NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	714.29
Volume:	708.344
LogP:	3.274
LogD:	2.047
LogS:	-4.591
# Rotatable Bonds:	18
TPSA:	187.26
# H-Bond Aceptor:	14
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.189
Synthetic Accessibility Score:	6.349
Fsp3:	0.568
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.189
MDCK Permeability:	7.579899829579517e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.338
Human Intestinal Absorption (HIA):	0.426
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.799
Plasma Protein Binding (PPB):	58.409637451171875%
Volume Distribution (VD):	1.194
Pgp-substrate:	15.683828353881836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.041
CYP2C19-inhibitor:	0.239
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.487
CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.461
CYP2D6-substrate:	0.02
CYP3A4-inhibitor:	0.856
CYP3A4-substrate:	0.545

ADMET: Excretion

Clearance (CL):	3.978
Half-life (T1/2):	0.675

ADMET: Toxicity

hERG Blockers:	0.073
Human Hepatotoxicity (H-HT):	0.767
Drug-inuced Liver Injury (DILI):	0.904
AMES Toxicity:	0.881
Rat Oral Acute Toxicity:	0.221
Maximum Recommended Daily Dose:	0.816
Skin Sensitization:	0.88
Carcinogencity:	0.454
Eye Corrosion:	0.133
Eye Irritation:	0.152
Respiratory Toxicity:	0.709

Download Data

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

Natural Product: NPC476977

Natural Product ID:	NPC476977
*Common Name:**	[(1S,2S,5S,6S,7S,9R,12R)-12-acetyloxy-5-(2-acetyloxyacetyl)oxy-6-(acetyloxymethyl)-2-hydroxy-2,10-dimethyl-7-[(E)-3-phenylprop-2-enoyl]oxy-11-oxatricyclo[7.2.1.01,6]dodecan-10-yl]methyl (E)-2-methylbut-2-enoate
IUPAC Name:	[(1S,2S,5S,6S,7S,9R,12R)-12-acetyloxy-5-(2-acetyloxyacetyl)oxy-6-(acetyloxymethyl)-2-hydroxy-2,10-dimethyl-7-[(E)-3-phenylprop-2-enoyl]oxy-11-oxatricyclo[7.2.1.01,6]dodecan-10-yl]methyl (E)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	VMQUIDZZSIFSPK-SLCWSKOMSA-N
Standard InCHI:	InChI=1S/C37H46O14/c1-8-22(2)33(43)47-20-34(6)27-18-29(50-30(41)15-14-26-12-10-9-11-13-26)36(21-46-24(4)39)28(49-31(42)19-45-23(3)38)16-17-35(7,44)37(36,51-34)32(27)48-25(5)40/h8-15,27-29,32,44H,16-21H2,1-7H3/b15-14+,22-8+/t27-,28+,29+,32-,34?,35+,36+,37+/m1/s1
SMILES:	C/C=C(\C)/C(=O)OCC1([C@@H]2C[C@@H]([C@@]3([C@H](CC[C@]([C@]3([C@@H]2OC(=O)C)O1)(C)O)OC(=O)COC(=O)C)COC(=O)C)OC(=O)/C=C/C4=CC=CC=C4)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118726323
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002967] Hexacarboxylic acids and derivatives

*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
NPO33650	Denhamia celastroides	Species	Celastraceae	Eukaryota	leave	Walton Bridge Reserve, The Gap, Australia	2012-OCT	PMID[25579619]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	10000	nM	PMID[25579619]

☑ 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 NPC476977 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	241
0.1-0.2	983
0.2-0.3	2169
0.3-0.4	4899
0.4-0.5	8771
0.5-0.6	17558
0.6-0.7	7033
0.7-0.8	777
0.8-0.85	128
0.85-0.9	106
0.9-0.95	15
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC476976
0.9593	High Similarity	NPC476970
0.9516	High Similarity	NPC476972
0.9516	High Similarity	NPC476971
0.9435	High Similarity	NPC475933
0.9435	High Similarity	NPC470158
0.9355	High Similarity	NPC473083
0.9268	High Similarity	NPC473889
0.9268	High Similarity	NPC70973
0.9194	High Similarity	NPC473870
0.9194	High Similarity	NPC473871
0.9187	High Similarity	NPC37641
0.9187	High Similarity	NPC311175
0.9127	High Similarity	NPC473110
0.9127	High Similarity	NPC473082
0.9127	High Similarity	NPC473111
0.9048	High Similarity	NPC114927
0.8971	High Similarity	NPC80895
0.8971	High Similarity	NPC471912
0.8943	High Similarity	NPC473860
0.8905	High Similarity	NPC301946
0.8905	High Similarity	NPC277053
0.8889	High Similarity	NPC16912
0.8862	High Similarity	NPC84129
0.8849	High Similarity	NPC476975
0.8815	High Similarity	NPC97667
0.8815	High Similarity	NPC171207
0.8786	High Similarity	NPC473214
0.8786	High Similarity	NPC470245
0.8769	High Similarity	NPC93632
0.875	High Similarity	NPC41481
0.875	High Similarity	NPC97947
0.875	High Similarity	NPC472576
0.875	High Similarity	NPC27377
0.875	High Similarity	NPC87448
0.875	High Similarity	NPC118080
0.875	High Similarity	NPC291599
0.875	High Similarity	NPC471758
0.8723	High Similarity	NPC51602
0.8714	High Similarity	NPC473215
0.8696	High Similarity	NPC11685
0.8696	High Similarity	NPC95265
0.8696	High Similarity	NPC57628
0.8696	High Similarity	NPC476974
0.8696	High Similarity	NPC95810
0.8696	High Similarity	NPC472570
0.8696	High Similarity	NPC25768
0.8696	High Similarity	NPC472569
0.8696	High Similarity	NPC472573
0.8696	High Similarity	NPC70716
0.8696	High Similarity	NPC188865
0.8696	High Similarity	NPC125106
0.8696	High Similarity	NPC163719
0.8686	High Similarity	NPC472546
0.8682	High Similarity	NPC45821
0.8676	High Similarity	NPC100913
0.8676	High Similarity	NPC90614
0.8676	High Similarity	NPC275592
0.8633	High Similarity	NPC472568
0.8633	High Similarity	NPC472575
0.8633	High Similarity	NPC471104
0.8633	High Similarity	NPC473088
0.8633	High Similarity	NPC158663
0.8633	High Similarity	NPC184817
0.8633	High Similarity	NPC171525
0.8633	High Similarity	NPC174982
0.8633	High Similarity	NPC472572
0.8633	High Similarity	NPC470159
0.8633	High Similarity	NPC70403
0.8633	High Similarity	NPC470157
0.8633	High Similarity	NPC29704
0.8633	High Similarity	NPC96903
0.8633	High Similarity	NPC472571
0.8633	High Similarity	NPC200471
0.8633	High Similarity	NPC177940
0.8633	High Similarity	NPC476973
0.8633	High Similarity	NPC469349
0.8618	High Similarity	NPC473869
0.8605	High Similarity	NPC284022
0.8594	High Similarity	NPC12016
0.8592	High Similarity	NPC470153
0.8592	High Similarity	NPC471103
0.8583	High Similarity	NPC473439
0.8583	High Similarity	NPC300827
0.8571	High Similarity	NPC474935
0.8561	High Similarity	NPC475759
0.8561	High Similarity	NPC475122
0.8561	High Similarity	NPC470231
0.8561	High Similarity	NPC241951
0.8561	High Similarity	NPC470152
0.855	High Similarity	NPC58061
0.8542	High Similarity	NPC282239
0.8527	High Similarity	NPC472373
0.8519	High Similarity	NPC291638
0.8519	High Similarity	NPC66761
0.8519	High Similarity	NPC472577
0.8519	High Similarity	NPC17877
0.8519	High Similarity	NPC195647
0.8511	High Similarity	NPC281717
0.8489	Intermediate Similarity	NPC163087
0.8483	Intermediate Similarity	NPC106895
0.8451	Intermediate Similarity	NPC301556
0.8451	Intermediate Similarity	NPC266265
0.8451	Intermediate Similarity	NPC270590
0.8451	Intermediate Similarity	NPC92293
0.8451	Intermediate Similarity	NPC471101
0.8444	Intermediate Similarity	NPC474608
0.8433	Intermediate Similarity	NPC80599
0.8425	Intermediate Similarity	NPC472393
0.8417	Intermediate Similarity	NPC473755
0.8417	Intermediate Similarity	NPC34012
0.8417	Intermediate Similarity	NPC475513
0.8414	Intermediate Similarity	NPC21410
0.8414	Intermediate Similarity	NPC473670
0.8409	Intermediate Similarity	NPC230331
0.8406	Intermediate Similarity	NPC473109
0.8406	Intermediate Similarity	NPC473081
0.8406	Intermediate Similarity	NPC211137
0.8406	Intermediate Similarity	NPC4341
0.8406	Intermediate Similarity	NPC200592
0.8406	Intermediate Similarity	NPC476094
0.8406	Intermediate Similarity	NPC43241
0.8406	Intermediate Similarity	NPC473613
0.8406	Intermediate Similarity	NPC473758
0.8406	Intermediate Similarity	NPC473060
0.8406	Intermediate Similarity	NPC473112
0.8406	Intermediate Similarity	NPC473085
0.8406	Intermediate Similarity	NPC48017
0.8406	Intermediate Similarity	NPC184747
0.8406	Intermediate Similarity	NPC147880
0.8406	Intermediate Similarity	NPC472547
0.8372	Intermediate Similarity	NPC475328
0.8372	Intermediate Similarity	NPC473749
0.8369	Intermediate Similarity	NPC127857
0.8369	Intermediate Similarity	NPC471107
0.8369	Intermediate Similarity	NPC471100
0.8369	Intermediate Similarity	NPC472556
0.8367	Intermediate Similarity	NPC471102
0.8356	Intermediate Similarity	NPC217091
0.8346	Intermediate Similarity	NPC89324
0.8345	Intermediate Similarity	NPC224491
0.8333	Intermediate Similarity	NPC210591
0.8333	Intermediate Similarity	NPC475652
0.8333	Intermediate Similarity	NPC214550
0.8321	Intermediate Similarity	NPC472545
0.8321	Intermediate Similarity	NPC472551
0.8299	Intermediate Similarity	NPC477474
0.8299	Intermediate Similarity	NPC477472
0.8299	Intermediate Similarity	NPC477470
0.8296	Intermediate Similarity	NPC209851
0.8288	Intermediate Similarity	NPC472549
0.8288	Intermediate Similarity	NPC473611
0.8286	Intermediate Similarity	NPC182869
0.8284	Intermediate Similarity	NPC473443
0.8271	Intermediate Similarity	NPC195224
0.8264	Intermediate Similarity	NPC7095
0.8264	Intermediate Similarity	NPC254558
0.8264	Intermediate Similarity	NPC112216
0.8261	Intermediate Similarity	NPC39549
0.8261	Intermediate Similarity	NPC283375
0.8261	Intermediate Similarity	NPC183122
0.8261	Intermediate Similarity	NPC184109
0.8243	Intermediate Similarity	NPC477467
0.8227	Intermediate Similarity	NPC473673
0.8227	Intermediate Similarity	NPC246480
0.8227	Intermediate Similarity	NPC475429
0.8227	Intermediate Similarity	NPC270498
0.8227	Intermediate Similarity	NPC139067
0.8227	Intermediate Similarity	NPC147217
0.8227	Intermediate Similarity	NPC177340
0.8227	Intermediate Similarity	NPC191082
0.8222	Intermediate Similarity	NPC472418
0.8219	Intermediate Similarity	NPC69425
0.8209	Intermediate Similarity	NPC225103
0.8207	Intermediate Similarity	NPC306799
0.8207	Intermediate Similarity	NPC101043
0.8195	Intermediate Similarity	NPC171007
0.8195	Intermediate Similarity	NPC190849
0.8194	Intermediate Similarity	NPC60509
0.8194	Intermediate Similarity	NPC81698
0.8194	Intermediate Similarity	NPC250046
0.8194	Intermediate Similarity	NPC474564
0.8189	Intermediate Similarity	NPC470820
0.8182	Intermediate Similarity	NPC209592
0.8182	Intermediate Similarity	NPC48599
0.8182	Intermediate Similarity	NPC240115
0.8182	Intermediate Similarity	NPC473602
0.8169	Intermediate Similarity	NPC38696
0.8169	Intermediate Similarity	NPC51314
0.8169	Intermediate Similarity	NPC67777
0.8169	Intermediate Similarity	NPC34943
0.8169	Intermediate Similarity	NPC471139
0.8163	Intermediate Similarity	NPC469730
0.8163	Intermediate Similarity	NPC26033
0.8163	Intermediate Similarity	NPC132599
0.8163	Intermediate Similarity	NPC228204
0.8163	Intermediate Similarity	NPC473632
0.8156	Intermediate Similarity	NPC140021
0.8151	Intermediate Similarity	NPC472548
0.8151	Intermediate Similarity	NPC477905

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 NPC476977 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	659
0.2-0.3	1450
0.3-0.4	3228
0.4-0.5	2219
0.5-0.6	1136
0.6-0.7	233
0.7-0.8	14
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
0.7842	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD4198	Discontinued
0.75	Intermediate Similarity	NPD7236	Approved
0.7432	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD8407	Phase 2
0.7394	Intermediate Similarity	NPD7961	Discontinued
0.7391	Intermediate Similarity	NPD7799	Discontinued
0.7388	Intermediate Similarity	NPD7741	Discontinued
0.7368	Intermediate Similarity	NPD7239	Suspended
0.7346	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD8368	Discontinued
0.7202	Intermediate Similarity	NPD8434	Phase 2
0.72	Intermediate Similarity	NPD6190	Approved
0.7153	Intermediate Similarity	NPD5125	Phase 3
0.7153	Intermediate Similarity	NPD5126	Approved
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD8435	Approved
0.709	Intermediate Similarity	NPD2629	Approved
0.702	Intermediate Similarity	NPD8166	Discontinued
0.7018	Intermediate Similarity	NPD8361	Approved
0.7018	Intermediate Similarity	NPD8360	Approved
0.7	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD8127	Discontinued
0.694	Remote Similarity	NPD6858	Approved
0.694	Remote Similarity	NPD7094	Approved
0.6937	Remote Similarity	NPD7057	Phase 3
0.6937	Remote Similarity	NPD7058	Phase 2
0.6933	Remote Similarity	NPD5763	Approved
0.6933	Remote Similarity	NPD5762	Approved
0.6899	Remote Similarity	NPD6647	Phase 2
0.6897	Remote Similarity	NPD7095	Approved
0.6875	Remote Similarity	NPD8485	Approved
0.687	Remote Similarity	NPD6685	Approved
0.6842	Remote Similarity	NPD2067	Discontinued
0.6821	Remote Similarity	NPD7266	Discontinued
0.6812	Remote Similarity	NPD7516	Approved
0.676	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5736	Approved
0.675	Remote Similarity	NPD37	Approved
0.6748	Remote Similarity	NPD6234	Discontinued
0.6739	Remote Similarity	NPD7327	Approved
0.6739	Remote Similarity	NPD7328	Approved
0.6728	Remote Similarity	NPD4966	Approved
0.6728	Remote Similarity	NPD4965	Approved
0.6728	Remote Similarity	NPD4967	Phase 2
0.6711	Remote Similarity	NPD6355	Discontinued
0.6705	Remote Similarity	NPD8150	Discontinued
0.669	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD7798	Approved
0.6648	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD4060	Phase 1
0.6642	Remote Similarity	NPD6010	Discontinued
0.6642	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD5765	Approved
0.662	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6912	Phase 3
0.6618	Remote Similarity	NPD969	Suspended
0.6615	Remote Similarity	NPD5344	Discontinued
0.6605	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD8378	Approved
0.6596	Remote Similarity	NPD7503	Approved
0.6596	Remote Similarity	NPD8296	Approved
0.6596	Remote Similarity	NPD8380	Approved
0.6596	Remote Similarity	NPD8335	Approved
0.6596	Remote Similarity	NPD8379	Approved
0.6594	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5909	Discontinued
0.6589	Remote Similarity	NPD7638	Approved
0.6587	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7075	Discontinued
0.6581	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD4628	Phase 3
0.6577	Remote Similarity	NPD6663	Approved
0.6577	Remote Similarity	NPD6233	Phase 2
0.6571	Remote Similarity	NPD7610	Discontinued
0.6568	Remote Similarity	NPD7228	Approved
0.6554	Remote Similarity	NPD7008	Discontinued
0.6544	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5048	Discontinued
0.6538	Remote Similarity	NPD7640	Approved
0.6538	Remote Similarity	NPD7639	Approved
0.6533	Remote Similarity	NPD4140	Approved
0.6525	Remote Similarity	NPD8377	Approved
0.6525	Remote Similarity	NPD8294	Approved
0.6522	Remote Similarity	NPD6599	Discontinued
0.6513	Remote Similarity	NPD7097	Phase 1
0.651	Remote Similarity	NPD6798	Discontinued
0.651	Remote Similarity	NPD3764	Approved
0.6507	Remote Similarity	NPD3094	Phase 2
0.6496	Remote Similarity	NPD8297	Approved
0.6479	Remote Similarity	NPD8033	Approved
0.6475	Remote Similarity	NPD5951	Approved
0.6462	Remote Similarity	NPD4225	Approved
0.6455	Remote Similarity	NPD8462	Phase 1
0.6444	Remote Similarity	NPD6686	Approved
0.6444	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD5844	Phase 1
0.6423	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD6764	Approved
0.6416	Remote Similarity	NPD6765	Approved
0.6416	Remote Similarity	NPD7240	Approved
0.6415	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD6637	Approved
0.6408	Remote Similarity	NPD6319	Approved
0.6403	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7819	Suspended
0.6391	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD5735	Approved
0.6375	Remote Similarity	NPD6273	Approved
0.637	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD7199	Phase 2
0.6364	Remote Similarity	NPD5402	Approved
0.6364	Remote Similarity	NPD3817	Phase 2
0.6357	Remote Similarity	NPD6049	Phase 2
0.6357	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD3092	Approved
0.6345	Remote Similarity	NPD4806	Approved
0.6345	Remote Similarity	NPD4807	Approved
0.6341	Remote Similarity	NPD6801	Discontinued
0.6336	Remote Similarity	NPD5926	Approved
0.6327	Remote Similarity	NPD7736	Approved
0.6325	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD5305	Approved
0.6319	Remote Similarity	NPD5306	Approved
0.6316	Remote Similarity	NPD7473	Discontinued
0.6312	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6674	Discontinued
0.6303	Remote Similarity	NPD8455	Phase 2
0.6301	Remote Similarity	NPD7507	Approved
0.6299	Remote Similarity	NPD7838	Discovery
0.629	Remote Similarity	NPD7497	Discontinued
0.6288	Remote Similarity	NPD2066	Phase 3
0.6284	Remote Similarity	NPD7319	Approved
0.6282	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3751	Discontinued
0.6277	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5124	Phase 1
0.6275	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD6784	Approved
0.6271	Remote Similarity	NPD6785	Approved
0.6266	Remote Similarity	NPD4110	Phase 3
0.6266	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD7458	Discontinued
0.6257	Remote Similarity	NPD8319	Approved
0.6257	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD8320	Phase 1
0.625	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8312	Approved
0.625	Remote Similarity	NPD8313	Approved
0.625	Remote Similarity	NPD6799	Approved
0.625	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8032	Phase 2
0.6237	Remote Similarity	NPD8404	Phase 2
0.6235	Remote Similarity	NPD6232	Discontinued
0.6235	Remote Similarity	NPD5403	Approved
0.6235	Remote Similarity	NPD3787	Discontinued
0.6233	Remote Similarity	NPD7492	Approved
0.6216	Remote Similarity	NPD8651	Approved
0.6214	Remote Similarity	NPD4632	Approved
0.6211	Remote Similarity	NPD5401	Approved
0.6209	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD3620	Phase 2
0.6207	Remote Similarity	NPD3095	Discontinued
0.6207	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD5761	Phase 2
0.6205	Remote Similarity	NPD5760	Phase 2
0.6204	Remote Similarity	NPD6899	Approved
0.6204	Remote Similarity	NPD6881	Approved
0.6203	Remote Similarity	NPD7435	Discontinued
0.62	Remote Similarity	NPD5204	Approved
0.6197	Remote Similarity	NPD7115	Discovery
0.6196	Remote Similarity	NPD7700	Phase 2
0.6196	Remote Similarity	NPD1653	Approved
0.6196	Remote Similarity	NPD7699	Phase 2
0.6194	Remote Similarity	NPD5886	Approved
0.6194	Remote Similarity	NPD41	Approved
0.619	Remote Similarity	NPD6616	Approved
0.6187	Remote Similarity	NPD6650	Approved
0.6187	Remote Similarity	NPD8130	Phase 1
0.6187	Remote Similarity	NPD6649	Approved
0.6184	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD7985	Registered
0.6181	Remote Similarity	NPD6054	Approved
0.6181	Remote Similarity	NPD3091	Approved
0.6178	Remote Similarity	NPD6005	Phase 3
0.6178	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD6004	Phase 3
0.6178	Remote Similarity	NPD6002	Phase 3
0.6171	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD4340	Discontinued
0.6164	Remote Similarity	NPD8328	Phase 3

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