NPASS Compound

Structure

NPC213567 OpenBabel07101718312D 36 40 0 0 1 0 0 0 0 0999 V2000 -3.3663 -2.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6214 -4.4948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4143 -2.4143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0632 -1.9724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6468 -4.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2359 -3.7242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1592 -1.4622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8081 -1.0204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2867 -3.4304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8758 -2.8067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 -0.9856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5607 -1.4784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8536 -1.4784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3916 -2.2191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9520 -0.2551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0480 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8561 -0.7653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9012 -2.6598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 -0.9856 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7071 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9856 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7071 -2.5488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8536 -1.4784 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8536 0.4928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6010 0.1867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5411 -1.7423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0226 -2.2191 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7071 -3.5344 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8536 1.4784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2979 0.8837 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1556 -0.9717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1286 0.9772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6625 -3.1366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6490 0.4418 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5665 -1.5954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 17 2 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 10 18 1 0 0 0 0 11 13 2 0 0 0 0 12 14 2 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 27 1 0 0 0 0 15 35 1 0 0 0 0 16 28 1 0 0 0 0 16 36 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 12 1 1 0 0 0 19 20 1 0 0 0 0 19 23 1 0 0 0 0 20 11 1 1 0 0 0 20 24 1 0 0 0 0 21 23 1 0 0 0 0 21 27 1 1 0 0 0 22 28 1 0 0 0 0 22 29 2 0 0 0 0 23 28 1 1 0 0 0 24 27 1 0 0 0 0 24 30 2 0 0 0 0 25 31 2 0 0 0 0 25 35 1 0 0 0 0 26 32 2 0 0 0 0 26 36 1 0 0 0 0 27 33 1 6 0 0 0 28 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.15
Volume:	488.746
LogP:	3.502
LogD:	2.79
LogS:	-4.724
# Rotatable Bonds:	8
TPSA:	127.2
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.593
Synthetic Accessibility Score:	4.899
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.031
MDCK Permeability:	2.297583887411747e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.061
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.868

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.17
Plasma Protein Binding (PPB):	100.41600799560547%
Volume Distribution (VD):	1.511
Pgp-substrate:	0.8305319547653198%

ADMET: Metabolism

CYP1A2-inhibitor:	0.64
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.94
CYP2C19-substrate:	0.09
CYP2C9-inhibitor:	0.943
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.848
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.68
CYP3A4-substrate:	0.463

ADMET: Excretion

Clearance (CL):	3.552
Half-life (T1/2):	0.09

ADMET: Toxicity

hERG Blockers:	0.202
Human Hepatotoxicity (H-HT):	0.119
Drug-inuced Liver Injury (DILI):	0.688
AMES Toxicity:	0.344
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.698
Skin Sensitization:	0.878
Carcinogencity:	0.517
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC213567

Natural Product ID:	NPC213567
*Common Name:**	(+)-Grandifloracin
IUPAC Name:	[(1R,2R,3R,7S,8S,9R)-3-(benzoyloxymethyl)-3,9-dihydroxy-4,10-dioxo-1,2,7,8-tetrahydrotricyclo[6.2.2.0^{2,7}]dodeca-3,9-dien-9-yl]methyl benzoate
Synonyms:	(+)-Grandifloracin
Standard InCHIKey:	XXUFTPBMJHFXJE-MPGPANPZSA-N
Standard InCHI:	InChI=1S/C28H24O8/c29-22-14-12-19-20-11-13-21(23(19)28(22,34)16-36-26(32)18-9-5-2-6-10-18)27(33,24(20)30)15-35-25(31)17-7-3-1-4-8-17/h1-14,19-21,23,33-34H,15-16H2/t19-,20+,21-,23-,27+,28-/m1/s1
SMILES:	c1ccc(cc1)C(=O)OC[C@@]1([C@@H]2C=C[C@@H]([C@H]3C=CC(=O)[C@](COC(=O)c4ccccc4)([C@@H]23)O)C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2063132
PubChem CID:	53362276
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters

*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
NPO32880	uvaria dac	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22676269]
NPO32880	uvaria dac	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23092429]

☑ 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	4
Others	4

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	=	14.5	uM	PMID[473068]
NPT2107	Cell Line	PSN1	Homo sapiens	PC50	=	32.6	uM	PMID[473068]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	PC50	=	17.5	uM	PMID[473068]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	500000.0	nM	PMID[473069]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	109000.0	nM	PMID[473069]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	PC50	=	32.7	uM	PMID[473068]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	500000.0	nM	PMID[473069]
NPT27	Others	Unspecified		IC50	=	123000.0	nM	PMID[473069]

☑ 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 NPC213567 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	336
0.1-0.2	1196
0.2-0.3	2468
0.3-0.4	5452
0.4-0.5	9963
0.5-0.6	10486
0.6-0.7	10362
0.7-0.8	2233
0.8-0.85	161
0.85-0.9	39
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9007	High Similarity	NPC127857
0.8966	High Similarity	NPC242262
0.8966	High Similarity	NPC256142
0.8966	High Similarity	NPC158333
0.8966	High Similarity	NPC237549
0.8966	High Similarity	NPC473414
0.8966	High Similarity	NPC472030
0.8966	High Similarity	NPC1173
0.8966	High Similarity	NPC304876
0.8966	High Similarity	NPC77719
0.8966	High Similarity	NPC472022
0.8966	High Similarity	NPC249471
0.8966	High Similarity	NPC257213
0.8966	High Similarity	NPC472005
0.8966	High Similarity	NPC265395
0.8958	High Similarity	NPC306799
0.8958	High Similarity	NPC101043
0.8951	High Similarity	NPC60509
0.8951	High Similarity	NPC81698
0.8951	High Similarity	NPC250046
0.8904	High Similarity	NPC112523
0.8904	High Similarity	NPC472549
0.8904	High Similarity	NPC114410
0.8904	High Similarity	NPC26033
0.8904	High Similarity	NPC228204
0.8889	High Similarity	NPC198455
0.8889	High Similarity	NPC165260
0.8889	High Similarity	NPC161239
0.8889	High Similarity	NPC7095
0.8889	High Similarity	NPC112216
0.8784	High Similarity	NPC469771
0.8776	High Similarity	NPC282239
0.8767	High Similarity	NPC472548
0.8725	High Similarity	NPC471102
0.8716	High Similarity	NPC217091
0.8716	High Similarity	NPC106895
0.8699	High Similarity	NPC51602
0.8699	High Similarity	NPC471103
0.8658	High Similarity	NPC472393
0.8639	High Similarity	NPC477905
0.8581	High Similarity	NPC11588
0.8581	High Similarity	NPC248265
0.8581	High Similarity	NPC229545
0.8581	High Similarity	NPC134685
0.8581	High Similarity	NPC219419
0.8571	High Similarity	NPC470153
0.8531	High Similarity	NPC182869
0.8523	High Similarity	NPC114357
0.8523	High Similarity	NPC473670
0.8523	High Similarity	NPC21410
0.8523	High Similarity	NPC155329
0.8523	High Similarity	NPC259144
0.8503	High Similarity	NPC473214
0.8503	High Similarity	NPC254558
0.8503	High Similarity	NPC91730
0.8503	High Similarity	NPC470245
0.8483	Intermediate Similarity	NPC471107
0.8483	Intermediate Similarity	NPC471100
0.8462	Intermediate Similarity	NPC224491
0.8446	Intermediate Similarity	NPC197037
0.8435	Intermediate Similarity	NPC476975
0.8435	Intermediate Similarity	NPC473215
0.8425	Intermediate Similarity	NPC477737
0.8425	Intermediate Similarity	NPC474935
0.8414	Intermediate Similarity	NPC472569
0.8414	Intermediate Similarity	NPC472573
0.8414	Intermediate Similarity	NPC475759
0.8414	Intermediate Similarity	NPC11685
0.8414	Intermediate Similarity	NPC163719
0.8414	Intermediate Similarity	NPC470152
0.8414	Intermediate Similarity	NPC70716
0.8414	Intermediate Similarity	NPC95265
0.8414	Intermediate Similarity	NPC125106
0.8414	Intermediate Similarity	NPC57628
0.8414	Intermediate Similarity	NPC472570
0.8414	Intermediate Similarity	NPC241951
0.8414	Intermediate Similarity	NPC25768
0.8414	Intermediate Similarity	NPC95810
0.8414	Intermediate Similarity	NPC188865
0.8414	Intermediate Similarity	NPC476974
0.8411	Intermediate Similarity	NPC469417
0.8403	Intermediate Similarity	NPC472546
0.8392	Intermediate Similarity	NPC171207
0.8392	Intermediate Similarity	NPC97667
0.8392	Intermediate Similarity	NPC472547
0.8377	Intermediate Similarity	NPC66193
0.8369	Intermediate Similarity	NPC477896
0.8369	Intermediate Similarity	NPC477893
0.8367	Intermediate Similarity	NPC281717
0.8367	Intermediate Similarity	NPC217918
0.8356	Intermediate Similarity	NPC174982
0.8356	Intermediate Similarity	NPC470157
0.8356	Intermediate Similarity	NPC171525
0.8356	Intermediate Similarity	NPC177940
0.8356	Intermediate Similarity	NPC184817
0.8356	Intermediate Similarity	NPC200471
0.8356	Intermediate Similarity	NPC472571
0.8356	Intermediate Similarity	NPC96903
0.8356	Intermediate Similarity	NPC472556
0.8356	Intermediate Similarity	NPC469349
0.8356	Intermediate Similarity	NPC476973
0.8356	Intermediate Similarity	NPC158663
0.8356	Intermediate Similarity	NPC29704
0.8356	Intermediate Similarity	NPC470159
0.8356	Intermediate Similarity	NPC473088
0.8356	Intermediate Similarity	NPC472572
0.8356	Intermediate Similarity	NPC70403
0.8356	Intermediate Similarity	NPC472575
0.8356	Intermediate Similarity	NPC472568
0.8356	Intermediate Similarity	NPC471104
0.8345	Intermediate Similarity	NPC163087
0.8345	Intermediate Similarity	NPC477894
0.8333	Intermediate Similarity	NPC27377
0.8333	Intermediate Similarity	NPC87448
0.8333	Intermediate Similarity	NPC97947
0.8333	Intermediate Similarity	NPC291599
0.8333	Intermediate Similarity	NPC41481
0.8333	Intermediate Similarity	NPC16912
0.8333	Intermediate Similarity	NPC472576
0.8333	Intermediate Similarity	NPC77493
0.8333	Intermediate Similarity	NPC118080
0.8323	Intermediate Similarity	NPC471134
0.8322	Intermediate Similarity	NPC472371
0.8322	Intermediate Similarity	NPC472395
0.8312	Intermediate Similarity	NPC55744
0.8311	Intermediate Similarity	NPC266265
0.8311	Intermediate Similarity	NPC301556
0.8311	Intermediate Similarity	NPC471101
0.8311	Intermediate Similarity	NPC270590
0.8311	Intermediate Similarity	NPC92293
0.831	Intermediate Similarity	NPC472551
0.831	Intermediate Similarity	NPC472545
0.831	Intermediate Similarity	NPC472374
0.831	Intermediate Similarity	NPC472372
0.8299	Intermediate Similarity	NPC469513
0.8288	Intermediate Similarity	NPC475122
0.8288	Intermediate Similarity	NPC470231
0.828	Intermediate Similarity	NPC102465
0.8278	Intermediate Similarity	NPC132599
0.8278	Intermediate Similarity	NPC469730
0.8278	Intermediate Similarity	NPC251139
0.8278	Intermediate Similarity	NPC473632
0.8278	Intermediate Similarity	NPC473611
0.8276	Intermediate Similarity	NPC34012
0.8269	Intermediate Similarity	NPC61891
0.8264	Intermediate Similarity	NPC477904
0.8264	Intermediate Similarity	NPC90614
0.8264	Intermediate Similarity	NPC100913
0.8264	Intermediate Similarity	NPC183270
0.8264	Intermediate Similarity	NPC275592
0.8258	Intermediate Similarity	NPC329960
0.8258	Intermediate Similarity	NPC295408
0.8258	Intermediate Similarity	NPC150893
0.8252	Intermediate Similarity	NPC39549
0.8247	Intermediate Similarity	NPC476077
0.8235	Intermediate Similarity	NPC469399
0.8219	Intermediate Similarity	NPC477468
0.8205	Intermediate Similarity	NPC471493
0.8176	Intermediate Similarity	NPC473602
0.817	Intermediate Similarity	NPC477735
0.8169	Intermediate Similarity	NPC48929
0.8169	Intermediate Similarity	NPC329913
0.8169	Intermediate Similarity	NPC126516
0.8165	Intermediate Similarity	NPC40138
0.8163	Intermediate Similarity	NPC80895
0.8163	Intermediate Similarity	NPC471912
0.8163	Intermediate Similarity	NPC38696
0.8156	Intermediate Similarity	NPC472394
0.8156	Intermediate Similarity	NPC209851
0.8146	Intermediate Similarity	NPC327962
0.8141	Intermediate Similarity	NPC322420
0.8138	Intermediate Similarity	NPC4341
0.8138	Intermediate Similarity	NPC43241
0.8138	Intermediate Similarity	NPC473758
0.8138	Intermediate Similarity	NPC48017
0.8138	Intermediate Similarity	NPC476094
0.8138	Intermediate Similarity	NPC473112
0.8138	Intermediate Similarity	NPC473613
0.8138	Intermediate Similarity	NPC473060
0.8138	Intermediate Similarity	NPC200592
0.8138	Intermediate Similarity	NPC147880
0.8138	Intermediate Similarity	NPC211137
0.8138	Intermediate Similarity	NPC184747
0.8138	Intermediate Similarity	NPC473109
0.8138	Intermediate Similarity	NPC473085
0.8138	Intermediate Similarity	NPC473081
0.8133	Intermediate Similarity	NPC469448
0.8125	Intermediate Similarity	NPC183122
0.8125	Intermediate Similarity	NPC283375
0.8117	Intermediate Similarity	NPC477736
0.8116	Intermediate Similarity	NPC470765
0.8113	Intermediate Similarity	NPC477471
0.8113	Intermediate Similarity	NPC477466
0.8113	Intermediate Similarity	NPC477473
0.8113	Intermediate Similarity	NPC477469
0.8112	Intermediate Similarity	NPC66761
0.8112	Intermediate Similarity	NPC291638
0.8112	Intermediate Similarity	NPC17877
0.8112	Intermediate Similarity	NPC472577
0.8112	Intermediate Similarity	NPC195647

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 NPC213567 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	802
0.2-0.3	1438
0.3-0.4	2762
0.4-0.5	2231
0.5-0.6	1199
0.6-0.7	380
0.7-0.8	47
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8108	Intermediate Similarity	NPD7236	Approved
0.7961	Intermediate Similarity	NPD7239	Suspended
0.795	Intermediate Similarity	NPD7799	Discontinued
0.7844	Intermediate Similarity	NPD8150	Discontinued
0.7651	Intermediate Similarity	NPD8368	Discontinued
0.7647	Intermediate Similarity	NPD8361	Approved
0.7647	Intermediate Similarity	NPD8360	Approved
0.7647	Intermediate Similarity	NPD8435	Approved
0.7639	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7058	Phase 2
0.761	Intermediate Similarity	NPD7057	Phase 3
0.7529	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8434	Phase 2
0.7515	Intermediate Similarity	NPD8407	Phase 2
0.7486	Intermediate Similarity	NPD8485	Approved
0.7484	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7075	Discontinued
0.7445	Intermediate Similarity	NPD4198	Discontinued
0.7405	Intermediate Similarity	NPD6599	Discontinued
0.7405	Intermediate Similarity	NPD4380	Phase 2
0.7386	Intermediate Similarity	NPD4628	Phase 3
0.7375	Intermediate Similarity	NPD7819	Suspended
0.7365	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6799	Approved
0.7347	Intermediate Similarity	NPD3764	Approved
0.7342	Intermediate Similarity	NPD7458	Discontinued
0.7342	Intermediate Similarity	NPD3226	Approved
0.7341	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6190	Approved
0.7329	Intermediate Similarity	NPD3817	Phase 2
0.732	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6801	Discontinued
0.7279	Intermediate Similarity	NPD7008	Discontinued
0.7273	Intermediate Similarity	NPD8166	Discontinued
0.7267	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD8312	Approved
0.7251	Intermediate Similarity	NPD8313	Approved
0.725	Intermediate Similarity	NPD7411	Suspended
0.7246	Intermediate Similarity	NPD7473	Discontinued
0.7246	Intermediate Similarity	NPD2629	Approved
0.7222	Intermediate Similarity	NPD5402	Approved
0.7215	Intermediate Similarity	NPD5403	Approved
0.7197	Intermediate Similarity	NPD5401	Approved
0.719	Intermediate Similarity	NPD2346	Discontinued
0.7186	Intermediate Similarity	NPD6166	Phase 2
0.7186	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7961	Discontinued
0.7179	Intermediate Similarity	NPD3300	Phase 2
0.7178	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD6535	Approved
0.7175	Intermediate Similarity	NPD6534	Approved
0.7169	Intermediate Similarity	NPD6232	Discontinued
0.7134	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5406	Approved
0.7124	Intermediate Similarity	NPD5404	Approved
0.7124	Intermediate Similarity	NPD5405	Approved
0.7124	Intermediate Similarity	NPD5408	Approved
0.7122	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD5951	Approved
0.7114	Intermediate Similarity	NPD2313	Discontinued
0.7104	Intermediate Similarity	NPD8319	Approved
0.7104	Intermediate Similarity	NPD8320	Phase 1
0.7101	Intermediate Similarity	NPD3751	Discontinued
0.7089	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2799	Discontinued
0.7059	Intermediate Similarity	NPD5844	Phase 1
0.7059	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2182	Approved
0.7056	Intermediate Similarity	NPD7700	Phase 2
0.7056	Intermediate Similarity	NPD7699	Phase 2
0.7051	Intermediate Similarity	NPD3750	Approved
0.7051	Intermediate Similarity	NPD7003	Approved
0.7049	Intermediate Similarity	NPD7435	Discontinued
0.7029	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1470	Approved
0.7006	Intermediate Similarity	NPD6959	Discontinued
0.6988	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6778	Approved
0.6978	Remote Similarity	NPD6776	Approved
0.6978	Remote Similarity	NPD6779	Approved
0.6978	Remote Similarity	NPD6780	Approved
0.6978	Remote Similarity	NPD6782	Approved
0.6978	Remote Similarity	NPD6781	Approved
0.6978	Remote Similarity	NPD6777	Approved
0.697	Remote Similarity	NPD1238	Approved
0.6966	Remote Similarity	NPD1201	Approved
0.6964	Remote Similarity	NPD3787	Discontinued
0.6957	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1510	Phase 2
0.6948	Remote Similarity	NPD3748	Approved
0.694	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1930	Approved
0.694	Remote Similarity	NPD1929	Approved
0.6937	Remote Similarity	NPD6273	Approved
0.6936	Remote Similarity	NPD6765	Approved
0.6936	Remote Similarity	NPD6764	Approved
0.6928	Remote Similarity	NPD3749	Approved
0.6923	Remote Similarity	NPD9545	Approved
0.6918	Remote Similarity	NPD7390	Discontinued
0.6914	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2935	Discontinued
0.6897	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1934	Approved
0.6889	Remote Similarity	NPD1237	Approved
0.6887	Remote Similarity	NPD6798	Discontinued
0.6879	Remote Similarity	NPD6797	Phase 2
0.6875	Remote Similarity	NPD2534	Approved
0.6875	Remote Similarity	NPD2532	Approved
0.6875	Remote Similarity	NPD2533	Approved
0.6875	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7768	Phase 2
0.6867	Remote Similarity	NPD3882	Suspended
0.6863	Remote Similarity	NPD6355	Discontinued
0.6859	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6287	Discontinued
0.6848	Remote Similarity	NPD8455	Phase 2
0.6846	Remote Similarity	NPD2798	Approved
0.6845	Remote Similarity	NPD5494	Approved
0.6839	Remote Similarity	NPD7251	Discontinued
0.6832	Remote Similarity	NPD1512	Approved
0.6828	Remote Similarity	NPD5126	Approved
0.6828	Remote Similarity	NPD5305	Approved
0.6828	Remote Similarity	NPD5125	Phase 3
0.6828	Remote Similarity	NPD5306	Approved
0.6825	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7874	Approved
0.6821	Remote Similarity	NPD7074	Phase 3
0.6815	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1549	Phase 2
0.6813	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD8127	Discontinued
0.6803	Remote Similarity	NPD4878	Approved
0.6803	Remote Similarity	NPD1608	Approved
0.6802	Remote Similarity	NPD3818	Discontinued
0.68	Remote Similarity	NPD7808	Phase 3
0.6795	Remote Similarity	NPD2796	Approved
0.6792	Remote Similarity	NPD2354	Approved
0.679	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD4136	Approved
0.6781	Remote Similarity	NPD4106	Approved
0.6781	Remote Similarity	NPD4135	Approved
0.6781	Remote Similarity	NPD4879	Approved
0.678	Remote Similarity	NPD6785	Approved
0.678	Remote Similarity	NPD6784	Approved
0.6774	Remote Similarity	NPD7697	Approved
0.6774	Remote Similarity	NPD7696	Phase 3
0.6774	Remote Similarity	NPD7698	Approved
0.677	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD164	Approved
0.6763	Remote Similarity	NPD7054	Approved
0.6753	Remote Similarity	NPD230	Phase 1
0.6752	Remote Similarity	NPD1471	Phase 3
0.6752	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD2801	Approved
0.6747	Remote Similarity	NPD1465	Phase 2
0.6743	Remote Similarity	NPD6559	Discontinued
0.674	Remote Similarity	NPD6212	Phase 3
0.674	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6213	Phase 3
0.6738	Remote Similarity	NPD7871	Phase 2
0.6738	Remote Similarity	NPD7870	Phase 2
0.6735	Remote Similarity	NPD4807	Approved
0.6735	Remote Similarity	NPD4806	Approved
0.6732	Remote Similarity	NPD6233	Phase 2
0.6731	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5049	Phase 3
0.6725	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7472	Approved
0.672	Remote Similarity	NPD7701	Phase 2
0.6716	Remote Similarity	NPD2066	Phase 3
0.6715	Remote Similarity	NPD5048	Discontinued
0.6711	Remote Similarity	NPD7095	Approved
0.671	Remote Similarity	NPD1607	Approved
0.6708	Remote Similarity	NPD1511	Approved
0.6707	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7177	Discontinued
0.6702	Remote Similarity	NPD7801	Approved
0.6702	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4060	Phase 1
0.6688	Remote Similarity	NPD1240	Approved
0.6688	Remote Similarity	NPD1551	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