Structure

Physi-Chem Properties

Molecular Weight:  407.21
Volume:  431.796
LogP:  5.542
LogD:  3.781
LogS:  -5.449
# Rotatable Bonds:  3
TPSA:  62.16
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.626
Synthetic Accessibility Score:  3.604
Fsp3:  0.36
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.047
MDCK Permeability:  1.487319514126284e-05
Pgp-inhibitor:  0.969
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.02
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.843

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.032
Plasma Protein Binding (PPB):  96.79093170166016%
Volume Distribution (VD):  0.635
Pgp-substrate:  2.765671491622925%

ADMET: Metabolism

CYP1A2-inhibitor:  0.755
CYP1A2-substrate:  0.968
CYP2C19-inhibitor:  0.39
CYP2C19-substrate:  0.766
CYP2C9-inhibitor:  0.238
CYP2C9-substrate:  0.841
CYP2D6-inhibitor:  0.465
CYP2D6-substrate:  0.913
CYP3A4-inhibitor:  0.154
CYP3A4-substrate:  0.917

ADMET: Excretion

Clearance (CL):  5.027
Half-life (T1/2):  0.175

ADMET: Toxicity

hERG Blockers:  0.255
Human Hepatotoxicity (H-HT):  0.106
Drug-inuced Liver Injury (DILI):  0.808
AMES Toxicity:  0.561
Rat Oral Acute Toxicity:  0.525
Maximum Recommended Daily Dose:  0.987
Skin Sensitization:  0.539
Carcinogencity:  0.062
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.863

Download Data

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

  Natural Product: NPC119649

Natural Product ID:  NPC119649
Common Name*:   Ancistrolikokine C
IUPAC Name:   (1R,3R)-5-(5-hydroxy-4-methoxy-7-methylnaphthalen-1-yl)-8-methoxy-1,2,3-trimethyl-3,4-dihydro-1H-isoquinolin-6-ol
Synonyms:   Ancistrolikokine C
Standard InCHIKey:  TYMIXIDLUMXISB-HUUCEWRRSA-N
Standard InCHI:  InChI=1S/C25H29NO4/c1-13-9-17-16(7-8-21(29-5)25(17)19(27)10-13)24-18-11-14(2)26(4)15(3)23(18)22(30-6)12-20(24)28/h7-10,12,14-15,27-28H,11H2,1-6H3/t14-,15-/m1/s1
SMILES:  Cc1cc2c(ccc(c2c(c1)O)OC)c1c2C[C@@H](C)N(C)[C@H](C)c2c(cc1O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL487391
PubChem CID:   10024375
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002566] Isoquinolines and derivatives
        • [CHEMONTID:0002195] Naphthylisoquinolines

*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
NPO20256 Ancistrocladus likoko Species Ancistrocladaceae Eukaryota n.a. n.a. n.a. PMID[11076547]
NPO20256 Ancistrocladus likoko Species Ancistrocladaceae Eukaryota n.a. n.a. n.a. Database[TCMID]

☑ 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 = 6.232 ug.mL-1 PMID[539152]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 0.924 ug.mL-1 PMID[539152]

☑ 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 NPC119649 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 NPC230956
1.0 High Similarity NPC271388
1.0 High Similarity NPC205255
1.0 High Similarity NPC235143
0.9933 High Similarity NPC80759
0.9933 High Similarity NPC221864
0.9933 High Similarity NPC79402
0.961 High Similarity NPC193853
0.961 High Similarity NPC56887
0.961 High Similarity NPC223077
0.96 High Similarity NPC123323
0.9545 High Similarity NPC209377
0.9286 High Similarity NPC7393
0.9236 High Similarity NPC195392
0.9221 High Similarity NPC79328
0.9032 High Similarity NPC29647
0.9006 High Similarity NPC239775
0.8944 High Similarity NPC118274
0.8944 High Similarity NPC168753
0.8924 High Similarity NPC60186
0.8909 High Similarity NPC257269
0.8909 High Similarity NPC230276
0.8875 High Similarity NPC264850
0.8875 High Similarity NPC13916
0.8848 High Similarity NPC40496
0.8848 High Similarity NPC119068
0.8812 High Similarity NPC24465
0.875 High Similarity NPC1229
0.875 High Similarity NPC302245
0.875 High Similarity NPC95426
0.875 High Similarity NPC16357
0.8735 High Similarity NPC474507
0.8704 High Similarity NPC205421
0.8704 High Similarity NPC145832
0.8704 High Similarity NPC306555
0.8704 High Similarity NPC474931
0.8704 High Similarity NPC12053
0.8704 High Similarity NPC158376
0.8704 High Similarity NPC81218
0.8704 High Similarity NPC117188
0.8698 High Similarity NPC139783
0.8698 High Similarity NPC65312
0.8696 High Similarity NPC477563
0.8696 High Similarity NPC96603
0.8696 High Similarity NPC196447
0.8696 High Similarity NPC136508
0.8696 High Similarity NPC212794
0.8696 High Similarity NPC13504
0.8696 High Similarity NPC253043
0.8696 High Similarity NPC306843
0.8696 High Similarity NPC78222
0.865 High Similarity NPC83198
0.865 High Similarity NPC204908
0.8647 High Similarity NPC22115
0.8647 High Similarity NPC275680
0.8634 High Similarity NPC324144
0.8616 High Similarity NPC206736
0.8616 High Similarity NPC195766
0.8614 High Similarity NPC173416
0.8614 High Similarity NPC148709
0.8614 High Similarity NPC476577
0.8608 High Similarity NPC244112
0.8605 High Similarity NPC476565
0.8547 High Similarity NPC223236
0.8547 High Similarity NPC259350
0.8521 High Similarity NPC258657
0.8521 High Similarity NPC311973
0.8521 High Similarity NPC15414
0.8521 High Similarity NPC49075
0.8521 High Similarity NPC271013
0.8521 High Similarity NPC7715
0.8521 High Similarity NPC328155
0.8521 High Similarity NPC90998
0.8521 High Similarity NPC290005
0.8521 High Similarity NPC181796
0.8521 High Similarity NPC279228
0.8521 High Similarity NPC229373
0.8521 High Similarity NPC54654
0.8521 High Similarity NPC8836
0.8521 High Similarity NPC182052
0.8521 High Similarity NPC239824
0.8521 High Similarity NPC290582
0.8521 High Similarity NPC42663
0.8521 High Similarity NPC223690
0.8521 High Similarity NPC285931
0.8521 High Similarity NPC251735
0.8521 High Similarity NPC217748
0.8521 High Similarity NPC185639
0.8521 High Similarity NPC104196
0.8521 High Similarity NPC222661
0.8509 High Similarity NPC166014
0.8509 High Similarity NPC27410
0.85 High Similarity NPC476572
0.8497 Intermediate Similarity NPC478093
0.8494 Intermediate Similarity NPC152680
0.8494 Intermediate Similarity NPC190783
0.8494 Intermediate Similarity NPC232386
0.8491 Intermediate Similarity NPC325871
0.8491 Intermediate Similarity NPC99659
0.8488 Intermediate Similarity NPC206900
0.8487 Intermediate Similarity NPC470925
0.8481 Intermediate Similarity NPC26601
0.8476 Intermediate Similarity NPC150879
0.8476 Intermediate Similarity NPC204947
0.8471 Intermediate Similarity NPC167116
0.8471 Intermediate Similarity NPC274716
0.8471 Intermediate Similarity NPC254441
0.8462 Intermediate Similarity NPC286119
0.8448 Intermediate Similarity NPC473589
0.8448 Intermediate Similarity NPC478092
0.8448 Intermediate Similarity NPC30182
0.8448 Intermediate Similarity NPC256124
0.8448 Intermediate Similarity NPC478091
0.8438 Intermediate Similarity NPC186063
0.8434 Intermediate Similarity NPC149090
0.8434 Intermediate Similarity NPC19520
0.8412 Intermediate Similarity NPC30779
0.8397 Intermediate Similarity NPC476151
0.8383 Intermediate Similarity NPC66341
0.8383 Intermediate Similarity NPC192135
0.8383 Intermediate Similarity NPC477020
0.8382 Intermediate Similarity NPC82763
0.8375 Intermediate Similarity NPC189266
0.8375 Intermediate Similarity NPC2413
0.8375 Intermediate Similarity NPC204828
0.8375 Intermediate Similarity NPC207757
0.8375 Intermediate Similarity NPC249797
0.8375 Intermediate Similarity NPC295691
0.8375 Intermediate Similarity NPC184026
0.8375 Intermediate Similarity NPC127674
0.8375 Intermediate Similarity NPC276588
0.8375 Intermediate Similarity NPC278799
0.8375 Intermediate Similarity NPC193949
0.8375 Intermediate Similarity NPC469817
0.8375 Intermediate Similarity NPC5238
0.8375 Intermediate Similarity NPC110416
0.8375 Intermediate Similarity NPC39701
0.8375 Intermediate Similarity NPC172765
0.8375 Intermediate Similarity NPC54379
0.8373 Intermediate Similarity NPC477562
0.8373 Intermediate Similarity NPC69712
0.8373 Intermediate Similarity NPC26240
0.8372 Intermediate Similarity NPC57036
0.8372 Intermediate Similarity NPC214116
0.8372 Intermediate Similarity NPC116465
0.8372 Intermediate Similarity NPC212237
0.8354 Intermediate Similarity NPC134858
0.8354 Intermediate Similarity NPC276665
0.8354 Intermediate Similarity NPC169743
0.8354 Intermediate Similarity NPC265473
0.8343 Intermediate Similarity NPC320223
0.8343 Intermediate Similarity NPC114364
0.8333 Intermediate Similarity NPC229166
0.8333 Intermediate Similarity NPC199465
0.8333 Intermediate Similarity NPC128560
0.8324 Intermediate Similarity NPC186546
0.8324 Intermediate Similarity NPC476576
0.8323 Intermediate Similarity NPC227060
0.8323 Intermediate Similarity NPC317439
0.8323 Intermediate Similarity NPC76682
0.8323 Intermediate Similarity NPC10908
0.8323 Intermediate Similarity NPC198498
0.8323 Intermediate Similarity NPC317145
0.8323 Intermediate Similarity NPC276890
0.8323 Intermediate Similarity NPC63646
0.8323 Intermediate Similarity NPC115284
0.8302 Intermediate Similarity NPC81733
0.8302 Intermediate Similarity NPC326316
0.8293 Intermediate Similarity NPC233650
0.8291 Intermediate Similarity NPC92541
0.8291 Intermediate Similarity NPC477565
0.8291 Intermediate Similarity NPC103379
0.8291 Intermediate Similarity NPC219162
0.8284 Intermediate Similarity NPC241704
0.8276 Intermediate Similarity NPC274661
0.8276 Intermediate Similarity NPC48490
0.8276 Intermediate Similarity NPC82457
0.8276 Intermediate Similarity NPC11296
0.8276 Intermediate Similarity NPC175890
0.8274 Intermediate Similarity NPC12424
0.8274 Intermediate Similarity NPC251580
0.8274 Intermediate Similarity NPC129518
0.8274 Intermediate Similarity NPC41376
0.8269 Intermediate Similarity NPC185838
0.8256 Intermediate Similarity NPC302275
0.8253 Intermediate Similarity NPC298979
0.8253 Intermediate Similarity NPC210140
0.8249 Intermediate Similarity NPC234318
0.8229 Intermediate Similarity NPC60295
0.8229 Intermediate Similarity NPC191132
0.8228 Intermediate Similarity NPC428
0.8228 Intermediate Similarity NPC135538
0.8228 Intermediate Similarity NPC130941
0.8228 Intermediate Similarity NPC24233
0.8228 Intermediate Similarity NPC147390
0.8228 Intermediate Similarity NPC476571
0.8228 Intermediate Similarity NPC246587
0.82 Intermediate Similarity NPC282508
0.8193 Intermediate Similarity NPC81247
0.8193 Intermediate Similarity NPC24264

  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 NPC119649 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
0.8848 High Similarity NPD8453 Clinical (unspecified phase)
0.8521 High Similarity NPD8053 Approved
0.8521 High Similarity NPD8054 Approved
0.8323 Intermediate Similarity NPD8099 Discontinued
0.8323 Intermediate Similarity NPD8252 Approved
0.8323 Intermediate Similarity NPD8251 Approved
0.8274 Intermediate Similarity NPD8156 Discontinued
0.8221 Intermediate Similarity NPD6788 Approved
0.8165 Intermediate Similarity NPD4584 Approved
0.8101 Intermediate Similarity NPD2420 Approved
0.8101 Intermediate Similarity NPD2421 Approved
0.805 Intermediate Similarity NPD7447 Phase 1
0.8013 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD7212 Phase 2
0.7987 Intermediate Similarity NPD7213 Phase 3
0.7879 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7843 Intermediate Similarity NPD4475 Approved
0.7843 Intermediate Similarity NPD4474 Approved
0.7778 Intermediate Similarity NPD6090 Discontinued
0.7712 Intermediate Similarity NPD4625 Phase 3
0.7702 Intermediate Similarity NPD3845 Phase 1
0.7677 Intermediate Similarity NPD2238 Phase 2
0.7677 Intermediate Similarity NPD3109 Approved
0.7677 Intermediate Similarity NPD3110 Approved
0.7662 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD3051 Approved
0.7654 Intermediate Similarity NPD7598 Phase 2
0.7654 Intermediate Similarity NPD7906 Approved
0.7643 Intermediate Similarity NPD7718 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD4055 Discovery
0.7616 Intermediate Similarity NPD2969 Approved
0.7616 Intermediate Similarity NPD2970 Approved
0.76 Intermediate Similarity NPD7479 Phase 2
0.7572 Intermediate Similarity NPD2898 Approved
0.7572 Intermediate Similarity NPD2489 Approved
0.7572 Intermediate Similarity NPD27 Approved
0.7558 Intermediate Similarity NPD6747 Phase 1
0.7548 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD3124 Discontinued
0.7532 Intermediate Similarity NPD4908 Phase 1
0.7531 Intermediate Similarity NPD5241 Discontinued
0.7531 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.753 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD7833 Phase 2
0.7529 Intermediate Similarity NPD7831 Phase 2
0.7528 Intermediate Similarity NPD4578 Approved
0.7528 Intermediate Similarity NPD4577 Approved
0.75 Intermediate Similarity NPD4663 Approved
0.75 Intermediate Similarity NPD1424 Approved
0.7485 Intermediate Similarity NPD7400 Phase 3
0.7485 Intermediate Similarity NPD6667 Approved
0.7485 Intermediate Similarity NPD6666 Approved
0.7484 Intermediate Similarity NPD5155 Approved
0.7484 Intermediate Similarity NPD1753 Discontinued
0.7484 Intermediate Similarity NPD5156 Approved
0.7473 Intermediate Similarity NPD8095 Phase 1
0.7473 Intermediate Similarity NPD6656 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD6748 Discontinued
0.7469 Intermediate Similarity NPD7466 Approved
0.7457 Intermediate Similarity NPD4010 Discontinued
0.7457 Intermediate Similarity NPD6071 Discontinued
0.7453 Intermediate Similarity NPD7037 Approved
0.7443 Intermediate Similarity NPD42 Phase 2
0.7443 Intermediate Similarity NPD6042 Phase 2
0.744 Intermediate Similarity NPD4773 Phase 2
0.744 Intermediate Similarity NPD4772 Phase 2
0.743 Intermediate Similarity NPD7311 Approved
0.743 Intermediate Similarity NPD7312 Approved
0.743 Intermediate Similarity NPD7310 Approved
0.743 Intermediate Similarity NPD7313 Approved
0.7425 Intermediate Similarity NPD4017 Approved
0.7425 Intermediate Similarity NPD4005 Discontinued
0.7421 Intermediate Similarity NPD2200 Suspended
0.7419 Intermediate Similarity NPD3595 Approved
0.7419 Intermediate Similarity NPD2606 Approved
0.7419 Intermediate Similarity NPD2605 Approved
0.7419 Intermediate Similarity NPD3594 Approved
0.7412 Intermediate Similarity NPD2560 Approved
0.7412 Intermediate Similarity NPD2563 Approved
0.7396 Intermediate Similarity NPD7298 Approved
0.7389 Intermediate Similarity NPD7309 Approved
0.7386 Intermediate Similarity NPD7493 Clinical (unspecified phase)
0.7384 Intermediate Similarity NPD5709 Phase 3
0.7378 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD7124 Phase 2
0.7368 Intermediate Similarity NPD2230 Approved
0.7368 Intermediate Similarity NPD2232 Approved
0.7368 Intermediate Similarity NPD2233 Approved
0.736 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD3635 Approved
0.7355 Intermediate Similarity NPD3636 Approved
0.7355 Intermediate Similarity NPD3637 Approved
0.7353 Intermediate Similarity NPD7046 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD6746 Phase 2
0.7341 Intermediate Similarity NPD4666 Phase 3
0.7333 Intermediate Similarity NPD4093 Discontinued
0.732 Intermediate Similarity NPD1669 Approved
0.7312 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD1914 Approved
0.7305 Intermediate Similarity NPD7427 Discontinued
0.7288 Intermediate Similarity NPD7177 Discontinued
0.7288 Intermediate Similarity NPD5940 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD2668 Approved
0.7285 Intermediate Similarity NPD2667 Approved
0.7284 Intermediate Similarity NPD4725 Approved
0.7284 Intermediate Similarity NPD4726 Approved
0.7284 Intermediate Similarity NPD4721 Approved
0.7278 Intermediate Similarity NPD7549 Discontinued
0.7278 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD4481 Phase 3
0.7273 Intermediate Similarity NPD6607 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD5303 Approved
0.7267 Intermediate Similarity NPD5304 Approved
0.7267 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD2568 Approved
0.7247 Intermediate Similarity NPD6020 Phase 2
0.7235 Intermediate Similarity NPD6072 Discontinued
0.7235 Intermediate Similarity NPD7438 Suspended
0.7226 Intermediate Similarity NPD4103 Phase 2
0.7226 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD8051 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD3692 Discontinued
0.7202 Intermediate Similarity NPD3639 Approved
0.7202 Intermediate Similarity NPD3641 Approved
0.7202 Intermediate Similarity NPD6030 Approved
0.7202 Intermediate Similarity NPD6031 Approved
0.7202 Intermediate Similarity NPD3640 Phase 3
0.7195 Intermediate Similarity NPD5177 Phase 3
0.7186 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD6584 Phase 3
0.7178 Intermediate Similarity NPD7030 Discontinued
0.7176 Intermediate Similarity NPD4678 Approved
0.7176 Intermediate Similarity NPD4675 Approved
0.7161 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD3977 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD5754 Discontinued
0.7143 Intermediate Similarity NPD4097 Suspended
0.7143 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD4257 Approved
0.7134 Intermediate Similarity NPD4256 Phase 2
0.712 Intermediate Similarity NPD3452 Approved
0.712 Intermediate Similarity NPD3450 Approved
0.712 Intermediate Similarity NPD2493 Approved
0.712 Intermediate Similarity NPD2494 Approved
0.7108 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD5718 Phase 2
0.7107 Intermediate Similarity NPD7294 Phase 1
0.7104 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD7802 Discontinued
0.7101 Intermediate Similarity NPD4727 Phase 1
0.7097 Intermediate Similarity NPD4749 Approved
0.7097 Intermediate Similarity NPD2488 Approved
0.7097 Intermediate Similarity NPD2490 Approved
0.7097 Intermediate Similarity NPD4659 Approved
0.7091 Intermediate Similarity NPD3060 Approved
0.709 Intermediate Similarity NPD2973 Approved
0.709 Intermediate Similarity NPD2975 Approved
0.709 Intermediate Similarity NPD6284 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD2974 Approved
0.7083 Intermediate Similarity NPD7019 Approved
0.7083 Intermediate Similarity NPD5006 Approved
0.7083 Intermediate Similarity NPD5005 Approved
0.7083 Intermediate Similarity NPD7020 Approved
0.7078 Intermediate Similarity NPD1610 Phase 2
0.7063 Intermediate Similarity NPD7477 Discontinued
0.7059 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD4108 Discontinued
0.7052 Intermediate Similarity NPD4585 Approved
0.7045 Intermediate Similarity NPD5677 Discontinued
0.7044 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD5938 Phase 3
0.7035 Intermediate Similarity NPD5089 Approved
0.7035 Intermediate Similarity NPD5090 Approved
0.7029 Intermediate Similarity NPD8005 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD7837 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD3837 Clinical (unspecified phase)
0.701 Intermediate Similarity NPD4583 Approved
0.701 Intermediate Similarity NPD4582 Approved
0.7006 Intermediate Similarity NPD4098 Discontinued
0.7006 Intermediate Similarity NPD5160 Discontinued
0.7 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.6988 Remote Similarity NPD4236 Phase 3
0.6988 Remote Similarity NPD4237 Approved
0.6987 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6987 Remote Similarity NPD6582 Phase 2
0.6987 Remote Similarity NPD6583 Phase 3
0.6982 Remote Similarity NPD3157 Approved
0.6982 Remote Similarity NPD3158 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