NPASS Compound

Structure

NPC11445 OpenBabel07101719152D 38 42 0 0 1 0 0 0 0 0999 V2000 0.5296 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1944 3.0995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7290 0.6727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6939 -2.0725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7541 2.3117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6308 -1.1873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0376 -0.2738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9795 1.6793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9711 -1.1942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7339 2.5117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5718 -0.3948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0676 -1.6229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6363 -1.2919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4498 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5875 0.7593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4156 1.5408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8461 0.5998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6944 2.2335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7323 0.5922 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2024 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 -1.1215 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0685 -1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 -2.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0485 -0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0540 -0.3783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4553 0.4307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6680 -0.2375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7121 1.0998 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2806 -0.5542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 21 1 0 0 0 0 4 23 1 0 0 0 0 7 10 1 0 0 0 0 7 12 1 0 0 0 0 8 9 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 13 1 0 0 0 0 11 14 2 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 25 1 0 0 0 0 15 27 2 0 0 0 0 16 29 2 0 0 0 0 17 30 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 28 2 0 0 0 0 20 35 1 0 0 0 0 22 3 1 6 0 0 0 23 26 1 0 0 0 0 24 5 1 1 0 0 0 24 28 1 0 0 0 0 25 34 1 6 0 0 0 26 6 1 6 0 0 0 26 31 1 0 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 29 35 1 0 0 0 0 30 37 2 0 0 0 0 31 32 1 0 0 0 0 31 34 1 6 0 0 0 32 24 1 1 0 0 0 32 36 1 0 0 0 0 33 34 1 0 0 0 0 33 36 2 0 0 0 0 33 38 1 0 0 0 0 34 30 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	510.32
Volume:	567.047
LogP:	7.166
LogD:	5.257
LogS:	-4.492
# Rotatable Bonds:	3
TPSA:	61.96
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.333
Synthetic Accessibility Score:	6.076
Fsp3:	0.471
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-4.862
MDCK Permeability:	1.52934153447859e-05
Pgp-inhibitor:	0.632
Pgp-substrate:	0.984
Human Intestinal Absorption (HIA):	0.063
20% Bioavailability (F20%):	0.256
30% Bioavailability (F30%):	0.12

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094
Plasma Protein Binding (PPB):	99.52713775634766%
Volume Distribution (VD):	3.155
Pgp-substrate:	3.939714193344116%

ADMET: Metabolism

CYP1A2-inhibitor:	0.421
CYP1A2-substrate:	0.278
CYP2C19-inhibitor:	0.963
CYP2C19-substrate:	0.595
CYP2C9-inhibitor:	0.929
CYP2C9-substrate:	0.816
CYP2D6-inhibitor:	0.624
CYP2D6-substrate:	0.751
CYP3A4-inhibitor:	0.97
CYP3A4-substrate:	0.279

ADMET: Excretion

Clearance (CL):	6.028
Half-life (T1/2):	0.11

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.239
Drug-inuced Liver Injury (DILI):	0.101
AMES Toxicity:	0.211
Rat Oral Acute Toxicity:	0.889
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.467
Carcinogencity:	0.231
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC11445

Natural Product ID:	NPC11445
*Common Name:**	MMDCZRJSKCICND-PYZWPHHPSA-N
IUPAC Name:	n.a.
Synonyms:	Chaetoglobosin-510
Standard InCHIKey:	MMDCZRJSKCICND-PYZWPHHPSA-N
Standard InCHI:	InChI=1S/C34H42N2O2/c1-6-26-23(4)19-25-14-11-13-22(3)18-21(2)12-7-10-17-30(37)34(25)31(26)32(36-33(34)38)24(5)28-20-35-29-16-9-8-15-27(28)29/h8-11,14-20,22,24-26,31-32,35H,6-7,12-13H2,1-5H3,(H,36,38)/b14-11+,17-10+,21-18+/t22-,24+,25-,26+,31-,32-,34+/m0/s1
SMILES:	CC[C@@H]1C(=C[C@H]2[C@]3([C@@H]1[C@@H](N=C3O)[C@@H](c1c[nH]c3c1cccc3)C)C(=O)/C=C/CC/C(=C/[C@H](C/C=C/2)C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL473549
PubChem CID:	11627627
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001819] Isoindoles and derivatives [CHEMONTID:0002496] Isoindolines [CHEMONTID:0001820] Isoindolones

*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
NPO33041	phomospis asparagi	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16309305]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT730	Cell Line	MC-38	Mus musculus	Activity	=	150.0	Zone units	PMID[461063]

☑ 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 NPC11445 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	316
0.1-0.2	1921
0.2-0.3	10633
0.3-0.4	21223
0.4-0.5	4107
0.5-0.6	2090
0.6-0.7	1706
0.7-0.8	607
0.8-0.85	71
0.85-0.9	6
0.9-0.95	14
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9942	High Similarity	NPC195239
0.9942	High Similarity	NPC157828
0.9503	High Similarity	NPC98715
0.9402	High Similarity	NPC127677
0.9402	High Similarity	NPC258062
0.9351	High Similarity	NPC271862
0.9348	High Similarity	NPC225821
0.9348	High Similarity	NPC46225
0.9101	High Similarity	NPC151976
0.9101	High Similarity	NPC87856
0.9058	High Similarity	NPC132211
0.9053	High Similarity	NPC267965
0.8958	High Similarity	NPC204491
0.8958	High Similarity	NPC203614
0.8871	High Similarity	NPC300183
0.8757	High Similarity	NPC213468
0.8731	High Similarity	NPC2395
0.8643	High Similarity	NPC266192
0.8641	High Similarity	NPC47190
0.86	High Similarity	NPC235885
0.86	High Similarity	NPC141428
0.8557	High Similarity	NPC267926
0.855	High Similarity	NPC147446
0.8519	High Similarity	NPC252338
0.8515	High Similarity	NPC57690
0.8362	Intermediate Similarity	NPC201700
0.836	Intermediate Similarity	NPC227582
0.8301	Intermediate Similarity	NPC290529
0.8287	Intermediate Similarity	NPC151939
0.8266	Intermediate Similarity	NPC75540
0.8266	Intermediate Similarity	NPC211572
0.8266	Intermediate Similarity	NPC80597
0.8266	Intermediate Similarity	NPC212376
0.8266	Intermediate Similarity	NPC70922
0.8232	Intermediate Similarity	NPC267885
0.8208	Intermediate Similarity	NPC259644
0.8208	Intermediate Similarity	NPC469763
0.8208	Intermediate Similarity	NPC25008
0.8208	Intermediate Similarity	NPC73952
0.8208	Intermediate Similarity	NPC469765
0.8208	Intermediate Similarity	NPC469760
0.8208	Intermediate Similarity	NPC469786
0.8202	Intermediate Similarity	NPC49954
0.8202	Intermediate Similarity	NPC474561
0.8202	Intermediate Similarity	NPC160105
0.8197	Intermediate Similarity	NPC300688
0.8177	Intermediate Similarity	NPC149155
0.8177	Intermediate Similarity	NPC203468
0.8177	Intermediate Similarity	NPC110500
0.8172	Intermediate Similarity	NPC235684
0.8156	Intermediate Similarity	NPC78020
0.8142	Intermediate Similarity	NPC55772
0.8142	Intermediate Similarity	NPC248041
0.8142	Intermediate Similarity	NPC126709
0.8125	Intermediate Similarity	NPC477041
0.8125	Intermediate Similarity	NPC477044
0.8122	Intermediate Similarity	NPC314603
0.8118	Intermediate Similarity	NPC280290
0.8105	Intermediate Similarity	NPC267343
0.809	Intermediate Similarity	NPC311276
0.8085	Intermediate Similarity	NPC321708
0.8075	Intermediate Similarity	NPC94752
0.8075	Intermediate Similarity	NPC99428
0.8068	Intermediate Similarity	NPC469762
0.8065	Intermediate Similarity	NPC228835
0.8051	Intermediate Similarity	NPC260900
0.8048	Intermediate Similarity	NPC70155
0.8043	Intermediate Similarity	NPC283219
0.8042	Intermediate Similarity	NPC154339
0.8034	Intermediate Similarity	NPC282231
0.8031	Intermediate Similarity	NPC131887
0.8011	Intermediate Similarity	NPC469785
0.8	Intermediate Similarity	NPC477042
0.799	Intermediate Similarity	NPC477045
0.799	Intermediate Similarity	NPC74413
0.7989	Intermediate Similarity	NPC194640
0.7989	Intermediate Similarity	NPC14113
0.7989	Intermediate Similarity	NPC145885
0.7989	Intermediate Similarity	NPC213629
0.7989	Intermediate Similarity	NPC84827
0.7989	Intermediate Similarity	NPC111275
0.7978	Intermediate Similarity	NPC279918
0.7959	Intermediate Similarity	NPC476874
0.7959	Intermediate Similarity	NPC476073
0.7956	Intermediate Similarity	NPC63751
0.7941	Intermediate Similarity	NPC473310
0.7908	Intermediate Similarity	NPC475506
0.7892	Intermediate Similarity	NPC284775
0.7889	Intermediate Similarity	NPC40779
0.7885	Intermediate Similarity	NPC476818
0.7879	Intermediate Similarity	NPC477043
0.7869	Intermediate Similarity	NPC6982
0.7868	Intermediate Similarity	NPC155143
0.7861	Intermediate Similarity	NPC314372
0.7849	Intermediate Similarity	NPC11126
0.7846	Intermediate Similarity	NPC171317
0.7846	Intermediate Similarity	NPC473640
0.7842	Intermediate Similarity	NPC278434
0.7842	Intermediate Similarity	NPC17059
0.781	Intermediate Similarity	NPC476491
0.7806	Intermediate Similarity	NPC293917
0.7802	Intermediate Similarity	NPC54988
0.7796	Intermediate Similarity	NPC59269
0.7794	Intermediate Similarity	NPC474412
0.7789	Intermediate Similarity	NPC62749
0.7789	Intermediate Similarity	NPC315555
0.7784	Intermediate Similarity	NPC105818
0.7784	Intermediate Similarity	NPC24678
0.7778	Intermediate Similarity	NPC477003
0.7767	Intermediate Similarity	NPC477714
0.7765	Intermediate Similarity	NPC286427
0.776	Intermediate Similarity	NPC95783
0.7755	Intermediate Similarity	NPC265576
0.7749	Intermediate Similarity	NPC317030
0.7746	Intermediate Similarity	NPC190296
0.7737	Intermediate Similarity	NPC188387
0.7737	Intermediate Similarity	NPC163421
0.7723	Intermediate Similarity	NPC162860
0.7723	Intermediate Similarity	NPC223791
0.7723	Intermediate Similarity	NPC107077
0.7723	Intermediate Similarity	NPC478158
0.7722	Intermediate Similarity	NPC41257
0.772	Intermediate Similarity	NPC117244
0.772	Intermediate Similarity	NPC476460
0.772	Intermediate Similarity	NPC473763
0.7717	Intermediate Similarity	NPC194411
0.7716	Intermediate Similarity	NPC100321
0.7711	Intermediate Similarity	NPC54420
0.7709	Intermediate Similarity	NPC285469
0.7708	Intermediate Similarity	NPC65215
0.7708	Intermediate Similarity	NPC173028
0.7701	Intermediate Similarity	NPC64436
0.7701	Intermediate Similarity	NPC248454
0.77	Intermediate Similarity	NPC473376
0.7692	Intermediate Similarity	NPC202812
0.7688	Intermediate Similarity	NPC469766
0.7688	Intermediate Similarity	NPC293216
0.7684	Intermediate Similarity	NPC165495
0.768	Intermediate Similarity	NPC131718
0.7672	Intermediate Similarity	NPC233936
0.7672	Intermediate Similarity	NPC71037
0.7665	Intermediate Similarity	NPC67288
0.7656	Intermediate Similarity	NPC204565
0.765	Intermediate Similarity	NPC42372
0.7641	Intermediate Similarity	NPC474177
0.7637	Intermediate Similarity	NPC16667
0.7633	Intermediate Similarity	NPC477715
0.763	Intermediate Similarity	NPC469784
0.763	Intermediate Similarity	NPC469783
0.763	Intermediate Similarity	NPC469768
0.763	Intermediate Similarity	NPC469780
0.763	Intermediate Similarity	NPC469767
0.763	Intermediate Similarity	NPC469761
0.763	Intermediate Similarity	NPC469779
0.7629	Intermediate Similarity	NPC138370
0.7624	Intermediate Similarity	NPC230869
0.7622	Intermediate Similarity	NPC280548
0.7614	Intermediate Similarity	NPC229332
0.7614	Intermediate Similarity	NPC262898
0.7606	Intermediate Similarity	NPC68354
0.7604	Intermediate Similarity	NPC474707
0.7602	Intermediate Similarity	NPC133366
0.76	Intermediate Similarity	NPC193761
0.7596	Intermediate Similarity	NPC271797
0.7596	Intermediate Similarity	NPC21174
0.7594	Intermediate Similarity	NPC275305
0.7594	Intermediate Similarity	NPC37423
0.7592	Intermediate Similarity	NPC472294
0.7588	Intermediate Similarity	NPC470497
0.7577	Intermediate Similarity	NPC206967
0.7577	Intermediate Similarity	NPC83111
0.7576	Intermediate Similarity	NPC470499
0.7574	Intermediate Similarity	NPC475288
0.7568	Intermediate Similarity	NPC154293
0.7566	Intermediate Similarity	NPC219336
0.7566	Intermediate Similarity	NPC176199
0.7566	Intermediate Similarity	NPC248462
0.7566	Intermediate Similarity	NPC215795
0.7563	Intermediate Similarity	NPC179701
0.7561	Intermediate Similarity	NPC320968
0.7557	Intermediate Similarity	NPC159856
0.7556	Intermediate Similarity	NPC207726
0.7551	Intermediate Similarity	NPC304203
0.754	Intermediate Similarity	NPC313791
0.7539	Intermediate Similarity	NPC163055
0.7536	Intermediate Similarity	NPC478157
0.7527	Intermediate Similarity	NPC67056
0.7527	Intermediate Similarity	NPC318065
0.7527	Intermediate Similarity	NPC135141
0.7527	Intermediate Similarity	NPC92796
0.7527	Intermediate Similarity	NPC206819
0.7527	Intermediate Similarity	NPC56765
0.7526	Intermediate Similarity	NPC175474
0.7525	Intermediate Similarity	NPC272483
0.7524	Intermediate Similarity	NPC75634
0.7524	Intermediate Similarity	NPC6865
0.7524	Intermediate Similarity	NPC153980
0.7513	Intermediate Similarity	NPC181502
0.7513	Intermediate Similarity	NPC85066
0.7513	Intermediate Similarity	NPC183662

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 NPC11445 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	529
0.2-0.3	726
0.3-0.4	1895
0.4-0.5	2672
0.5-0.6	2176
0.6-0.7	797
0.7-0.8	146
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8407	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD2091	Phase 2
0.8261	Intermediate Similarity	NPD2096	Phase 2
0.8207	Intermediate Similarity	NPD2092	Phase 2
0.8207	Intermediate Similarity	NPD2094	Phase 2
0.8207	Intermediate Similarity	NPD2095	Phase 2
0.8177	Intermediate Similarity	NPD482	Approved
0.8132	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD5426	Phase 3
0.795	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD8431	Approved
0.7923	Intermediate Similarity	NPD750	Phase 2
0.7906	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD2144	Approved
0.7861	Intermediate Similarity	NPD3038	Discontinued
0.7807	Intermediate Similarity	NPD6595	Phase 3
0.7806	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD8094	Discontinued
0.7708	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD6664	Approved
0.77	Intermediate Similarity	NPD5901	Discontinued
0.7696	Intermediate Similarity	NPD8093	Discontinued
0.7692	Intermediate Similarity	NPD7618	Phase 3
0.7692	Intermediate Similarity	NPD7619	Phase 3
0.7673	Intermediate Similarity	NPD2509	Approved
0.7673	Intermediate Similarity	NPD2510	Approved
0.7673	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD7957	Phase 1
0.7662	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD4076	Approved
0.766	Intermediate Similarity	NPD4079	Approved
0.7656	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7621	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD3506	Approved
0.7606	Intermediate Similarity	NPD3505	Approved
0.7604	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD8073	Approved
0.7594	Intermediate Similarity	NPD5065	Approved
0.7584	Intermediate Similarity	NPD2172	Phase 1
0.7572	Intermediate Similarity	NPD786	Approved
0.7563	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD8072	Approved
0.7561	Intermediate Similarity	NPD7470	Discontinued
0.7554	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD4075	Phase 2
0.7538	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD6999	Discontinued
0.7525	Intermediate Similarity	NPD6987	Phase 1
0.7524	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD484	Approved
0.75	Intermediate Similarity	NPD3394	Approved
0.75	Intermediate Similarity	NPD4601	Approved
0.75	Intermediate Similarity	NPD3389	Approved
0.75	Intermediate Similarity	NPD4600	Approved
0.75	Intermediate Similarity	NPD3393	Approved
0.7488	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD1722	Approved
0.7475	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD2844	Phase 3
0.7463	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD8272	Phase 2
0.7435	Intermediate Similarity	NPD5473	Discontinued
0.743	Intermediate Similarity	NPD3100	Discontinued
0.7429	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7187	Phase 2
0.7424	Intermediate Similarity	NPD7944	Discontinued
0.7421	Intermediate Similarity	NPD4181	Approved
0.7407	Intermediate Similarity	NPD7824	Approved
0.7405	Intermediate Similarity	NPD3323	Discontinued
0.7399	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD4499	Approved
0.7385	Intermediate Similarity	NPD3961	Discontinued
0.7382	Intermediate Similarity	NPD8386	Phase 2
0.738	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4703	Approved
0.7374	Intermediate Similarity	NPD4702	Approved
0.7366	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7948	Phase 1
0.7347	Intermediate Similarity	NPD7233	Approved
0.7347	Intermediate Similarity	NPD7234	Approved
0.7344	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7666	Phase 3
0.733	Intermediate Similarity	NPD7665	Phase 2
0.732	Intermediate Similarity	NPD6178	Phase 3
0.732	Intermediate Similarity	NPD7564	Discontinued
0.7317	Intermediate Similarity	NPD7001	Phase 3
0.7316	Intermediate Similarity	NPD4128	Approved
0.7315	Intermediate Similarity	NPD7731	Approved
0.7315	Intermediate Similarity	NPD7730	Approved
0.731	Intermediate Similarity	NPD3871	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3870	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7951	Approved
0.7306	Intermediate Similarity	NPD7790	Approved
0.7306	Intermediate Similarity	NPD7953	Approved
0.7306	Intermediate Similarity	NPD7950	Approved
0.7306	Intermediate Similarity	NPD7791	Approved
0.7306	Intermediate Similarity	NPD7789	Approved
0.7306	Intermediate Similarity	NPD7952	Approved
0.7299	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4462	Approved
0.7293	Intermediate Similarity	NPD4463	Approved
0.7277	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6242	Discontinued
0.7268	Intermediate Similarity	NPD3318	Approved
0.7268	Intermediate Similarity	NPD3320	Approved
0.7268	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD3319	Phase 1
0.7254	Intermediate Similarity	NPD2481	Approved
0.7254	Intermediate Similarity	NPD2479	Phase 3
0.7249	Intermediate Similarity	NPD1325	Approved
0.7249	Intermediate Similarity	NPD1326	Approved
0.7238	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7271	Approved
0.7216	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD3178	Discontinued
0.7211	Intermediate Similarity	NPD3609	Approved
0.7211	Intermediate Similarity	NPD3610	Approved
0.72	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4640	Approved
0.7196	Intermediate Similarity	NPD4639	Approved
0.7196	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD2640	Approved
0.7196	Intermediate Similarity	NPD4638	Approved
0.7196	Intermediate Similarity	NPD2641	Approved
0.7191	Intermediate Similarity	NPD1592	Phase 3
0.7186	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD2336	Approved
0.7184	Intermediate Similarity	NPD56	Approved
0.7184	Intermediate Similarity	NPD8282	Approved
0.7184	Intermediate Similarity	NPD8283	Approved
0.7178	Intermediate Similarity	NPD5003	Discontinued
0.7177	Intermediate Similarity	NPD4051	Discontinued
0.7164	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD4427	Phase 2
0.7156	Intermediate Similarity	NPD6164	Phase 2
0.7156	Intermediate Similarity	NPD6165	Phase 2
0.7151	Intermediate Similarity	NPD3717	Discontinued
0.715	Intermediate Similarity	NPD2008	Discontinued
0.7143	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2639	Approved
0.7143	Intermediate Similarity	NPD2642	Approved
0.7136	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6176	Phase 1
0.7135	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2580	Discontinued
0.7135	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4848	Phase 1
0.7128	Intermediate Similarity	NPD5138	Approved
0.7128	Intermediate Similarity	NPD5140	Approved
0.7123	Intermediate Similarity	NPD7970	Approved
0.7123	Intermediate Similarity	NPD7781	Approved
0.7123	Intermediate Similarity	NPD7780	Approved
0.7123	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1038	Approved
0.7112	Intermediate Similarity	NPD1404	Approved
0.7112	Intermediate Similarity	NPD2511	Approved
0.7112	Intermediate Similarity	NPD1403	Approved
0.7109	Intermediate Similarity	NPD2411	Approved
0.7092	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7191	Phase 2
0.7073	Intermediate Similarity	NPD6479	Discontinued
0.7071	Intermediate Similarity	NPD6217	Discontinued
0.7065	Intermediate Similarity	NPD5505	Discontinued
0.7064	Intermediate Similarity	NPD7269	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD2753	Discontinued
0.7056	Intermediate Similarity	NPD5818	Discontinued
0.705	Intermediate Similarity	NPD2564	Approved
0.705	Intermediate Similarity	NPD2565	Phase 2
0.7044	Intermediate Similarity	NPD2307	Discontinued
0.7037	Intermediate Similarity	NPD3583	Phase 2
0.7035	Intermediate Similarity	NPD4948	Discontinued
0.7032	Intermediate Similarity	NPD7603	Discontinued
0.7032	Intermediate Similarity	NPD7711	Discontinued
0.7031	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD4852	Phase 2
0.7027	Intermediate Similarity	NPD2837	Discontinued
0.7024	Intermediate Similarity	NPD7308	Discontinued
0.7022	Intermediate Similarity	NPD2896	Discontinued
0.7021	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD8114	Approved
0.7019	Intermediate Similarity	NPD8115	Approved
0.7018	Intermediate Similarity	NPD6850	Phase 2

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