Structure

Physi-Chem Properties

Molecular Weight:  285.14
Volume:  298.468
LogP:  1.221
LogD:  2.085
LogS:  -1.82
# Rotatable Bonds:  3
TPSA:  61.72
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.811
Synthetic Accessibility Score:  2.842
Fsp3:  0.294
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.012
MDCK Permeability:  1.4887655197526328e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.94
Human Intestinal Absorption (HIA):  0.019
20% Bioavailability (F20%):  0.984
30% Bioavailability (F30%):  0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.16
Plasma Protein Binding (PPB):  62.61174011230469%
Volume Distribution (VD):  2.341
Pgp-substrate:  28.795242309570312%

ADMET: Metabolism

CYP1A2-inhibitor:  0.159
CYP1A2-substrate:  0.934
CYP2C19-inhibitor:  0.438
CYP2C19-substrate:  0.764
CYP2C9-inhibitor:  0.055
CYP2C9-substrate:  0.738
CYP2D6-inhibitor:  0.837
CYP2D6-substrate:  0.921
CYP3A4-inhibitor:  0.041
CYP3A4-substrate:  0.811

ADMET: Excretion

Clearance (CL):  13.168
Half-life (T1/2):  0.882

ADMET: Toxicity

hERG Blockers:  0.503
Human Hepatotoxicity (H-HT):  0.434
Drug-inuced Liver Injury (DILI):  0.047
AMES Toxicity:  0.177
Rat Oral Acute Toxicity:  0.807
Maximum Recommended Daily Dose:  0.974
Skin Sensitization:  0.924
Carcinogencity:  0.253
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.872

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

  Natural Product: NPC2295

Natural Product ID:  NPC2295
Common Name*:   (1S)-Norjuziphine
IUPAC Name:   (1S)-1-[(4-hydroxyphenyl)methyl]-7-methoxy-1,2,3,4-tetrahydroisoquinolin-8-ol
Synonyms:   (1S)-Norjuziphine
Standard InCHIKey:  BXWMZVREXWPYKF-AWEZNQCLSA-N
Standard InCHI:  InChI=1S/C17H19NO3/c1-21-15-7-4-12-8-9-18-14(16(12)17(15)20)10-11-2-5-13(19)6-3-11/h2-7,14,18-20H,8-10H2,1H3/t14-/m0/s1
SMILES:  COc1ccc2c(c1O)[C@@H](NCC2)Cc1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL462757
PubChem CID:   15690956
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002566] Isoquinolines and derivatives
        • [CHEMONTID:0000054] Benzylisoquinolines

*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
NPO32610 nectandra salicifolia Species Lauraceae Eukaryota trunk bark lower montane rainforest in Costa Rica n.a. PMID[8786363]

☑ 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

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 4.1 ug.mL-1 PMID[450354]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 3.1 ug.mL-1 PMID[450354]

☑ 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 NPC2295 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC477564
0.9724 High Similarity NPC277669
0.9724 High Similarity NPC76213
0.9586 High Similarity NPC207824
0.9586 High Similarity NPC60538
0.9586 High Similarity NPC103379
0.9586 High Similarity NPC477565
0.9448 High Similarity NPC476151
0.9315 High Similarity NPC321505
0.9315 High Similarity NPC191376
0.9315 High Similarity NPC179825
0.9286 High Similarity NPC35627
0.9286 High Similarity NPC476573
0.9286 High Similarity NPC81247
0.9267 High Similarity NPC127674
0.9267 High Similarity NPC276588
0.9267 High Similarity NPC5238
0.9267 High Similarity NPC39701
0.9267 High Similarity NPC172765
0.9267 High Similarity NPC54379
0.9267 High Similarity NPC184026
0.9267 High Similarity NPC295691
0.9267 High Similarity NPC469817
0.9267 High Similarity NPC189266
0.9267 High Similarity NPC2413
0.9267 High Similarity NPC204828
0.9267 High Similarity NPC278799
0.9267 High Similarity NPC207757
0.9267 High Similarity NPC110416
0.9267 High Similarity NPC249797
0.9267 High Similarity NPC193949
0.9252 High Similarity NPC147390
0.9252 High Similarity NPC246587
0.9252 High Similarity NPC135538
0.9252 High Similarity NPC428
0.9252 High Similarity NPC476571
0.9252 High Similarity NPC24233
0.9241 High Similarity NPC294249
0.9178 High Similarity NPC185838
0.9 High Similarity NPC220858
0.9 High Similarity NPC88249
0.9 High Similarity NPC192768
0.9 High Similarity NPC97221
0.9 High Similarity NPC151895
0.8994 High Similarity NPC477020
0.8994 High Similarity NPC192135
0.8994 High Similarity NPC66341
0.8987 High Similarity NPC477562
0.8987 High Similarity NPC26240
0.8987 High Similarity NPC69712
0.8974 High Similarity NPC121275
0.8974 High Similarity NPC4138
0.8974 High Similarity NPC284183
0.8903 High Similarity NPC27410
0.8903 High Similarity NPC166014
0.8897 High Similarity NPC211468
0.8897 High Similarity NPC219233
0.8897 High Similarity NPC170170
0.8854 High Similarity NPC232514
0.8854 High Similarity NPC276944
0.8854 High Similarity NPC238530
0.8836 High Similarity NPC314682
0.8836 High Similarity NPC323123
0.8831 High Similarity NPC170503
0.8831 High Similarity NPC126519
0.8831 High Similarity NPC203784
0.8828 High Similarity NPC253429
0.8812 High Similarity NPC475215
0.8812 High Similarity NPC108434
0.88 High Similarity NPC106295
0.88 High Similarity NPC210437
0.88 High Similarity NPC16107
0.88 High Similarity NPC476144
0.88 High Similarity NPC51957
0.8797 High Similarity NPC13916
0.8797 High Similarity NPC264850
0.8776 High Similarity NPC328750
0.8776 High Similarity NPC188163
0.8776 High Similarity NPC474915
0.8776 High Similarity NPC213206
0.8773 High Similarity NPC474507
0.8765 High Similarity NPC148709
0.8765 High Similarity NPC476577
0.8765 High Similarity NPC173416
0.8759 High Similarity NPC131204
0.8759 High Similarity NPC301050
0.8758 High Similarity NPC133011
0.8758 High Similarity NPC82285
0.875 High Similarity NPC109925
0.8742 High Similarity NPC7467
0.8734 High Similarity NPC24465
0.8726 High Similarity NPC60186
0.871 High Similarity NPC147091
0.8688 High Similarity NPC83198
0.8688 High Similarity NPC204908
0.8681 High Similarity NPC160692
0.8671 High Similarity NPC324144
0.8654 High Similarity NPC79328
0.8634 High Similarity NPC152212
0.8625 High Similarity NPC117188
0.8625 High Similarity NPC205421
0.8625 High Similarity NPC474931
0.8625 High Similarity NPC158376
0.8625 High Similarity NPC12053
0.8625 High Similarity NPC81218
0.8625 High Similarity NPC145832
0.8625 High Similarity NPC306555
0.8616 High Similarity NPC196447
0.8616 High Similarity NPC306843
0.8616 High Similarity NPC136508
0.8616 High Similarity NPC253043
0.8616 High Similarity NPC212794
0.8616 High Similarity NPC13504
0.8616 High Similarity NPC96603
0.8616 High Similarity NPC78222
0.8616 High Similarity NPC477563
0.8614 High Similarity NPC135772
0.8606 High Similarity NPC312918
0.8606 High Similarity NPC477561
0.8606 High Similarity NPC476574
0.8606 High Similarity NPC155442
0.8599 High Similarity NPC111485
0.8553 High Similarity NPC1229
0.8533 High Similarity NPC136860
0.8533 High Similarity NPC128019
0.8533 High Similarity NPC476567
0.8528 High Similarity NPC232386
0.8528 High Similarity NPC152680
0.8528 High Similarity NPC190783
0.8526 High Similarity NPC187022
0.8526 High Similarity NPC80129
0.8521 High Similarity NPC11296
0.8521 High Similarity NPC175890
0.8521 High Similarity NPC82457
0.8521 High Similarity NPC274661
0.8521 High Similarity NPC48490
0.8506 High Similarity NPC274026
0.8483 Intermediate Similarity NPC33338
0.8483 Intermediate Similarity NPC302171
0.8483 Intermediate Similarity NPC300020
0.8476 Intermediate Similarity NPC477558
0.8476 Intermediate Similarity NPC329969
0.8471 Intermediate Similarity NPC29647
0.8471 Intermediate Similarity NPC60295
0.8471 Intermediate Similarity NPC186063
0.8471 Intermediate Similarity NPC191132
0.8452 Intermediate Similarity NPC81733
0.8452 Intermediate Similarity NPC326316
0.8447 Intermediate Similarity NPC240841
0.8447 Intermediate Similarity NPC42549
0.8447 Intermediate Similarity NPC304659
0.8447 Intermediate Similarity NPC250846
0.8447 Intermediate Similarity NPC317272
0.8447 Intermediate Similarity NPC256012
0.8447 Intermediate Similarity NPC86144
0.8447 Intermediate Similarity NPC268503
0.8428 Intermediate Similarity NPC205167
0.8428 Intermediate Similarity NPC249274
0.8408 Intermediate Similarity NPC216459
0.8408 Intermediate Similarity NPC41178
0.8408 Intermediate Similarity NPC138487
0.8405 Intermediate Similarity NPC118274
0.8405 Intermediate Similarity NPC168753
0.8397 Intermediate Similarity NPC26601
0.8397 Intermediate Similarity NPC37272
0.8395 Intermediate Similarity NPC298979
0.8395 Intermediate Similarity NPC210140
0.8385 Intermediate Similarity NPC209377
0.8377 Intermediate Similarity NPC475959
0.8354 Intermediate Similarity NPC146288
0.8354 Intermediate Similarity NPC239775
0.8354 Intermediate Similarity NPC160931
0.8354 Intermediate Similarity NPC37205
0.8353 Intermediate Similarity NPC186546
0.8353 Intermediate Similarity NPC476576
0.8345 Intermediate Similarity NPC160193
0.8344 Intermediate Similarity NPC470324
0.8333 Intermediate Similarity NPC56887
0.8333 Intermediate Similarity NPC195392
0.8333 Intermediate Similarity NPC223077
0.8333 Intermediate Similarity NPC193853
0.8323 Intermediate Similarity NPC475393
0.8323 Intermediate Similarity NPC32154
0.8323 Intermediate Similarity NPC189470
0.8302 Intermediate Similarity NPC475326
0.8301 Intermediate Similarity NPC130926
0.8282 Intermediate Similarity NPC204947
0.8272 Intermediate Similarity NPC39103
0.8272 Intermediate Similarity NPC134858
0.8272 Intermediate Similarity NPC2770
0.8263 Intermediate Similarity NPC320223
0.8263 Intermediate Similarity NPC114364
0.8253 Intermediate Similarity NPC128560
0.8253 Intermediate Similarity NPC229166
0.8253 Intermediate Similarity NPC199465
0.8239 Intermediate Similarity NPC234392
0.8239 Intermediate Similarity NPC31311
0.8232 Intermediate Similarity NPC66573
0.8225 Intermediate Similarity NPC42663
0.8225 Intermediate Similarity NPC271013

  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 NPC2295 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.88 High Similarity NPD4584 Approved
0.8776 High Similarity NPD4664 Clinical (unspecified phase)
0.8767 High Similarity NPD1632 Clinical (unspecified phase)
0.8684 High Similarity NPD6031 Approved
0.8684 High Similarity NPD6030 Approved
0.8543 High Similarity NPD3845 Phase 1
0.8526 High Similarity NPD7298 Approved
0.8421 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.8344 Intermediate Similarity NPD2898 Approved
0.8333 Intermediate Similarity NPD4010 Discontinued
0.8228 Intermediate Similarity NPD4773 Phase 2
0.8228 Intermediate Similarity NPD4772 Phase 2
0.8225 Intermediate Similarity NPD8054 Approved
0.8225 Intermediate Similarity NPD8053 Approved
0.8224 Intermediate Similarity NPD3060 Approved
0.8217 Intermediate Similarity NPD4017 Approved
0.8194 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.8194 Intermediate Similarity NPD3055 Approved
0.8194 Intermediate Similarity NPD3053 Approved
0.8137 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.8129 Intermediate Similarity NPD2421 Approved
0.8129 Intermediate Similarity NPD2420 Approved
0.8117 Intermediate Similarity NPD5241 Discontinued
0.8105 Intermediate Similarity NPD4162 Approved
0.8098 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD6297 Approved
0.8077 Intermediate Similarity NPD1424 Approved
0.8052 Intermediate Similarity NPD3977 Clinical (unspecified phase)
0.8041 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD2977 Approved
0.8012 Intermediate Similarity NPD2489 Approved
0.8012 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD27 Approved
0.8012 Intermediate Similarity NPD2978 Approved
0.8 Intermediate Similarity NPD5160 Discontinued
0.7987 Intermediate Similarity NPD2674 Phase 3
0.7975 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD3640 Phase 3
0.7975 Intermediate Similarity NPD3641 Approved
0.7975 Intermediate Similarity NPD7831 Phase 2
0.7975 Intermediate Similarity NPD3639 Approved
0.7975 Intermediate Similarity NPD7833 Phase 2
0.7974 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7961 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7961 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7939 Intermediate Similarity NPD6107 Approved
0.7919 Intermediate Similarity NPD5718 Phase 2
0.7914 Intermediate Similarity NPD6788 Approved
0.7907 Intermediate Similarity NPD6851 Approved
0.7907 Intermediate Similarity NPD6853 Approved
0.7892 Intermediate Similarity NPD6071 Discontinued
0.7877 Intermediate Similarity NPD5311 Approved
0.7877 Intermediate Similarity NPD5310 Approved
0.7871 Intermediate Similarity NPD5177 Phase 3
0.7853 Intermediate Similarity NPD2560 Approved
0.7853 Intermediate Similarity NPD2563 Approved
0.7844 Intermediate Similarity NPD2969 Approved
0.7844 Intermediate Similarity NPD2970 Approved
0.7843 Intermediate Similarity NPD2155 Approved
0.7843 Intermediate Similarity NPD2156 Approved
0.7843 Intermediate Similarity NPD2154 Approved
0.7811 Intermediate Similarity NPD8251 Approved
0.7811 Intermediate Similarity NPD8252 Approved
0.7811 Intermediate Similarity NPD8099 Discontinued
0.78 Intermediate Similarity NPD3145 Approved
0.78 Intermediate Similarity NPD3144 Approved
0.7799 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD7598 Phase 2
0.7784 Intermediate Similarity NPD3051 Approved
0.7784 Intermediate Similarity NPD4166 Phase 2
0.7765 Intermediate Similarity NPD4873 Discontinued
0.7765 Intermediate Similarity NPD8156 Discontinued
0.7733 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7712 Intermediate Similarity NPD823 Approved
0.7712 Intermediate Similarity NPD817 Approved
0.7692 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD4666 Phase 3
0.7658 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD2677 Approved
0.764 Intermediate Similarity NPD5976 Discontinued
0.7633 Intermediate Similarity NPD4083 Discontinued
0.7632 Intermediate Similarity NPD4474 Approved
0.7632 Intermediate Similarity NPD3530 Approved
0.7632 Intermediate Similarity NPD4475 Approved
0.7632 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD3531 Approved
0.7632 Intermediate Similarity NPD3532 Approved
0.7605 Intermediate Similarity NPD5709 Phase 3
0.7582 Intermediate Similarity NPD3059 Approved
0.7582 Intermediate Similarity NPD3062 Approved
0.7582 Intermediate Similarity NPD3061 Approved
0.758 Intermediate Similarity NPD7153 Discontinued
0.7571 Intermediate Similarity NPD7906 Approved
0.7566 Intermediate Similarity NPD598 Approved
0.7566 Intermediate Similarity NPD597 Approved
0.7566 Intermediate Similarity NPD601 Approved
0.7548 Intermediate Similarity NPD6895 Approved
0.7548 Intermediate Similarity NPD6896 Approved
0.7544 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7543 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7543 Intermediate Similarity NPD7311 Approved
0.7543 Intermediate Similarity NPD7313 Approved
0.7543 Intermediate Similarity NPD4577 Approved
0.7543 Intermediate Similarity NPD7312 Approved
0.7543 Intermediate Similarity NPD7310 Approved
0.7543 Intermediate Similarity NPD4578 Approved
0.7532 Intermediate Similarity NPD2460 Phase 3
0.7532 Intermediate Similarity NPD2459 Approved
0.7532 Intermediate Similarity NPD2458 Approved
0.7516 Intermediate Similarity NPD1130 Approved
0.7516 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD1132 Approved
0.7516 Intermediate Similarity NPD1136 Approved
0.7515 Intermediate Similarity NPD5720 Discontinued
0.7515 Intermediate Similarity NPD7802 Discontinued
0.7514 Intermediate Similarity NPD7479 Phase 2
0.75 Intermediate Similarity NPD2232 Approved
0.75 Intermediate Similarity NPD1753 Discontinued
0.75 Intermediate Similarity NPD2230 Approved
0.75 Intermediate Similarity NPD2233 Approved
0.75 Intermediate Similarity NPD7309 Approved
0.7484 Intermediate Similarity NPD2989 Phase 2
0.7484 Intermediate Similarity NPD2986 Phase 2
0.7484 Intermediate Similarity NPD3054 Approved
0.7484 Intermediate Similarity NPD5314 Approved
0.7484 Intermediate Similarity NPD3052 Approved
0.7469 Intermediate Similarity NPD6090 Discontinued
0.7468 Intermediate Similarity NPD3597 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD1372 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD3124 Discontinued
0.744 Intermediate Similarity NPD4055 Discovery
0.7439 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD5977 Approved
0.7425 Intermediate Similarity NPD5978 Approved
0.7421 Intermediate Similarity NPD5062 Approved
0.7421 Intermediate Similarity NPD5061 Approved
0.7416 Intermediate Similarity NPD4663 Approved
0.7415 Intermediate Similarity NPD2667 Approved
0.7415 Intermediate Similarity NPD2668 Approved
0.7407 Intermediate Similarity NPD2874 Phase 2
0.7407 Intermediate Similarity NPD3645 Discontinued
0.7401 Intermediate Similarity NPD6618 Phase 2
0.7399 Intermediate Similarity NPD5708 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD3122 Phase 3
0.7389 Intermediate Similarity NPD2488 Approved
0.7389 Intermediate Similarity NPD2490 Approved
0.7375 Intermediate Similarity NPD6748 Discontinued
0.7372 Intermediate Similarity NPD2653 Approved
0.7365 Intermediate Similarity NPD4585 Approved
0.7365 Intermediate Similarity NPD2688 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD593 Approved
0.7361 Intermediate Similarity NPD595 Approved
0.736 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD4256 Phase 2
0.7358 Intermediate Similarity NPD4257 Approved
0.7356 Intermediate Similarity NPD6042 Phase 2
0.7356 Intermediate Similarity NPD42 Phase 2
0.7355 Intermediate Similarity NPD3110 Approved
0.7355 Intermediate Similarity NPD3109 Approved
0.7355 Intermediate Similarity NPD2238 Phase 2
0.7346 Intermediate Similarity NPD1774 Approved
0.7342 Intermediate Similarity NPD3156 Discontinued
0.7338 Intermediate Similarity NPD1336 Approved
0.7338 Intermediate Similarity NPD3056 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD824 Approved
0.7329 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD3692 Discontinued
0.7322 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD4727 Phase 1
0.7312 Intermediate Similarity NPD4236 Phase 3
0.7312 Intermediate Similarity NPD4237 Approved
0.7303 Intermediate Similarity NPD9619 Approved
0.7303 Intermediate Similarity NPD9621 Approved
0.7303 Intermediate Similarity NPD9620 Approved
0.7301 Intermediate Similarity NPD3536 Discontinued
0.7301 Intermediate Similarity NPD1771 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD3936 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD9634 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD2120 Phase 2
0.7283 Intermediate Similarity NPD4481 Phase 3
0.7279 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD3687 Approved
0.7273 Intermediate Similarity NPD3686 Approved
0.7267 Intermediate Similarity NPD6331 Phase 2
0.7267 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD5313 Approved
0.7257 Intermediate Similarity NPD5312 Approved
0.7256 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD52 Approved
0.7256 Intermediate Similarity NPD7526 Approved
0.7255 Intermediate Similarity NPD3636 Approved
0.7255 Intermediate Similarity NPD3637 Approved
0.7255 Intermediate Similarity NPD3635 Approved
0.7246 Intermediate Similarity NPD7110 Phase 1
0.7246 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD6087 Phase 1

  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