472923
0.7396	Intermediate Similarity	NPC266741
0.7391	Intermediate Similarity	NPC475421
0.7382	Intermediate Similarity	NPC65714
0.7381	Intermediate Similarity	NPC469360
0.7368	Intermediate Similarity	NPC248822
0.7368	Intermediate Similarity	NPC473378
0.7368	Intermediate Similarity	NPC473407
0.7356	Intermediate Similarity	NPC39431
0.7351	Intermediate Similarity	NPC475409
0.7351	Intermediate Similarity	NPC170302
0.7351	Intermediate Similarity	NPC475564
0.7344	Intermediate Similarity	NPC59827
0.7344	Intermediate Similarity	NPC184933
0.7333	Intermediate Similarity	NPC141957
0.732	Intermediate Similarity	NPC323662
0.7313	Intermediate Similarity	NPC469445
0.7306	Intermediate Similarity	NPC473371
0.7305	Intermediate Similarity	NPC242159
0.7305	Intermediate Similarity	NPC313694
0.7302	Intermediate Similarity	NPC4910
0.7286	Intermediate Similarity	NPC220060
0.7278	Intermediate Similarity	NPC254700
0.7273	Intermediate Similarity	NPC470112
0.7273	Intermediate Similarity	NPC167763
0.7273	Intermediate Similarity	NPC470903
0.7268	Intermediate Similarity	NPC471592
0.725	Intermediate Similarity	NPC469444
0.7245	Intermediate Similarity	NPC469443
0.7243	Intermediate Similarity	NPC473546
0.7236	Intermediate Similarity	NPC246303
0.7231	Intermediate Similarity	NPC477527
0.7225	Intermediate Similarity	NPC2501
0.7212	Intermediate Similarity	NPC326966
0.7211	Intermediate Similarity	NPC329731
0.7202	Intermediate Similarity	NPC314083
0.72	Intermediate Similarity	NPC122590
0.7198	Intermediate Similarity	NPC186617
0.7198	Intermediate Similarity	NPC478007
0.7188	Intermediate Similarity	NPC477526
0.7158	Intermediate Similarity	NPC471568
0.7158	Intermediate Similarity	NPC473693
0.7157	Intermediate Similarity	NPC473450
0.7143	Intermediate Similarity	NPC64205
0.7135	Intermediate Similarity	NPC197743
0.7135	Intermediate Similarity	NPC477462
0.7135	Intermediate Similarity	NPC297145
0.7129	Intermediate Similarity	NPC478008
0.712	Intermediate Similarity	NPC96275
0.7117	Intermediate Similarity	NPC477635
0.7117	Intermediate Similarity	NPC477630
0.7104	Intermediate Similarity	NPC315388
0.7104	Intermediate Similarity	NPC473000
0.7093	Intermediate Similarity	NPC322878
0.7093	Intermediate Similarity	NPC315266
0.7065	Intermediate Similarity	NPC196091
0.7059	Intermediate Similarity	NPC239762
0.7059	Intermediate Similarity	NPC163392
0.7056	Intermediate Similarity	NPC471527
0.7047	Intermediate Similarity	NPC51047
0.7035	Intermediate Similarity	NPC476978
0.7035	Intermediate Similarity	NPC52748
0.7024	Intermediate Similarity	NPC141050
0.6994	Remote Similarity	NPC471680
0.6988	Remote Similarity	NPC300315
0.6976	Remote Similarity	NPC326333
0.6966	Remote Similarity	NPC476742
0.6964	Remote Similarity	NPC287401
0.6961	Remote Similarity	NPC114806
0.6957	Remote Similarity	NPC473502
0.6957	Remote Similarity	NPC63040
0.6954	Remote Similarity	NPC314358
0.6949	Remote Similarity	NPC300443
0.6949	Remote Similarity	NPC162104
0.6941	Remote Similarity	NPC471264
0.6941	Remote Similarity	NPC471265
0.6941	Remote Similarity	NPC6570
0.6933	Remote Similarity	NPC46427
0.6933	Remote Similarity	NPC6975
0.6927	Remote Similarity	NPC476741
0.6927	Remote Similarity	NPC315542
0.6914	Remote Similarity	NPC311658
0.6908	Remote Similarity	NPC25539
0.6908	Remote Similarity	NPC326027
0.6907	Remote Similarity	NPC246591
0.6906	Remote Similarity	NPC1390
0.6906	Remote Similarity	NPC287757
0.6906	Remote Similarity	NPC62104
0.6906	Remote Similarity	NPC319320
0.6906	Remote Similarity	NPC24617
0.6904	Remote Similarity	NPC80514
0.6902	Remote Similarity	NPC15068
0.6897	Remote Similarity	NPC316008
0.6897	Remote Similarity	NPC313867
0.6893	Remote Similarity	NPC476743
0.6886	Remote Similarity	NPC325651
0.6885	Remote Similarity	NPC133470
0.6885	Remote Similarity	NPC289776
0.6885	Remote Similarity	NPC191863

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 NPC477637 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	124
0.1-0.2	419
0.2-0.3	728
0.3-0.4	1884
0.4-0.5	3507
0.5-0.6	2080
0.6-0.7	386
0.7-0.8	22
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
0.7941	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD8303	Discontinued
0.774	Intermediate Similarity	NPD4652	Approved
0.7697	Intermediate Similarity	NPD7978	Discontinued
0.7514	Intermediate Similarity	NPD2098	Approved
0.7442	Intermediate Similarity	NPD7303	Discontinued
0.7401	Intermediate Similarity	NPD2097	Approved
0.7362	Intermediate Similarity	NPD3136	Phase 2
0.7262	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7523	Phase 3
0.7126	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD2890	Approved
0.7104	Intermediate Similarity	NPD2888	Approved
0.7104	Intermediate Similarity	NPD2017	Approved
0.7104	Intermediate Similarity	NPD2889	Approved
0.7095	Intermediate Similarity	NPD8019	Approved
0.7029	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5137	Approved
0.7	Intermediate Similarity	NPD7495	Discontinued
0.6964	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD8172	Phase 2
0.6941	Remote Similarity	NPD8173	Phase 2
0.6919	Remote Similarity	NPD7450	Phase 2
0.6905	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1330	Phase 2
0.6856	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7613	Discontinued
0.6842	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7485	Phase 3
0.6828	Remote Similarity	NPD7484	Phase 3
0.6807	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7608	Discontinued
0.6782	Remote Similarity	NPD8076	Discontinued
0.6725	Remote Similarity	NPD5323	Approved
0.6705	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7617	Discontinued
0.6686	Remote Similarity	NPD4125	Approved
0.6685	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7810	Phase 3
0.6683	Remote Similarity	NPD7811	Phase 3
0.6647	Remote Similarity	NPD3125	Approved
0.663	Remote Similarity	NPD7131	Phase 3
0.6628	Remote Similarity	NPD8416	Discontinued
0.6618	Remote Similarity	NPD6255	Approved
0.6618	Remote Similarity	NPD6256	Approved
0.6618	Remote Similarity	NPD6254	Approved
0.6608	Remote Similarity	NPD5299	Approved
0.6597	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7133	Discontinued
0.6591	Remote Similarity	NPD2088	Approved
0.6591	Remote Similarity	NPD2087	Approved
0.6578	Remote Similarity	NPD8031	Discontinued
0.6575	Remote Similarity	NPD6390	Discontinued
0.6575	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6253	Approved
0.6568	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD2568	Approved
0.6548	Remote Similarity	NPD5367	Discontinued
0.6541	Remote Similarity	NPD5355	Approved
0.6541	Remote Similarity	NPD5356	Approved
0.6527	Remote Similarity	NPD2562	Approved
0.6527	Remote Similarity	NPD2561	Approved
0.6526	Remote Similarity	NPD2517	Approved
0.6519	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD3553	Approved
0.6514	Remote Similarity	NPD3554	Approved
0.6514	Remote Similarity	NPD6901	Phase 3
0.6514	Remote Similarity	NPD3552	Approved
0.6514	Remote Similarity	NPD3555	Approved
0.6509	Remote Similarity	NPD6188	Approved
0.6509	Remote Similarity	NPD6189	Approved
0.6505	Remote Similarity	NPD4557	Approved
0.65	Remote Similarity	NPD5076	Approved
0.65	Remote Similarity	NPD5077	Approved
0.6497	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5484	Approved
0.6495	Remote Similarity	NPD5485	Approved
0.6489	Remote Similarity	NPD5218	Approved
0.6489	Remote Similarity	NPD5219	Approved
0.648	Remote Similarity	NPD6676	Phase 2
0.648	Remote Similarity	NPD3400	Discontinued
0.6477	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD2516	Approved
0.6471	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7451	Discontinued
0.6462	Remote Similarity	NPD6187	Approved
0.6461	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD6681	Discovery
0.6453	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6796	Discontinued
0.6445	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6346	Approved
0.6425	Remote Similarity	NPD5264	Approved
0.6425	Remote Similarity	NPD5265	Approved
0.6422	Remote Similarity	NPD7282	Approved
0.642	Remote Similarity	NPD4126	Approved
0.6417	Remote Similarity	NPD5773	Approved
0.6417	Remote Similarity	NPD5772	Approved
0.6414	Remote Similarity	NPD6853	Approved
0.6414	Remote Similarity	NPD6851	Approved
0.6413	Remote Similarity	NPD4648	Approved
0.6413	Remote Similarity	NPD4646	Approved
0.6413	Remote Similarity	NPD4647	Approved
0.6404	Remote Similarity	NPD2022	Approved
0.6402	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8643	Discontinued
0.64	Remote Similarity	NPD4435	Approved
0.64	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5230	Approved
0.6393	Remote Similarity	NPD5229	Approved
0.6391	Remote Similarity	NPD4659	Approved
0.6378	Remote Similarity	NPD6297	Approved
0.6374	Remote Similarity	NPD2014	Approved
0.6374	Remote Similarity	NPD2016	Approved
0.6374	Remote Similarity	NPD2013	Approved
0.6373	Remote Similarity	NPD8124	Phase 3
0.6373	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD2853	Approved
0.6364	Remote Similarity	NPD16	Approved
0.6364	Remote Similarity	NPD318	Approved
0.6364	Remote Similarity	NPD5314	Approved
0.6364	Remote Similarity	NPD317	Approved
0.6364	Remote Similarity	NPD6073	Approved
0.6364	Remote Similarity	NPD856	Approved
0.6358	Remote Similarity	NPD2043	Approved
0.6358	Remote Similarity	NPD2045	Approved
0.6358	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD2051	Approved
0.6358	Remote Similarity	NPD21	Approved
0.6358	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD2044	Approved
0.6358	Remote Similarity	NPD2046	Approved
0.6358	Remote Similarity	NPD2048	Approved
0.6358	Remote Similarity	NPD2047	Approved
0.6354	Remote Similarity	NPD8323	Discontinued
0.635	Remote Similarity	NPD4434	Approved
0.635	Remote Similarity	NPD5037	Approved
0.635	Remote Similarity	NPD5038	Approved
0.6348	Remote Similarity	NPD9570	Approved
0.6344	Remote Similarity	NPD2891	Approved
0.6337	Remote Similarity	NPD6505	Approved
0.6337	Remote Similarity	NPD6504	Approved
0.6337	Remote Similarity	NPD4177	Approved
0.6337	Remote Similarity	NPD4175	Approved
0.6331	Remote Similarity	NPD3072	Approved
0.6331	Remote Similarity	NPD2584	Suspended
0.6331	Remote Similarity	NPD3073	Approved
0.6331	Remote Similarity	NPD3071	Approved
0.6322	Remote Similarity	NPD598	Approved
0.6322	Remote Similarity	NPD601	Approved
0.6322	Remote Similarity	NPD597	Approved
0.6316	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4103	Phase 2
0.6313	Remote Similarity	NPD36	Approved
0.6313	Remote Similarity	NPD5028	Approved
0.6313	Remote Similarity	NPD4954	Approved
0.6313	Remote Similarity	NPD5034	Approved
0.6313	Remote Similarity	NPD4955	Approved
0.6313	Remote Similarity	NPD5026	Approved
0.631	Remote Similarity	NPD2513	Approved
0.6306	Remote Similarity	NPD8292	Phase 2
0.6303	Remote Similarity	NPD9568	Approved
0.6301	Remote Similarity	NPD5263	Approved
0.63	Remote Similarity	NPD5036	Approved
0.6298	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7738	Approved
0.6296	Remote Similarity	NPD7737	Approved
0.6289	Remote Similarity	NPD7965	Phase 2
0.6289	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD1136	Approved
0.6286	Remote Similarity	NPD5745	Approved
0.6286	Remote Similarity	NPD1132	Approved
0.6286	Remote Similarity	NPD1130	Approved
0.6284	Remote Similarity	NPD5614	Approved
0.6284	Remote Similarity	NPD5613	Approved
0.6281	Remote Similarity	NPD5035	Approved
0.6281	Remote Similarity	NPD7280	Phase 3
0.6281	Remote Similarity	NPD7281	Phase 3
0.6279	Remote Similarity	NPD602	Approved
0.6279	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD599	Approved
0.6278	Remote Similarity	NPD2437	Approved
0.6278	Remote Similarity	NPD2436	Approved
0.6277	Remote Similarity	NPD2515	Approved
0.6277	Remote Similarity	NPD3007	Approved
0.6277	Remote Similarity	NPD4227	Discontinued
0.6272	Remote Similarity	NPD4762	Approved
0.6272	Remote Similarity	NPD4761	Approved
0.6271	Remote Similarity	NPD5725	Approved
0.6271	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.627	Remote Similarity	NPD1670	Discontinued
0.6264	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5030	Phase 2
0.625	Remote Similarity	NPD3061	Approved
0.625	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3062	Approved
0.625	Remote Similarity	NPD3158	Phase 1

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