NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	3099.36
Volume:	2952.813
LogP:	-1.42
LogD:	2.808
LogS:	0.401
# Rotatable Bonds:	36
TPSA:	1262.86
# H-Bond Aceptor:	75
# H-Bond Donor:	45
# Rings:	9
# Heavy Atoms:	81

MedChem Properties

QED Drug-Likeness Score:	0.01
Synthetic Accessibility Score:	9.907
Fsp3:	0.656
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:	2.265
MDCK Permeability:	0.018354541
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):	19.77%
Volume Distribution (VD):	-1.849
Pgp-substrate:	55.10%

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):	-3.815
Half-life (T1/2):	0.626

ADMET: Toxicity

hERG Blockers:	0
Human Hepatotoxicity (H-HT):	1
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0
Rat Oral Acute Toxicity:	0
Maximum Recommended Daily Dose:	0
Skin Sensitization:	0.692
Carcinogencity:	0.001
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC477632

Natural Product ID:	NPC477632
*Common Name:**	Circulin C
IUPAC Name:	n.a.
Synonyms:	Circulin C
Standard InCHIKey:	KNNKLNZUUUBNAO-KERYQHGTSA-N
Standard InCHI:	InChI=1S/C131H206N36O39S6/c1-15-65(10)100-127(203)165-103(69(14)172)128(204)153-83(55-171)116(192)161-97(62(4)5)124(200)141-68(13)104(180)138-49-94(176)143-85-57-208-207-56-84-106(182)140-50-93(175)142-76(39-40-96(178)179)109(185)151-81(53-169)114(190)155-88-60-211-209-58-86(154-115(191)82(54-170)152-117(85)193)118(194)146-73(30-21-23-41-132)108(184)150-80(52-168)113(189)145-74(31-22-24-42-133)110(186)160-99(64(8)9)126(202)158-87(59-210-212-61-89(121(197)163-100)157-123(199)91-34-27-45-167(91)130(206)102(67(12)17-3)164-112(188)78(46-70-28-19-18-20-29-70)149-125(201)98(63(6)7)162-120(88)196)119(195)147-77(47-71-35-37-72(173)38-36-71)111(187)144-75(32-25-43-137-131(135)136)107(183)148-79(48-92(134)174)105(181)139-51-95(177)159-101(66(11)16-2)129(205)166-44-26-33-90(166)122(198)156-84/h18-20,28-29,35-38,62-69,73-91,97-103,168-173H,15-17,21-27,30-34,39-61,132-133H2,1-14H3,(H2,134,174)(H,138,180)(H,139,181)(H,140,182)(H,141,200)(H,142,175)(H,143,176)(H,144,187)(H,145,189)(H,146,194)(H,147,195)(H,148,183)(H,149,201)(H,150,184)(H,151,185)(H,152,193)(H,153,204)(H,154,191)(H,155,190)(H,156,198)(H,157,199)(H,158,202)(H,159,177)(H,160,186)(H,161,192)(H,162,196)(H,163,197)(H,164,188)(H,165,203)(H,178,179)(H4,135,136,137)/t65-,66-,67+,68-,69+,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,97-,98-,99-,100-,101-,102-,103-/m0/s1
SMILES:	NCCCC[C@@H]1N=C(O)[C@@H]2CSSC[C@@H]3N=C(O)[C@H](CO)N=C(O)[C@H](CCC(=O)O)N=C(O)CN=C([C@@H]4CSSC[C@@H](C(=N[C@H](C(=N2)O)CO)O)N=C(O)CN=C(O)[C@H](C)N=C(O)[C@@H](N=C(O)[C@H](CO)N=C([C@@H](N=C([C@@H](N=C([C@H](CSSC[C@H](N=C([C@@H](N=C([C@@H](N=C([C@@H](N=C1O)CO)O)CCCCN)O)C(C)C)O)C(=N[C@@H](Cc1ccc(cc1)O)C(=N[C@@H](CCCNC(=N)N)C(=N[C@@H](CC(=N)O)C(=NCC(=N[C@H](C(=O)N1[C@H](C(=N4)O)CCC1)[C@H](CC)C)O)O)O)O)O)N=C([C@H]1N(C(=O)[C@@H](N=C([C@@H](N=C([C@@H](N=C3O)C(C)C)O)Cc2ccccc2)O)[C@@H](CC)C)CCC1)O)O)[C@H](CC)C)O)[C@H](O)C)O)C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL525248
PubChem CID:	44575206
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
NPO40066	Chassalia parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691702]
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	14
IC50	1

Activity Type	# Activity
Organism	15

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	=	73.0	nM	PMID[536273]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	165.0	nM	PMID[536273]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	213.0	nM	PMID[536273]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	155.0	nM	PMID[536273]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	111.0	nM	PMID[536273]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	51.0	nM	PMID[536273]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	241.0	nM	PMID[536273]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	247.0	nM	PMID[536273]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	67.0	nM	PMID[536273]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	48.0	nM	PMID[536273]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	200.0	nM	PMID[536273]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	50.0	nM	PMID[536274]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	40.0	nM	PMID[536275]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	40.0	nM	PMID[536276]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	500.0	nM	PMID[536276]

☑ 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 NPC477632 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	212
0.1-0.2	1218
0.2-0.3	6427
0.3-0.4	11791
0.4-0.5	18947
0.5-0.6	3314
0.6-0.7	485
0.7-0.8	235
0.8-0.85	39
0.85-0.9	9
0.9-0.95	6
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477638
0.9655	High Similarity	NPC477631
0.954	High Similarity	NPC477636
0.9382	High Similarity	NPC477639
0.9061	High Similarity	NPC329295
0.892	High Similarity	NPC477637
0.8603	High Similarity	NPC473404
0.8506	High Similarity	NPC61004
0.8478	Intermediate Similarity	NPC240130
0.8478	Intermediate Similarity	NPC61332
0.8378	Intermediate Similarity	NPC60516
0.8372	Intermediate Similarity	NPC323336
0.8372	Intermediate Similarity	NPC326349
0.8343	Intermediate Similarity	NPC153554
0.8324	Intermediate Similarity	NPC471165
0.8324	Intermediate Similarity	NPC102959
0.8305	Intermediate Similarity	NPC280022
0.827	Intermediate Similarity	NPC94862
0.8258	Intermediate Similarity	NPC274198
0.8258	Intermediate Similarity	NPC198254
0.8245	Intermediate Similarity	NPC302715
0.8212	Intermediate Similarity	NPC328494
0.8187	Intermediate Similarity	NPC119652
0.8187	Intermediate Similarity	NPC97526
0.8177	Intermediate Similarity	NPC477551
0.8167	Intermediate Similarity	NPC475532
0.8156	Intermediate Similarity	NPC46009
0.8156	Intermediate Similarity	NPC475204
0.8156	Intermediate Similarity	NPC475123
0.8156	Intermediate Similarity	NPC276506
0.8122	Intermediate Similarity	NPC17698
0.8122	Intermediate Similarity	NPC165285
0.8077	Intermediate Similarity	NPC196243
0.8073	Intermediate Similarity	NPC477550
0.8073	Intermediate Similarity	NPC477552
0.8043	Intermediate Similarity	NPC475564
0.8043	Intermediate Similarity	NPC170302
0.8043	Intermediate Similarity	NPC475409
0.8035	Intermediate Similarity	NPC56685
0.8023	Intermediate Similarity	NPC241794
0.8011	Intermediate Similarity	NPC244336
0.8	Intermediate Similarity	NPC129486
0.798	Intermediate Similarity	NPC478005
0.7978	Intermediate Similarity	NPC50016
0.7967	Intermediate Similarity	NPC306804
0.7967	Intermediate Similarity	NPC137627
0.7966	Intermediate Similarity	NPC469243
0.7944	Intermediate Similarity	NPC107938
0.7944	Intermediate Similarity	NPC294516
0.7944	Intermediate Similarity	NPC328649
0.7944	Intermediate Similarity	NPC302597
0.7935	Intermediate Similarity	NPC473546
0.7933	Intermediate Similarity	NPC63931
0.7931	Intermediate Similarity	NPC202198
0.7931	Intermediate Similarity	NPC262166
0.7869	Intermediate Similarity	NPC273755
0.7865	Intermediate Similarity	NPC475544
0.7857	Intermediate Similarity	NPC40234
0.7841	Intermediate Similarity	NPC244509
0.7833	Intermediate Similarity	NPC223207
0.7826	Intermediate Similarity	NPC26108
0.7826	Intermediate Similarity	NPC473402
0.7816	Intermediate Similarity	NPC473491
0.7814	Intermediate Similarity	NPC230611
0.7796	Intermediate Similarity	NPC269750
0.7796	Intermediate Similarity	NPC194671
0.7796	Intermediate Similarity	NPC45037
0.779	Intermediate Similarity	NPC471771
0.779	Intermediate Similarity	NPC304074
0.779	Intermediate Similarity	NPC290755
0.7772	Intermediate Similarity	NPC469445
0.775	Intermediate Similarity	NPC220060
0.774	Intermediate Similarity	NPC473580
0.773	Intermediate Similarity	NPC155506
0.773	Intermediate Similarity	NPC476227
0.773	Intermediate Similarity	NPC136797
0.773	Intermediate Similarity	NPC159767
0.7717	Intermediate Similarity	NPC89831
0.7716	Intermediate Similarity	NPC469443
0.7711	Intermediate Similarity	NPC469444
0.7696	Intermediate Similarity	NPC96275
0.7676	Intermediate Similarity	NPC248670
0.7654	Intermediate Similarity	NPC324850
0.7644	Intermediate Similarity	NPC478007
0.7644	Intermediate Similarity	NPC16188
0.764	Intermediate Similarity	NPC476268
0.7634	Intermediate Similarity	NPC279871
0.7627	Intermediate Similarity	NPC261934
0.7627	Intermediate Similarity	NPC5194
0.7617	Intermediate Similarity	NPC51047
0.7571	Intermediate Similarity	NPC478008
0.7558	Intermediate Similarity	NPC476989
0.754	Intermediate Similarity	NPC158277
0.754	Intermediate Similarity	NPC473354
0.7526	Intermediate Similarity	NPC476321
0.75	Intermediate Similarity	NPC214988
0.7487	Intermediate Similarity	NPC471526
0.7474	Intermediate Similarity	NPC246591
0.7473	Intermediate Similarity	NPC114806
0.7472	Intermediate Similarity	NPC300443
0.7462	Intermediate Similarity	NPC80514
0.7459	Intermediate Similarity	NPC63040
0.7459	Intermediate Similarity	NPC141957
0.7455	Intermediate Similarity	NPC477635
0.7455	Intermediate Similarity	NPC477630
0.745	Intermediate Similarity	NPC473450
0.7446	Intermediate Similarity	NPC472923
0.7443	Intermediate Similarity	NPC311658
0.7418	Intermediate Similarity	NPC62104
0.7418	Intermediate Similarity	NPC24617
0.7418	Intermediate Similarity	NPC1390
0.7414	Intermediate Similarity	NPC77905
0.7409	Intermediate Similarity	NPC299806
0.7405	Intermediate Similarity	NPC15068
0.7399	Intermediate Similarity	NPC48202
0.7398	Intermediate Similarity	NPC470728
0.7374	Intermediate Similarity	NPC233702
0.7358	Intermediate Similarity	NPC471050
0.7358	Intermediate Similarity	NPC471048
0.7358	Intermediate Similarity	NPC471049
0.7358	Intermediate Similarity	NPC294951
0.7356	Intermediate Similarity	NPC25539
0.7354	Intermediate Similarity	NPC477462
0.7351	Intermediate Similarity	NPC5719
0.7351	Intermediate Similarity	NPC210377
0.7351	Intermediate Similarity	NPC217804
0.7351	Intermediate Similarity	NPC22883
0.7347	Intermediate Similarity	NPC163961
0.7347	Intermediate Similarity	NPC473305
0.7317	Intermediate Similarity	NPC219350
0.7317	Intermediate Similarity	NPC194699
0.7314	Intermediate Similarity	NPC168861
0.7306	Intermediate Similarity	NPC167763
0.7306	Intermediate Similarity	NPC470903
0.7306	Intermediate Similarity	NPC470112
0.7273	Intermediate Similarity	NPC209463
0.7267	Intermediate Similarity	NPC267237
0.726	Intermediate Similarity	NPC469442
0.726	Intermediate Similarity	NPC277306
0.7238	Intermediate Similarity	NPC473341
0.7236	Intermediate Similarity	NPC65714
0.7236	Intermediate Similarity	NPC328763
0.7234	Intermediate Similarity	NPC66490
0.7234	Intermediate Similarity	NPC473000
0.7222	Intermediate Similarity	NPC473378
0.7222	Intermediate Similarity	NPC473407
0.7222	Intermediate Similarity	NPC7817
0.7222	Intermediate Similarity	NPC475168
0.7219	Intermediate Similarity	NPC254700
0.7216	Intermediate Similarity	NPC91953
0.72	Intermediate Similarity	NPC184933
0.72	Intermediate Similarity	NPC59827
0.7198	Intermediate Similarity	NPC470902
0.7191	Intermediate Similarity	NPC81026
0.7168	Intermediate Similarity	NPC141050
0.7164	Intermediate Similarity	NPC473371
0.7159	Intermediate Similarity	NPC197921
0.7157	Intermediate Similarity	NPC4910
0.7151	Intermediate Similarity	NPC326966
0.715	Intermediate Similarity	NPC475421
0.7143	Intermediate Similarity	NPC122590
0.7136	Intermediate Similarity	NPC248822
0.7135	Intermediate Similarity	NPC315266
0.7135	Intermediate Similarity	NPC266741
0.7129	Intermediate Similarity	NPC471592
0.7119	Intermediate Similarity	NPC469360
0.7104	Intermediate Similarity	NPC39431
0.7094	Intermediate Similarity	NPC323662
0.7094	Intermediate Similarity	NPC477527
0.7079	Intermediate Similarity	NPC476978
0.7071	Intermediate Similarity	NPC329731
0.7059	Intermediate Similarity	NPC328924
0.7045	Intermediate Similarity	NPC313694
0.7045	Intermediate Similarity	NPC242159
0.7032	Intermediate Similarity	NPC323244
0.7019	Intermediate Similarity	NPC246303
0.7011	Intermediate Similarity	NPC287401
0.7005	Intermediate Similarity	NPC469901
0.7	Intermediate Similarity	NPC314358
0.6983	Remote Similarity	NPC326241
0.6978	Remote Similarity	NPC2501
0.6971	Remote Similarity	NPC81845
0.6967	Remote Similarity	NPC295795
0.6965	Remote Similarity	NPC477526
0.6964	Remote Similarity	NPC477633
0.6963	Remote Similarity	NPC186617
0.6949	Remote Similarity	NPC132636
0.6944	Remote Similarity	NPC316008
0.6944	Remote Similarity	NPC313867
0.6927	Remote Similarity	NPC473693
0.6927	Remote Similarity	NPC471568
0.6915	Remote Similarity	NPC471527
0.6914	Remote Similarity	NPC477634
0.6907	Remote Similarity	NPC317362
0.6907	Remote Similarity	NPC318930
0.6898	Remote Similarity	NPC297145
0.6898	Remote Similarity	NPC197743
0.6897	Remote Similarity	NPC130309
0.6897	Remote Similarity	NPC314083
0.6893	Remote Similarity	NPC64205

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 NPC477632 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	129
0.1-0.2	400
0.2-0.3	728
0.3-0.4	2014
0.4-0.5	3931
0.5-0.6	1726
0.6-0.7	209
0.7-0.8	12
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
0.84	Intermediate Similarity	NPD8303	Discontinued
0.7955	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7523	Phase 3
0.7709	Intermediate Similarity	NPD8019	Approved
0.7709	Intermediate Similarity	NPD7495	Discontinued
0.7473	Intermediate Similarity	NPD4652	Approved
0.7414	Intermediate Similarity	NPD7978	Discontinued
0.7374	Intermediate Similarity	NPD7303	Discontinued
0.7347	Intermediate Similarity	NPD7617	Discontinued
0.7314	Intermediate Similarity	NPD8076	Discontinued
0.7263	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD2098	Approved
0.72	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2097	Approved
0.7093	Intermediate Similarity	NPD3136	Phase 2
0.7088	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD5137	Approved
0.7045	Intermediate Similarity	NPD6901	Phase 3
0.7033	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD8292	Phase 2
0.6923	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7484	Phase 3
0.6875	Remote Similarity	NPD7485	Phase 3
0.6875	Remote Similarity	NPD2890	Approved
0.6875	Remote Similarity	NPD2889	Approved
0.6875	Remote Similarity	NPD2017	Approved
0.6875	Remote Similarity	NPD2888	Approved
0.6833	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6255	Approved
0.6827	Remote Similarity	NPD6256	Approved
0.6827	Remote Similarity	NPD6254	Approved
0.6811	Remote Similarity	NPD7613	Discontinued
0.6804	Remote Similarity	NPD6796	Discontinued
0.6798	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6253	Approved
0.6778	Remote Similarity	NPD7450	Phase 2
0.6729	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6188	Approved
0.6713	Remote Similarity	NPD6189	Approved
0.6704	Remote Similarity	NPD8173	Phase 2
0.6704	Remote Similarity	NPD8172	Phase 2
0.6667	Remote Similarity	NPD7608	Discontinued
0.6667	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6187	Approved
0.6667	Remote Similarity	NPD1330	Phase 2
0.6649	Remote Similarity	NPD4566	Approved
0.6649	Remote Similarity	NPD4567	Approved
0.6616	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD2568	Approved
0.6596	Remote Similarity	NPD7131	Phase 3
0.6592	Remote Similarity	NPD5323	Approved
0.659	Remote Similarity	NPD2561	Approved
0.659	Remote Similarity	NPD2562	Approved
0.6575	Remote Similarity	NPD3554	Approved
0.6575	Remote Similarity	NPD3552	Approved
0.6575	Remote Similarity	NPD3553	Approved
0.6575	Remote Similarity	NPD3555	Approved
0.6573	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7811	Phase 3
0.6571	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7810	Phase 3
0.6557	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD8162	Phase 2
0.6552	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6557	Phase 2
0.6546	Remote Similarity	NPD8031	Discontinued
0.6546	Remote Similarity	NPD5219	Approved
0.6546	Remote Similarity	NPD5218	Approved
0.6538	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD3659	Discontinued
0.65	Remote Similarity	NPD8416	Discontinued
0.6486	Remote Similarity	NPD5265	Approved
0.6486	Remote Similarity	NPD5264	Approved
0.6484	Remote Similarity	NPD4126	Approved
0.648	Remote Similarity	NPD5299	Approved
0.648	Remote Similarity	NPD7133	Discontinued
0.6479	Remote Similarity	NPD6863	Phase 2
0.6477	Remote Similarity	NPD4557	Approved
0.6473	Remote Similarity	NPD5077	Approved
0.6473	Remote Similarity	NPD5076	Approved
0.6468	Remote Similarity	NPD5484	Approved
0.6468	Remote Similarity	NPD5485	Approved
0.6464	Remote Similarity	NPD8643	Discontinued
0.6462	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD4125	Approved
0.6452	Remote Similarity	NPD3400	Discontinued
0.6438	Remote Similarity	NPD3879	Approved
0.6436	Remote Similarity	NPD5613	Approved
0.6436	Remote Similarity	NPD5614	Approved
0.6436	Remote Similarity	NPD3988	Approved
0.6436	Remote Similarity	NPD3987	Approved
0.6432	Remote Similarity	NPD8124	Phase 3
0.6432	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5314	Approved
0.6425	Remote Similarity	NPD5356	Approved
0.6425	Remote Similarity	NPD5355	Approved
0.6422	Remote Similarity	NPD7280	Phase 3
0.6422	Remote Similarity	NPD7281	Phase 3
0.642	Remote Similarity	NPD5367	Discontinued
0.642	Remote Similarity	NPD3125	Approved
0.6398	Remote Similarity	NPD7282	Approved
0.6394	Remote Similarity	NPD6505	Approved
0.6394	Remote Similarity	NPD6504	Approved
0.6393	Remote Similarity	NPD3878	Approved
0.639	Remote Similarity	NPD6851	Approved
0.639	Remote Similarity	NPD6853	Approved
0.6378	Remote Similarity	NPD2088	Approved
0.6378	Remote Similarity	NPD2087	Approved
0.6377	Remote Similarity	NPD4435	Approved
0.6373	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD6390	Discontinued
0.6364	Remote Similarity	NPD8255	Phase 2
0.6359	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6297	Approved
0.635	Remote Similarity	NPD7965	Phase 2
0.635	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7451	Discontinued
0.6344	Remote Similarity	NPD6681	Discovery
0.6339	Remote Similarity	NPD6073	Approved
0.6333	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD2517	Approved
0.6329	Remote Similarity	NPD4434	Approved
0.6324	Remote Similarity	NPD2852	Approved
0.6324	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD3061	Approved
0.6319	Remote Similarity	NPD3059	Approved
0.6319	Remote Similarity	NPD6346	Approved
0.6319	Remote Similarity	NPD3062	Approved
0.6316	Remote Similarity	NPD3536	Discontinued
0.6311	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.631	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6852	Discontinued
0.6298	Remote Similarity	NPD5852	Approved
0.6298	Remote Similarity	NPD5851	Approved
0.629	Remote Similarity	NPD7827	Phase 1
0.6289	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6303	Approved
0.6281	Remote Similarity	NPD6304	Approved
0.6281	Remote Similarity	NPD2516	Approved
0.6278	Remote Similarity	NPD5263	Approved
0.6277	Remote Similarity	NPD6676	Phase 2
0.6273	Remote Similarity	NPD2853	Approved
0.6271	Remote Similarity	NPD4659	Approved
0.6264	Remote Similarity	NPD6407	Approved
0.6264	Remote Similarity	NPD6405	Approved
0.6257	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3919	Approved
0.625	Remote Similarity	NPD5725	Approved
0.625	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD8323	Discontinued
0.6243	Remote Similarity	NPD16	Approved
0.6243	Remote Similarity	NPD856	Approved
0.6243	Remote Similarity	NPD318	Approved
0.6243	Remote Similarity	NPD317	Approved
0.623	Remote Similarity	NPD6419	Discontinued
0.623	Remote Similarity	NPD4153	Approved
0.6224	Remote Similarity	NPD5773	Approved
0.6224	Remote Similarity	NPD5772	Approved
0.6222	Remote Similarity	NPD4177	Approved
0.6222	Remote Similarity	NPD4175	Approved
0.6222	Remote Similarity	NPD3040	Approved
0.622	Remote Similarity	NPD4157	Discontinued
0.6218	Remote Similarity	NPD4646	Approved
0.6218	Remote Similarity	NPD4648	Approved
0.6218	Remote Similarity	NPD4647	Approved
0.6218	Remote Similarity	NPD7836	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD3071	Approved
0.6215	Remote Similarity	NPD3073	Approved
0.6215	Remote Similarity	NPD3072	Approved
0.621	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD601	Approved
0.6209	Remote Similarity	NPD598	Approved
0.6209	Remote Similarity	NPD597	Approved
0.6203	Remote Similarity	NPD2022	Approved
0.6201	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD4103	Phase 2
0.6198	Remote Similarity	NPD5229	Approved
0.6198	Remote Similarity	NPD5230	Approved
0.6196	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD6646	Discontinued
0.6193	Remote Similarity	NPD7737	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