NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	3144.36
Volume:	3005.102
LogP:	-1.799
LogD:	3.784
LogS:	0.462
# Rotatable Bonds:	37
TPSA:	1266.48
# H-Bond Aceptor:	75
# H-Bond Donor:	45
# Rings:	9
# Heavy Atoms:	81

MedChem Properties

QED Drug-Likeness Score:	0.011
Synthetic Accessibility Score:	9.916
Fsp3:	0.615
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:	2.812
MDCK Permeability:	0.020090336
Pgp-inhibitor:	0
Pgp-substrate:	1
Human Intestinal Absorption (HIA):	1
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	1
Plasma Protein Binding (PPB):	25.83%
Volume Distribution (VD):	-1.834
Pgp-substrate:	70.99%

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):	-4.446
Half-life (T1/2):	0.55

ADMET: Toxicity

hERG Blockers:	0
Human Hepatotoxicity (H-HT):	1
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0
Rat Oral Acute Toxicity:	0
Maximum Recommended Daily Dose:	0
Skin Sensitization:	0.862
Carcinogencity:	0.012
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.845

Download Data

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

Natural Product: NPC477639

Natural Product ID:	NPC477639
*Common Name:**	Cycloviolin D
IUPAC Name:	3-[(1R,4S,7S,13R,16S,22S,28S,31S,34S,37R,40S,43S,46S,49S,52R,55S,58R,64S,67S,70S,73S,76S,79R,82S,88S,91S,94S)-43,49-bis(4-aminobutyl)-28,46-bis(2-amino-2-oxoethyl)-22,91-dibenzyl-64,76,88-tris[(2S)-butan-2-yl]-31-(3-carbamimidamidopropyl)-4,55,73-tris(hydroxymethyl)-34-[(4-hydroxyphenyl)methyl]-67,70-dimethyl-3,6,9,12,15,21,24,27,30,33,36,39,42,45,48,51,54,57,60,63,66,69,72,75,78,81,87,90,93,96-triacontaoxo-40,94-di(propan-2-yl)-2a,3a,6a,7a,98,99-hexathia-2,5,8,11,14,20,23,26,29,32,35,38,41,44,47,50,53,56,59,62,65,68,71,74,77,80,86,89,92,95-triacontazahexacyclo[50.44.4.413,58.437,79.016,20.082,86]octahectan-7-yl]propanoic acid
Synonyms:	Cycloviolin D
Standard InCHIKey:	WGVRHEXYCJCYCS-CMYGWODQSA-N
Standard InCHI:	InChI=1S/C135H205N37O38S6/c1-13-68(8)105-129(205)145-56-101(181)150-90-61-212-211-60-89-111(187)144-54-99(179)148-80(42-43-102(182)183)114(190)158-87(58-174)120(196)162-93-64-215-213-62-91(161-121(197)88(59-175)159-122(90)198)123(199)153-77(33-22-24-44-136)112(188)156-84(53-98(139)178)117(193)151-78(34-23-25-45-137)115(191)166-104(67(6)7)131(207)165-92(124(200)154-81(50-75-38-40-76(176)41-39-75)116(192)152-79(35-26-46-142-135(140)141)113(189)155-83(52-97(138)177)110(186)143-55-100(180)149-85(51-74-31-20-17-21-32-74)133(209)171-47-27-36-95(171)127(203)163-89)63-214-216-65-94(126(202)169-106(69(9)14-2)132(208)160-86(57-173)119(195)147-71(11)108(184)146-72(12)109(185)168-105)164-128(204)96-37-28-48-172(96)134(210)107(70(10)15-3)170-118(194)82(49-73-29-18-16-19-30-73)157-130(206)103(66(4)5)167-125(93)201/h16-21,29-32,38-41,66-72,77-96,103-107,173-176H,13-15,22-28,33-37,42-65,136-137H2,1-12H3,(H2,138,177)(H2,139,178)(H,143,186)(H,144,187)(H,145,205)(H,146,184)(H,147,195)(H,148,179)(H,149,180)(H,150,181)(H,151,193)(H,152,192)(H,153,199)(H,154,200)(H,155,189)(H,156,188)(H,157,206)(H,158,190)(H,159,198)(H,160,208)(H,161,197)(H,162,196)(H,163,203)(H,164,204)(H,165,207)(H,166,191)(H,167,201)(H,168,185)(H,169,202)(H,170,194)(H,182,183)(H4,140,141,142)/t68-,69-,70-,71-,72-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,103-,104-,105-,106-,107-/m0/s1
SMILES:	CC[C@H](C)[C@H]1C(=O)NCC(=O)N[C@H]2CSSC[C@H]3C(=O)NCC(=O)N[C@H](C(=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)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)C)C)CO)[C@@H](C)CC)NC(=O)[C@@H]5CCCN5C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC4=O)C(C)C)CC6=CC=CC=C6)[C@@H](C)CC)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N7CCC[C@H]7C(=O)N3)CC8=CC=CC=C8)CC(=O)N)CCCNC(=N)N)CC9=CC=C(C=C9)O)C(C)C)CCCCN)CC(=O)N)CCCCN)NC(=O)[C@@H](NC2=O)CO)CO)CCC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44592648
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 NPC477639 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	223
0.1-0.2	1240
0.2-0.3	6238
0.3-0.4	11761
0.4-0.5	18887
0.5-0.6	3542
0.6-0.7	545
0.7-0.8	198
0.8-0.85	34
0.85-0.9	7
0.9-0.95	10
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9713	High Similarity	NPC477631
0.9711	High Similarity	NPC477636
0.9382	High Similarity	NPC477632
0.9382	High Similarity	NPC477638
0.9195	High Similarity	NPC477637
0.8602	High Similarity	NPC329295
0.8251	Intermediate Similarity	NPC473404
0.8235	Intermediate Similarity	NPC61332
0.8235	Intermediate Similarity	NPC240130
0.8114	Intermediate Similarity	NPC326349
0.8114	Intermediate Similarity	NPC323336
0.8098	Intermediate Similarity	NPC153554
0.8045	Intermediate Similarity	NPC61004
0.8042	Intermediate Similarity	NPC60516
0.8041	Intermediate Similarity	NPC477551
0.8032	Intermediate Similarity	NPC94862
0.8011	Intermediate Similarity	NPC274198
0.8011	Intermediate Similarity	NPC198254
0.801	Intermediate Similarity	NPC302715
0.7989	Intermediate Similarity	NPC102959
0.7956	Intermediate Similarity	NPC280022
0.7946	Intermediate Similarity	NPC119652
0.7946	Intermediate Similarity	NPC97526
0.7938	Intermediate Similarity	NPC477552
0.7938	Intermediate Similarity	NPC477550
0.7935	Intermediate Similarity	NPC196243
0.7912	Intermediate Similarity	NPC276506
0.7869	Intermediate Similarity	NPC328494
0.7857	Intermediate Similarity	NPC129486
0.7826	Intermediate Similarity	NPC475532
0.7814	Intermediate Similarity	NPC475123
0.7814	Intermediate Similarity	NPC475204
0.7814	Intermediate Similarity	NPC46009
0.7802	Intermediate Similarity	NPC328649
0.7784	Intermediate Similarity	NPC471165
0.7784	Intermediate Similarity	NPC56685
0.7784	Intermediate Similarity	NPC165285
0.7784	Intermediate Similarity	NPC17698
0.7778	Intermediate Similarity	NPC241794
0.7761	Intermediate Similarity	NPC478005
0.773	Intermediate Similarity	NPC137627
0.773	Intermediate Similarity	NPC306804
0.7722	Intermediate Similarity	NPC469243
0.7697	Intermediate Similarity	NPC473580
0.7692	Intermediate Similarity	NPC223207
0.7684	Intermediate Similarity	NPC262166
0.7684	Intermediate Similarity	NPC202198
0.765	Intermediate Similarity	NPC304074
0.765	Intermediate Similarity	NPC471771
0.765	Intermediate Similarity	NPC290755
0.7624	Intermediate Similarity	NPC475544
0.7619	Intermediate Similarity	NPC475564
0.7619	Intermediate Similarity	NPC475409
0.7619	Intermediate Similarity	NPC170302
0.7598	Intermediate Similarity	NPC244509
0.7596	Intermediate Similarity	NPC63931
0.7578	Intermediate Similarity	NPC477635
0.7578	Intermediate Similarity	NPC477630
0.7569	Intermediate Similarity	NPC244336
0.7566	Intermediate Similarity	NPC194671
0.7566	Intermediate Similarity	NPC269750
0.7553	Intermediate Similarity	NPC50016
0.7514	Intermediate Similarity	NPC107938
0.7514	Intermediate Similarity	NPC294516
0.7513	Intermediate Similarity	NPC473546
0.75	Intermediate Similarity	NPC155506
0.75	Intermediate Similarity	NPC136797
0.75	Intermediate Similarity	NPC159767
0.75	Intermediate Similarity	NPC26108
0.7487	Intermediate Similarity	NPC89831
0.7476	Intermediate Similarity	NPC469445
0.7471	Intermediate Similarity	NPC77905
0.7451	Intermediate Similarity	NPC220060
0.7447	Intermediate Similarity	NPC273755
0.7441	Intermediate Similarity	NPC478007
0.7433	Intermediate Similarity	NPC40234
0.7419	Intermediate Similarity	NPC302597
0.7415	Intermediate Similarity	NPC469444
0.7413	Intermediate Similarity	NPC469443
0.7407	Intermediate Similarity	NPC473402
0.7407	Intermediate Similarity	NPC476227
0.7407	Intermediate Similarity	NPC279871
0.7401	Intermediate Similarity	NPC16188
0.7394	Intermediate Similarity	NPC230611
0.7389	Intermediate Similarity	NPC5194
0.7389	Intermediate Similarity	NPC261934
0.7382	Intermediate Similarity	NPC45037
0.7374	Intermediate Similarity	NPC473491
0.7371	Intermediate Similarity	NPC478008
0.7326	Intermediate Similarity	NPC141957
0.7303	Intermediate Similarity	NPC311658
0.7296	Intermediate Similarity	NPC96275
0.7282	Intermediate Similarity	NPC299806
0.7263	Intermediate Similarity	NPC248670
0.7238	Intermediate Similarity	NPC233702
0.7228	Intermediate Similarity	NPC324850
0.7225	Intermediate Similarity	NPC473354
0.7222	Intermediate Similarity	NPC51047
0.7216	Intermediate Similarity	NPC476321
0.7213	Intermediate Similarity	NPC476268
0.7196	Intermediate Similarity	NPC66490
0.7179	Intermediate Similarity	NPC470112
0.7179	Intermediate Similarity	NPC470903
0.7179	Intermediate Similarity	NPC167763
0.7159	Intermediate Similarity	NPC48202
0.7157	Intermediate Similarity	NPC473450
0.7151	Intermediate Similarity	NPC114806
0.7143	Intermediate Similarity	NPC63040
0.7143	Intermediate Similarity	NPC471048
0.7143	Intermediate Similarity	NPC294951
0.7143	Intermediate Similarity	NPC209463
0.7143	Intermediate Similarity	NPC471050
0.7143	Intermediate Similarity	NPC471049
0.7143	Intermediate Similarity	NPC300443
0.7136	Intermediate Similarity	NPC473305
0.7136	Intermediate Similarity	NPC163961
0.7135	Intermediate Similarity	NPC158277
0.7128	Intermediate Similarity	NPC472923
0.7119	Intermediate Similarity	NPC476989
0.7114	Intermediate Similarity	NPC328763
0.7104	Intermediate Similarity	NPC473341
0.7097	Intermediate Similarity	NPC1390
0.7097	Intermediate Similarity	NPC24617
0.7097	Intermediate Similarity	NPC62104
0.7095	Intermediate Similarity	NPC477634
0.7092	Intermediate Similarity	NPC471526
0.709	Intermediate Similarity	NPC15068
0.7085	Intermediate Similarity	NPC246591
0.7079	Intermediate Similarity	NPC80514
0.7079	Intermediate Similarity	NPC59827
0.7079	Intermediate Similarity	NPC184933
0.7075	Intermediate Similarity	NPC25539
0.7062	Intermediate Similarity	NPC214988
0.7047	Intermediate Similarity	NPC477462
0.7037	Intermediate Similarity	NPC5719
0.7037	Intermediate Similarity	NPC217804
0.7037	Intermediate Similarity	NPC22883
0.7037	Intermediate Similarity	NPC210377
0.7035	Intermediate Similarity	NPC4910
0.7033	Intermediate Similarity	NPC194699
0.7033	Intermediate Similarity	NPC219350
0.7026	Intermediate Similarity	NPC475421
0.7015	Intermediate Similarity	NPC470728
0.7006	Intermediate Similarity	NPC313694
0.7006	Intermediate Similarity	NPC242159
0.6981	Remote Similarity	NPC469442
0.6981	Remote Similarity	NPC277306
0.6976	Remote Similarity	NPC477527
0.6976	Remote Similarity	NPC323662
0.695	Remote Similarity	NPC329731
0.6944	Remote Similarity	NPC476978
0.6932	Remote Similarity	NPC141050
0.6927	Remote Similarity	NPC473000
0.6905	Remote Similarity	NPC246303
0.6902	Remote Similarity	NPC7817
0.6902	Remote Similarity	NPC475168
0.6889	Remote Similarity	NPC91953
0.6882	Remote Similarity	NPC470902
0.6878	Remote Similarity	NPC469901
0.6875	Remote Similarity	NPC328924
0.6868	Remote Similarity	NPC81026
0.6863	Remote Similarity	NPC65714
0.6863	Remote Similarity	NPC314083
0.6848	Remote Similarity	NPC2501
0.6847	Remote Similarity	NPC473378
0.6847	Remote Similarity	NPC248822
0.6847	Remote Similarity	NPC473407
0.6847	Remote Similarity	NPC323244
0.6847	Remote Similarity	NPC477526
0.6836	Remote Similarity	NPC267237
0.6833	Remote Similarity	NPC197921
0.6828	Remote Similarity	NPC122590
0.6813	Remote Similarity	NPC266741
0.6813	Remote Similarity	NPC315266
0.6796	Remote Similarity	NPC168861
0.6796	Remote Similarity	NPC473371
0.6796	Remote Similarity	NPC469360
0.6791	Remote Similarity	NPC39431
0.6776	Remote Similarity	NPC314358
0.6772	Remote Similarity	NPC197743
0.6772	Remote Similarity	NPC297145
0.6763	Remote Similarity	NPC471592
0.6758	Remote Similarity	NPC326241
0.6751	Remote Similarity	NPC469900
0.6736	Remote Similarity	NPC254700
0.6723	Remote Similarity	NPC326966
0.6722	Remote Similarity	NPC132636
0.6721	Remote Similarity	NPC313867
0.6721	Remote Similarity	NPC316008
0.6718	Remote Similarity	NPC196091
0.6685	Remote Similarity	NPC287401
0.6667	Remote Similarity	NPC186617
0.6667	Remote Similarity	NPC52748
0.6667	Remote Similarity	NPC326333
0.6667	Remote Similarity	NPC315283
0.6667	Remote Similarity	NPC477633
0.6667	Remote Similarity	NPC130309
0.6667	Remote Similarity	NPC469903
0.6667	Remote Similarity	NPC315388
0.6667	Remote Similarity	NPC314388

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 NPC477639 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	415
0.2-0.3	717
0.3-0.4	1963
0.4-0.5	3886
0.5-0.6	1828
0.6-0.7	194
0.7-0.8	8
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8146	Intermediate Similarity	NPD8303	Discontinued
0.7809	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7523	Phase 3
0.7569	Intermediate Similarity	NPD8019	Approved
0.7473	Intermediate Similarity	NPD7495	Discontinued
0.7249	Intermediate Similarity	NPD4652	Approved
0.7136	Intermediate Similarity	NPD7617	Discontinued
0.7079	Intermediate Similarity	NPD8076	Discontinued
0.7079	Intermediate Similarity	NPD7978	Discontinued
0.7037	Intermediate Similarity	NPD2098	Approved
0.7006	Intermediate Similarity	NPD6901	Phase 3
0.6973	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7303	Discontinued
0.6931	Remote Similarity	NPD2097	Approved
0.6872	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3136	Phase 2
0.6851	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD6796	Discontinued
0.6771	Remote Similarity	NPD8292	Phase 2
0.6769	Remote Similarity	NPD5137	Approved
0.676	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2889	Approved
0.6667	Remote Similarity	NPD2017	Approved
0.6667	Remote Similarity	NPD2888	Approved
0.6667	Remote Similarity	NPD2890	Approved
0.6648	Remote Similarity	NPD7450	Phase 2
0.6635	Remote Similarity	NPD6256	Approved
0.6635	Remote Similarity	NPD6255	Approved
0.6635	Remote Similarity	NPD6254	Approved
0.662	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6253	Approved
0.6578	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD8173	Phase 2
0.6575	Remote Similarity	NPD8172	Phase 2
0.6548	Remote Similarity	NPD7608	Discontinued
0.6536	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.653	Remote Similarity	NPD6189	Approved
0.653	Remote Similarity	NPD6188	Approved
0.6524	Remote Similarity	NPD7282	Approved
0.6524	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.652	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD7613	Discontinued
0.65	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6187	Approved
0.6464	Remote Similarity	NPD5323	Approved
0.6464	Remote Similarity	NPD8416	Discontinued
0.6452	Remote Similarity	NPD5265	Approved
0.6452	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5264	Approved
0.6449	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD8162	Phase 2
0.6448	Remote Similarity	NPD4126	Approved
0.6444	Remote Similarity	NPD1330	Phase 2
0.6444	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD4566	Approved
0.6443	Remote Similarity	NPD4567	Approved
0.6425	Remote Similarity	NPD4125	Approved
0.6419	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD7484	Phase 3
0.6414	Remote Similarity	NPD7485	Phase 3
0.6404	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5355	Approved
0.6392	Remote Similarity	NPD5356	Approved
0.6387	Remote Similarity	NPD7131	Phase 3
0.6385	Remote Similarity	NPD7810	Phase 3
0.6385	Remote Similarity	NPD7811	Phase 3
0.6364	Remote Similarity	NPD5076	Approved
0.6364	Remote Similarity	NPD5077	Approved
0.6354	Remote Similarity	NPD5299	Approved
0.6348	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD6390	Discontinued
0.6335	Remote Similarity	NPD3879	Approved
0.6296	Remote Similarity	NPD6863	Phase 2
0.6294	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.629	Remote Similarity	NPD3878	Approved
0.628	Remote Similarity	NPD6851	Approved
0.628	Remote Similarity	NPD6853	Approved
0.6275	Remote Similarity	NPD5484	Approved
0.6275	Remote Similarity	NPD5485	Approved
0.6263	Remote Similarity	NPD5219	Approved
0.6263	Remote Similarity	NPD5218	Approved
0.6256	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8643	Discontinued
0.6244	Remote Similarity	NPD6297	Approved
0.6238	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6836	Approved
0.6238	Remote Similarity	NPD7965	Phase 2
0.6232	Remote Similarity	NPD7281	Phase 3
0.6232	Remote Similarity	NPD7280	Phase 3
0.623	Remote Similarity	NPD5614	Approved
0.623	Remote Similarity	NPD3988	Approved
0.623	Remote Similarity	NPD3987	Approved
0.623	Remote Similarity	NPD5613	Approved
0.6216	Remote Similarity	NPD5725	Approved
0.6216	Remote Similarity	NPD6073	Approved
0.6209	Remote Similarity	NPD6505	Approved
0.6209	Remote Similarity	NPD6504	Approved
0.6209	Remote Similarity	NPD7283	Approved
0.6204	Remote Similarity	NPD8255	Phase 2
0.6202	Remote Similarity	NPD6557	Phase 2
0.6202	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD3125	Approved
0.6201	Remote Similarity	NPD5367	Discontinued
0.62	Remote Similarity	NPD7133	Discontinued
0.6196	Remote Similarity	NPD4153	Approved
0.6193	Remote Similarity	NPD4557	Approved
0.6188	Remote Similarity	NPD4177	Approved
0.6188	Remote Similarity	NPD4175	Approved
0.6188	Remote Similarity	NPD7827	Phase 1
0.6188	Remote Similarity	NPD3040	Approved
0.6181	Remote Similarity	NPD8031	Discontinued
0.6181	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.618	Remote Similarity	NPD3073	Approved
0.618	Remote Similarity	NPD3072	Approved
0.618	Remote Similarity	NPD3071	Approved
0.6173	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.617	Remote Similarity	NPD2088	Approved
0.617	Remote Similarity	NPD2087	Approved
0.6168	Remote Similarity	NPD3659	Discontinued
0.6158	Remote Similarity	NPD3400	Discontinued
0.6158	Remote Similarity	NPD8124	Phase 3
0.6158	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4676	Approved
0.6154	Remote Similarity	NPD5263	Approved
0.615	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD2517	Approved
0.6138	Remote Similarity	NPD6681	Discovery
0.6135	Remote Similarity	NPD4087	Phase 2
0.6135	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD2568	Approved
0.6124	Remote Similarity	NPD4761	Approved
0.6124	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD4762	Approved
0.612	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD6835	Approved
0.6114	Remote Similarity	NPD5851	Approved
0.6114	Remote Similarity	NPD5852	Approved
0.6096	Remote Similarity	NPD3552	Approved
0.6096	Remote Similarity	NPD3553	Approved
0.6096	Remote Similarity	NPD3555	Approved
0.6096	Remote Similarity	NPD3554	Approved
0.6094	Remote Similarity	NPD3510	Approved
0.6094	Remote Similarity	NPD3509	Approved
0.6089	Remote Similarity	NPD2584	Suspended
0.6089	Remote Similarity	NPD2516	Approved
0.6089	Remote Similarity	NPD2562	Approved
0.6089	Remote Similarity	NPD6304	Approved
0.6089	Remote Similarity	NPD6303	Approved
0.6089	Remote Similarity	NPD2561	Approved
0.6087	Remote Similarity	NPD3518	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.608	Remote Similarity	NPD5967	Approved
0.6075	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD5037	Approved
0.6066	Remote Similarity	NPD5038	Approved
0.6064	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD6088	Approved
0.6062	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD7970	Approved
0.6062	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD9568	Approved
0.6054	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD5747	Discontinued
0.6053	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD2437	Approved
0.6053	Remote Similarity	NPD2436	Approved
0.6051	Remote Similarity	NPD1670	Discontinued
0.6044	Remote Similarity	NPD7451	Discontinued
0.6044	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD8323	Discontinued
0.6038	Remote Similarity	NPD4435	Approved
0.6038	Remote Similarity	NPD4157	Discontinued
0.6036	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD9570	Approved
0.603	Remote Similarity	NPD7972	Discontinued
0.6029	Remote Similarity	NPD5034	Approved
0.6029	Remote Similarity	NPD4954	Approved
0.6029	Remote Similarity	NPD4955	Approved
0.6029	Remote Similarity	NPD36	Approved
0.6029	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD5026	Approved
0.6029	Remote Similarity	NPD5028	Approved
0.6027	Remote Similarity	NPD2853	Approved
0.6022	Remote Similarity	NPD6346	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