NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	3209.44
Volume:	3073.31
LogP:	-0.437
LogD:	4.042
LogS:	0.473
# Rotatable Bonds:	36
TPSA:	1299.07
# H-Bond Aceptor:	77
# H-Bond Donor:	46
# Rings:	8
# Heavy Atoms:	83

MedChem Properties

QED Drug-Likeness Score:	0.013
Synthetic Accessibility Score:	9.959
Fsp3:	0.657
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:	3.807
MDCK Permeability:	0.052286737
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):	28.08%
Volume Distribution (VD):	-2.047
Pgp-substrate:	70.24%

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):	-4.78
Half-life (T1/2):	0.459

ADMET: Toxicity

hERG Blockers:	0
Human Hepatotoxicity (H-HT):	1
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0
Rat Oral Acute Toxicity:	0
Maximum Recommended Daily Dose:	0
Skin Sensitization:	0.834
Carcinogencity:	0.016
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.908

Download Data

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

Natural Product: NPC477636

Natural Product ID:	NPC477636
*Common Name:**	Cycloviolin A
IUPAC Name:	(1R,7S,12S,15R,18S,21S,24S,30S,33R,36S,39S,42S,45S,48S,54R,57S,60R,63S,66S,69S,72S,75S,78S,81S,84S,90S,93S,99S)-63,69-bis(4-aminobutyl)-66,84-bis(2-amino-2-oxoethyl)-21-benzyl-24,36,48,93-tetrakis[(2S)-butan-2-yl]-81-(3-carbamimidamidopropyl)-12,39,57-tris(hydroxymethyl)-78-[(4-hydroxyphenyl)methyl]-42,45-dimethyl-a,2,5,10,13,16,19,22,25,31,34,37,40,43,46,49,52,55,58,61,64,67,70,73,76,79,82,85,88,91,94-hentriacontaoxo-18,72,90-tri(propan-2-yl)-3a,4a,7a,8a,11a,12a-hexathia-1a,3,6,11,14,17,20,23,26,32,35,38,41,44,47,50,53,56,59,62,65,68,71,74,77,80,83,86,89,92,95-hentriacontazahexacyclo[52.47.4.415,60.433,75.026,30.095,99]tridecahectane-7-carboxylic acid
Synonyms:	Cycloviolin A
Standard InCHIKey:	WVDDKBIDSUUCLT-AWZLLTDASA-N
Standard InCHI:	InChI=1S/C137H216N38O39S6/c1-17-68(11)105-129(206)147-54-100(184)152-89-60-216-215-59-88-112(189)146-53-99(183)150-80(136(213)214)42-43-98(182)151-85(56-176)120(197)163-92-63-219-217-61-90(162-121(198)87(58-178)160-122(89)199)123(200)155-77(33-24-26-44-138)113(190)158-84(52-97(141)181)117(194)153-78(34-25-27-45-139)115(192)168-104(67(9)10)131(208)166-91(124(201)156-81(50-75-38-40-76(179)41-39-75)116(193)154-79(35-28-46-144-137(142)143)114(191)157-83(51-96(140)180)111(188)145-55-101(185)167-102(65(5)6)132(209)173-108(71(14)20-4)135(212)175-48-29-36-94(175)127(204)164-88)62-218-220-64-93(126(203)171-106(69(12)18-2)133(210)161-86(57-177)119(196)149-72(15)109(186)148-73(16)110(187)170-105)165-128(205)95-37-30-47-174(95)134(211)107(70(13)19-3)172-118(195)82(49-74-31-22-21-23-32-74)159-130(207)103(66(7)8)169-125(92)202/h21-23,31-32,38-41,65-73,77-95,102-108,176-179H,17-20,24-30,33-37,42-64,138-139H2,1-16H3,(H2,140,180)(H2,141,181)(H,145,188)(H,146,189)(H,147,206)(H,148,186)(H,149,196)(H,150,183)(H,151,182)(H,152,184)(H,153,194)(H,154,193)(H,155,200)(H,156,201)(H,157,191)(H,158,190)(H,159,207)(H,160,199)(H,161,210)(H,162,198)(H,163,197)(H,164,204)(H,165,205)(H,166,208)(H,167,185)(H,168,192)(H,169,202)(H,170,187)(H,171,203)(H,172,195)(H,173,209)(H,213,214)(H4,142,143,144)/t68-,69-,70-,71-,72-,73-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91+,92-,93-,94-,95-,102-,103-,104-,105-,106-,107-,108-/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](CCC(=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)N[C@H](C(=O)N7CCC[C@H]7C(=O)N3)[C@@H](C)CC)C(C)C)CC(=O)N)CCCNC(=N)N)CC8=CC=C(C=C8)O)C(C)C)CCCCN)CC(=O)N)CCCCN)NC(=O)[C@@H](NC2=O)CO)CO)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44592645
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	1

Activity Type	# Activity
Organism	1

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]

☑ 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 NPC477636 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	203
0.1-0.2	1214
0.2-0.3	6851
0.3-0.4	11274
0.4-0.5	19067
0.5-0.6	3291
0.6-0.7	498
0.7-0.8	226
0.8-0.85	44
0.85-0.9	10
0.9-0.95	7
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9882	High Similarity	NPC477631
0.9711	High Similarity	NPC477639
0.954	High Similarity	NPC477632
0.954	High Similarity	NPC477638
0.9128	High Similarity	NPC477637
0.8736	High Similarity	NPC329295
0.838	Intermediate Similarity	NPC473404
0.8353	Intermediate Similarity	NPC326349
0.8353	Intermediate Similarity	NPC323336
0.8261	Intermediate Similarity	NPC60516
0.8207	Intermediate Similarity	NPC102959
0.8171	Intermediate Similarity	NPC61004
0.8162	Intermediate Similarity	NPC240130
0.8162	Intermediate Similarity	NPC61332
0.8122	Intermediate Similarity	NPC153554
0.809	Intermediate Similarity	NPC328494
0.8034	Intermediate Similarity	NPC475204
0.8034	Intermediate Similarity	NPC274198
0.8034	Intermediate Similarity	NPC198254
0.8034	Intermediate Similarity	NPC475123
0.8012	Intermediate Similarity	NPC56685
0.8	Intermediate Similarity	NPC471165
0.7978	Intermediate Similarity	NPC129486
0.7978	Intermediate Similarity	NPC280022
0.7969	Intermediate Similarity	NPC477551
0.7958	Intermediate Similarity	NPC477550
0.7958	Intermediate Similarity	NPC477552
0.7957	Intermediate Similarity	NPC94862
0.7944	Intermediate Similarity	NPC475532
0.7937	Intermediate Similarity	NPC302715
0.7933	Intermediate Similarity	NPC276506
0.7933	Intermediate Similarity	NPC46009
0.7907	Intermediate Similarity	NPC262166
0.7901	Intermediate Similarity	NPC165285
0.7901	Intermediate Similarity	NPC17698
0.7869	Intermediate Similarity	NPC97526
0.7869	Intermediate Similarity	NPC119652
0.7857	Intermediate Similarity	NPC196243
0.7816	Intermediate Similarity	NPC244509
0.7797	Intermediate Similarity	NPC241794
0.7784	Intermediate Similarity	NPC244336
0.774	Intermediate Similarity	NPC469243
0.773	Intermediate Similarity	NPC475564
0.773	Intermediate Similarity	NPC170302
0.773	Intermediate Similarity	NPC475409
0.7722	Intermediate Similarity	NPC328649
0.7714	Intermediate Similarity	NPC473580
0.7701	Intermediate Similarity	NPC202198
0.7688	Intermediate Similarity	NPC478005
0.7671	Intermediate Similarity	NPC477630
0.7671	Intermediate Similarity	NPC477635
0.7663	Intermediate Similarity	NPC50016
0.7662	Intermediate Similarity	NPC469445
0.765	Intermediate Similarity	NPC306804
0.765	Intermediate Similarity	NPC137627
0.764	Intermediate Similarity	NPC475544
0.7638	Intermediate Similarity	NPC220060
0.7624	Intermediate Similarity	NPC302597
0.7622	Intermediate Similarity	NPC473546
0.7611	Intermediate Similarity	NPC223207
0.7611	Intermediate Similarity	NPC63931
0.7602	Intermediate Similarity	NPC469443
0.76	Intermediate Similarity	NPC469444
0.76	Intermediate Similarity	NPC261934
0.76	Intermediate Similarity	NPC5194
0.7588	Intermediate Similarity	NPC77905
0.7586	Intermediate Similarity	NPC473491
0.7569	Intermediate Similarity	NPC304074
0.7569	Intermediate Similarity	NPC290755
0.7569	Intermediate Similarity	NPC471771
0.7554	Intermediate Similarity	NPC273755
0.7541	Intermediate Similarity	NPC40234
0.7527	Intermediate Similarity	NPC294516
0.7527	Intermediate Similarity	NPC107938
0.7514	Intermediate Similarity	NPC26108
0.75	Intermediate Similarity	NPC230611
0.7487	Intermediate Similarity	NPC45037
0.7487	Intermediate Similarity	NPC96275
0.7487	Intermediate Similarity	NPC269750
0.7487	Intermediate Similarity	NPC194671
0.743	Intermediate Similarity	NPC324850
0.7419	Intermediate Similarity	NPC473402
0.7419	Intermediate Similarity	NPC476227
0.7419	Intermediate Similarity	NPC136797
0.7416	Intermediate Similarity	NPC476268
0.7414	Intermediate Similarity	NPC311658
0.7414	Intermediate Similarity	NPC16188
0.7409	Intermediate Similarity	NPC51047
0.7405	Intermediate Similarity	NPC89831
0.7368	Intermediate Similarity	NPC48202
0.7368	Intermediate Similarity	NPC478007
0.7366	Intermediate Similarity	NPC248670
0.7345	Intermediate Similarity	NPC300443
0.7337	Intermediate Similarity	NPC63040
0.7337	Intermediate Similarity	NPC473450
0.7326	Intermediate Similarity	NPC476989
0.7326	Intermediate Similarity	NPC473354
0.7326	Intermediate Similarity	NPC159767
0.7326	Intermediate Similarity	NPC279871
0.7326	Intermediate Similarity	NPC155506
0.7322	Intermediate Similarity	NPC472923
0.7316	Intermediate Similarity	NPC476321
0.7299	Intermediate Similarity	NPC478008
0.7293	Intermediate Similarity	NPC1390
0.7293	Intermediate Similarity	NPC62104
0.7283	Intermediate Similarity	NPC15068
0.7268	Intermediate Similarity	NPC246591
0.7267	Intermediate Similarity	NPC214988
0.7259	Intermediate Similarity	NPC80514
0.7253	Intermediate Similarity	NPC114806
0.7246	Intermediate Similarity	NPC25539
0.7243	Intermediate Similarity	NPC141957
0.7234	Intermediate Similarity	NPC158277
0.7228	Intermediate Similarity	NPC210377
0.7228	Intermediate Similarity	NPC22883
0.7228	Intermediate Similarity	NPC5719
0.7228	Intermediate Similarity	NPC217804
0.7206	Intermediate Similarity	NPC194699
0.7206	Intermediate Similarity	NPC219350
0.7204	Intermediate Similarity	NPC66490
0.7202	Intermediate Similarity	NPC299806
0.7198	Intermediate Similarity	NPC24617
0.7194	Intermediate Similarity	NPC470728
0.7188	Intermediate Similarity	NPC471526
0.7151	Intermediate Similarity	NPC209463
0.7151	Intermediate Similarity	NPC233702
0.715	Intermediate Similarity	NPC469442
0.715	Intermediate Similarity	NPC277306
0.7135	Intermediate Similarity	NPC141050
0.7121	Intermediate Similarity	NPC328763
0.7111	Intermediate Similarity	NPC473341
0.7098	Intermediate Similarity	NPC167763
0.7098	Intermediate Similarity	NPC470903
0.7098	Intermediate Similarity	NPC470112
0.7095	Intermediate Similarity	NPC475168
0.7095	Intermediate Similarity	NPC7817
0.7086	Intermediate Similarity	NPC91953
0.7085	Intermediate Similarity	NPC184933
0.7085	Intermediate Similarity	NPC59827
0.7072	Intermediate Similarity	NPC470902
0.7062	Intermediate Similarity	NPC471050
0.7062	Intermediate Similarity	NPC294951
0.7062	Intermediate Similarity	NPC471048
0.7062	Intermediate Similarity	NPC81026
0.7062	Intermediate Similarity	NPC471049
0.7056	Intermediate Similarity	NPC163961
0.7056	Intermediate Similarity	NPC473305
0.7053	Intermediate Similarity	NPC477462
0.7041	Intermediate Similarity	NPC4910
0.7035	Intermediate Similarity	NPC267237
0.7029	Intermediate Similarity	NPC477634
0.7029	Intermediate Similarity	NPC197921
0.7021	Intermediate Similarity	NPC473000
0.702	Intermediate Similarity	NPC248822
0.7011	Intermediate Similarity	NPC242159
0.7011	Intermediate Similarity	NPC313694
0.7006	Intermediate Similarity	NPC266741
0.7006	Intermediate Similarity	NPC315266
0.6989	Remote Similarity	NPC168861
0.6989	Remote Similarity	NPC469360
0.698	Remote Similarity	NPC323662
0.698	Remote Similarity	NPC477527
0.6978	Remote Similarity	NPC39431
0.6966	Remote Similarity	NPC314358
0.6954	Remote Similarity	NPC329731
0.695	Remote Similarity	NPC65714
0.6949	Remote Similarity	NPC326241
0.6949	Remote Similarity	NPC476978
0.6943	Remote Similarity	NPC475421
0.6935	Remote Similarity	NPC473407
0.6935	Remote Similarity	NPC473378
0.6919	Remote Similarity	NPC326966
0.6915	Remote Similarity	NPC254700
0.691	Remote Similarity	NPC313867
0.691	Remote Similarity	NPC316008
0.6908	Remote Similarity	NPC246303
0.6882	Remote Similarity	NPC469901
0.6881	Remote Similarity	NPC473371
0.6879	Remote Similarity	NPC287401
0.686	Remote Similarity	NPC130309
0.6854	Remote Similarity	NPC315283
0.6854	Remote Similarity	NPC314388
0.6851	Remote Similarity	NPC2501
0.685	Remote Similarity	NPC477526
0.6847	Remote Similarity	NPC471592
0.6842	Remote Similarity	NPC315388
0.6831	Remote Similarity	NPC122590
0.6816	Remote Similarity	NPC322878
0.6806	Remote Similarity	NPC471568
0.6806	Remote Similarity	NPC473693
0.6802	Remote Similarity	NPC328924
0.6782	Remote Similarity	NPC314083
0.6779	Remote Similarity	NPC81845
0.6777	Remote Similarity	NPC295795
0.6774	Remote Similarity	NPC297145
0.6774	Remote Similarity	NPC197743
0.6773	Remote Similarity	NPC323244
0.6761	Remote Similarity	NPC64205
0.6754	Remote Similarity	NPC186617
0.6753	Remote Similarity	NPC469900

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 NPC477636 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	131
0.1-0.2	396
0.2-0.3	736
0.3-0.4	1935
0.4-0.5	3974
0.5-0.6	1741
0.6-0.7	219
0.7-0.8	17
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
0.8382	Intermediate Similarity	NPD8303	Discontinued
0.7829	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7523	Phase 3
0.7486	Intermediate Similarity	NPD7495	Discontinued
0.7486	Intermediate Similarity	NPD8019	Approved
0.7446	Intermediate Similarity	NPD4652	Approved
0.7283	Intermediate Similarity	NPD8076	Discontinued
0.7283	Intermediate Similarity	NPD7978	Discontinued
0.7228	Intermediate Similarity	NPD2098	Approved
0.7167	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7303	Discontinued
0.7143	Intermediate Similarity	NPD7617	Discontinued
0.712	Intermediate Similarity	NPD2097	Approved
0.7059	Intermediate Similarity	NPD3136	Phase 2
0.7056	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6901	Phase 3
0.7	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD8292	Phase 2
0.6842	Remote Similarity	NPD2889	Approved
0.6842	Remote Similarity	NPD2017	Approved
0.6842	Remote Similarity	NPD2888	Approved
0.6842	Remote Similarity	NPD2890	Approved
0.6771	Remote Similarity	NPD5137	Approved
0.6761	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD6256	Approved
0.6715	Remote Similarity	NPD6254	Approved
0.6715	Remote Similarity	NPD6255	Approved
0.6703	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6796	Discontinued
0.6686	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6253	Approved
0.662	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD4567	Approved
0.6614	Remote Similarity	NPD4566	Approved
0.6611	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD6189	Approved
0.6605	Remote Similarity	NPD6188	Approved
0.658	Remote Similarity	NPD7484	Phase 3
0.658	Remote Similarity	NPD7485	Phase 3
0.6558	Remote Similarity	NPD6187	Approved
0.6556	Remote Similarity	NPD7450	Phase 2
0.6554	Remote Similarity	NPD5323	Approved
0.6534	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD1330	Phase 2
0.6532	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7613	Discontinued
0.648	Remote Similarity	NPD8173	Phase 2
0.648	Remote Similarity	NPD8172	Phase 2
0.6462	Remote Similarity	NPD7608	Discontinued
0.6461	Remote Similarity	NPD8416	Discontinued
0.6448	Remote Similarity	NPD5265	Approved
0.6448	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD5264	Approved
0.6444	Remote Similarity	NPD4126	Approved
0.6441	Remote Similarity	NPD5299	Approved
0.6436	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD5218	Approved
0.6425	Remote Similarity	NPD5219	Approved
0.642	Remote Similarity	NPD4125	Approved
0.6414	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD3988	Approved
0.6398	Remote Similarity	NPD5614	Approved
0.6398	Remote Similarity	NPD5613	Approved
0.6398	Remote Similarity	NPD3987	Approved
0.6387	Remote Similarity	NPD5355	Approved
0.6387	Remote Similarity	NPD5356	Approved
0.6383	Remote Similarity	NPD7131	Phase 3
0.6379	Remote Similarity	NPD5367	Discontinued
0.6368	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD8162	Phase 2
0.6364	Remote Similarity	NPD7282	Approved
0.6359	Remote Similarity	NPD7133	Discontinued
0.6354	Remote Similarity	NPD4557	Approved
0.634	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD2087	Approved
0.6339	Remote Similarity	NPD2088	Approved
0.6338	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6390	Discontinued
0.633	Remote Similarity	NPD3879	Approved
0.6328	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3659	Discontinued
0.6313	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD8124	Phase 3
0.6304	Remote Similarity	NPD6681	Discovery
0.6303	Remote Similarity	NPD7811	Phase 3
0.6303	Remote Similarity	NPD7810	Phase 3
0.6298	Remote Similarity	NPD2568	Approved
0.6294	Remote Similarity	NPD2517	Approved
0.6292	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD6863	Phase 2
0.6286	Remote Similarity	NPD3125	Approved
0.6284	Remote Similarity	NPD3878	Approved
0.628	Remote Similarity	NPD5076	Approved
0.628	Remote Similarity	NPD5077	Approved
0.6275	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6557	Phase 2
0.6269	Remote Similarity	NPD5484	Approved
0.6269	Remote Similarity	NPD5485	Approved
0.6264	Remote Similarity	NPD2562	Approved
0.6264	Remote Similarity	NPD3553	Approved
0.6264	Remote Similarity	NPD3552	Approved
0.6264	Remote Similarity	NPD2561	Approved
0.6264	Remote Similarity	NPD3554	Approved
0.6264	Remote Similarity	NPD3555	Approved
0.6256	Remote Similarity	NPD8031	Discontinued
0.6244	Remote Similarity	NPD6303	Approved
0.6244	Remote Similarity	NPD2516	Approved
0.6244	Remote Similarity	NPD6304	Approved
0.6243	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD8643	Discontinued
0.6243	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD7965	Phase 2
0.6209	Remote Similarity	NPD5725	Approved
0.6209	Remote Similarity	NPD6073	Approved
0.6202	Remote Similarity	NPD6505	Approved
0.6202	Remote Similarity	NPD6504	Approved
0.6198	Remote Similarity	NPD8255	Phase 2
0.6195	Remote Similarity	NPD6851	Approved
0.6195	Remote Similarity	NPD6853	Approved
0.6188	Remote Similarity	NPD4153	Approved
0.6184	Remote Similarity	NPD4157	Discontinued
0.6184	Remote Similarity	NPD4435	Approved
0.618	Remote Similarity	NPD3040	Approved
0.618	Remote Similarity	NPD4175	Approved
0.618	Remote Similarity	NPD4177	Approved
0.6178	Remote Similarity	NPD4648	Approved
0.6178	Remote Similarity	NPD4647	Approved
0.6178	Remote Similarity	NPD4646	Approved
0.6171	Remote Similarity	NPD3072	Approved
0.6171	Remote Similarity	NPD3071	Approved
0.6171	Remote Similarity	NPD3073	Approved
0.6166	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD2853	Approved
0.6162	Remote Similarity	NPD2022	Approved
0.6158	Remote Similarity	NPD5230	Approved
0.6158	Remote Similarity	NPD6297	Approved
0.6158	Remote Similarity	NPD5229	Approved
0.615	Remote Similarity	NPD3400	Discontinued
0.6146	Remote Similarity	NPD7281	Phase 3
0.6146	Remote Similarity	NPD7280	Phase 3
0.6145	Remote Similarity	NPD5263	Approved
0.6145	Remote Similarity	NPD4676	Approved
0.6138	Remote Similarity	NPD2014	Approved
0.6138	Remote Similarity	NPD2016	Approved
0.6138	Remote Similarity	NPD2013	Approved
0.6135	Remote Similarity	NPD4434	Approved
0.6135	Remote Similarity	NPD3919	Approved
0.6129	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD2852	Approved
0.6124	Remote Similarity	NPD7451	Discontinued
0.6122	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.612	Remote Similarity	NPD5314	Approved
0.6114	Remote Similarity	NPD2891	Approved
0.6114	Remote Similarity	NPD4762	Approved
0.6114	Remote Similarity	NPD4761	Approved
0.6111	Remote Similarity	NPD2046	Approved
0.6111	Remote Similarity	NPD2044	Approved
0.6111	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD2048	Approved
0.6111	Remote Similarity	NPD2043	Approved
0.6111	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD2051	Approved
0.6111	Remote Similarity	NPD2047	Approved
0.6111	Remote Similarity	NPD2045	Approved
0.6111	Remote Similarity	NPD21	Approved
0.6106	Remote Similarity	NPD5851	Approved
0.6106	Remote Similarity	NPD5852	Approved
0.6105	Remote Similarity	NPD6419	Discontinued
0.6105	Remote Similarity	NPD16	Approved
0.6105	Remote Similarity	NPD856	Approved
0.6105	Remote Similarity	NPD317	Approved
0.6105	Remote Similarity	NPD318	Approved
0.6103	Remote Similarity	NPD5773	Approved
0.6103	Remote Similarity	NPD5772	Approved
0.6099	Remote Similarity	NPD6346	Approved
0.6085	Remote Similarity	NPD3509	Approved
0.6085	Remote Similarity	NPD3510	Approved
0.6082	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.608	Remote Similarity	NPD2584	Suspended
0.6077	Remote Similarity	NPD597	Approved
0.6077	Remote Similarity	NPD598	Approved
0.6077	Remote Similarity	NPD6836	Approved
0.6077	Remote Similarity	NPD601	Approved
0.6071	Remote Similarity	NPD7494	Clinical (unspecified phase)

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