NPASS Compound

Structure

NPC471235 OpenBabel07101719142D 36 39 0 0 1 0 0 0 0 0999 V2000 -4.0247 -2.3946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0247 -2.3946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7953 -0.3872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9543 0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5385 -1.0563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6974 0.2308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7953 -0.3872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9543 0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0032 0.5909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0032 0.5909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4895 -0.7473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5385 -1.0563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6974 0.2308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 1.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4895 -0.7473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 4.5388 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 4.5388 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.3305 -2.0345 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 5.6485 0.5398 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.4680 2.2382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 5.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2327 -1.4164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2327 -1.4164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 34 1 0 0 0 0 2 35 1 0 0 0 0 3 5 1 0 0 0 0 3 12 2 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 15 2 0 0 0 0 6 15 1 0 0 0 0 7 12 1 0 0 0 0 7 20 2 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 17 2 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 19 2 0 0 0 0 13 21 1 0 0 0 0 14 23 1 0 0 0 0 15 34 1 0 0 0 0 16 24 2 0 0 0 0 16 27 1 0 0 0 0 17 24 1 0 0 0 0 17 28 1 0 0 0 0 18 25 2 0 0 0 0 18 29 1 0 0 0 0 19 25 1 0 0 0 0 19 30 1 0 0 0 0 20 21 1 0 0 0 0 20 36 1 0 0 0 0 21 22 2 0 0 0 0 22 23 1 0 0 0 0 22 26 1 0 0 0 0 23 31 1 1 0 0 0 24 32 1 0 0 0 0 25 35 1 0 0 0 0 26 33 2 0 0 0 0 26 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	741.78
Volume:	522.265
LogP:	5.883
LogD:	2.946
LogS:	-4.689
# Rotatable Bonds:	6
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.254
Synthetic Accessibility Score:	3.522
Fsp3:	0.115
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.688
MDCK Permeability:	1.6862317352206446e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.582
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.782

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	102.8954086303711%
Volume Distribution (VD):	0.351
Pgp-substrate:	7.887660503387451%

ADMET: Metabolism

CYP1A2-inhibitor:	0.704
CYP1A2-substrate:	0.214
CYP2C19-inhibitor:	0.813
CYP2C19-substrate:	0.166
CYP2C9-inhibitor:	0.872
CYP2C9-substrate:	0.113
CYP2D6-inhibitor:	0.042
CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.236
CYP3A4-substrate:	0.184

ADMET: Excretion

Clearance (CL):	0.809
Half-life (T1/2):	0.058

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.925
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.843
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.586
Carcinogencity:	0.163
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.868

Download Data

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

Natural Product: NPC471235

Natural Product ID:	NPC471235
*Common Name:**	Cadiolide H
IUPAC Name:	(5Z)-4-(3,5-dibromo-4-hydroxyphenyl)-3-[(S)-(3,5-dibromo-4-methoxyphenyl)-hydroxymethyl]-5-[(4-methoxyphenyl)methylidene]furan-2-one
Synonyms:
Standard InCHIKey:	PFYWKGUTCUHXDB-QVARGSHZSA-N
Standard InCHI:	InChI=1S/C26H18Br4O6/c1-34-15-5-3-12(4-6-15)7-20-21(13-8-16(27)24(32)17(28)9-13)22(26(33)36-20)23(31)14-10-18(29)25(35-2)19(30)11-14/h3-11,23,31-32H,1-2H3/b20-7-/t23-/m0/s1
SMILES:	COC1=CC=C(C=C1)C=C2C(=C(C(=O)O2)C(C3=CC(=C(C(=C3)Br)OC)Br)O)C4=CC(=C(C(=C4)Br)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2402008
PubChem CID:	71455774
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO33080	synoicum sp.	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22652254]
NPO33080	synoicum sp.	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23145909]
NPO33080	synoicum sp.	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23747224]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1
MIC	2

Activity Type	# Activity
Individual Protein	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	17160.0	nM	PMID[573433]
NPT1173	Organism	Candida albicans SC5314	Candida albicans SC5314	MIC	=	50.0	ug.mL-1	PMID[573433]
NPT1173	Organism	Candida albicans SC5314	Candida albicans SC5314	MIC	>	200.0	ug.mL-1	PMID[573433]

☑ 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 NPC471235 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	330
0.1-0.2	1454
0.2-0.3	4000
0.3-0.4	10845
0.4-0.5	8236
0.5-0.6	6546
0.6-0.7	10649
0.7-0.8	601
0.8-0.85	25
0.85-0.9	4
0.9-0.95	0
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC235033
1.0	High Similarity	NPC73132
0.8958	High Similarity	NPC81137
0.8933	High Similarity	NPC470710
0.8662	High Similarity	NPC11449
0.8533	High Similarity	NPC122599
0.8533	High Similarity	NPC272868
0.8533	High Similarity	NPC270848
0.8451	Intermediate Similarity	NPC78061
0.8451	Intermediate Similarity	NPC159987
0.8451	Intermediate Similarity	NPC122359
0.84	Intermediate Similarity	NPC147137
0.8239	Intermediate Similarity	NPC213414
0.8169	Intermediate Similarity	NPC105999
0.8133	Intermediate Similarity	NPC471236
0.8133	Intermediate Similarity	NPC197766
0.8099	Intermediate Similarity	NPC296202
0.8067	Intermediate Similarity	NPC177967
0.8067	Intermediate Similarity	NPC471237
0.8028	Intermediate Similarity	NPC7830
0.7972	Intermediate Similarity	NPC116562
0.7959	Intermediate Similarity	NPC478071
0.777	Intermediate Similarity	NPC2596
0.7762	Intermediate Similarity	NPC180207
0.76	Intermediate Similarity	NPC214246
0.7544	Intermediate Similarity	NPC470567
0.7535	Intermediate Similarity	NPC296526
0.7533	Intermediate Similarity	NPC219923
0.7485	Intermediate Similarity	NPC470566
0.7485	Intermediate Similarity	NPC300329
0.7483	Intermediate Similarity	NPC128249
0.7468	Intermediate Similarity	NPC184632
0.7468	Intermediate Similarity	NPC106406
0.7434	Intermediate Similarity	NPC12694
0.7423	Intermediate Similarity	NPC221091
0.7423	Intermediate Similarity	NPC259576
0.74	Intermediate Similarity	NPC474476
0.7386	Intermediate Similarity	NPC259017
0.7378	Intermediate Similarity	NPC243891
0.7375	Intermediate Similarity	NPC160378
0.7372	Intermediate Similarity	NPC223616
0.7365	Intermediate Similarity	NPC475697
0.7365	Intermediate Similarity	NPC471787
0.7361	Intermediate Similarity	NPC19290
0.7358	Intermediate Similarity	NPC188243
0.7358	Intermediate Similarity	NPC6407
0.7358	Intermediate Similarity	NPC110228
0.7349	Intermediate Similarity	NPC477299
0.7346	Intermediate Similarity	NPC473078
0.7346	Intermediate Similarity	NPC25844
0.7346	Intermediate Similarity	NPC470131
0.7346	Intermediate Similarity	NPC470132
0.7346	Intermediate Similarity	NPC470134
0.7346	Intermediate Similarity	NPC109183
0.7346	Intermediate Similarity	NPC470133
0.7342	Intermediate Similarity	NPC289690
0.7342	Intermediate Similarity	NPC251681
0.7342	Intermediate Similarity	NPC288452
0.7342	Intermediate Similarity	NPC243528
0.7338	Intermediate Similarity	NPC475008
0.7338	Intermediate Similarity	NPC186097
0.7338	Intermediate Similarity	NPC475009
0.7333	Intermediate Similarity	NPC267091
0.7333	Intermediate Similarity	NPC309512
0.7333	Intermediate Similarity	NPC4164
0.7333	Intermediate Similarity	NPC317715
0.7333	Intermediate Similarity	NPC148945
0.7333	Intermediate Similarity	NPC78835
0.7333	Intermediate Similarity	NPC316960
0.7333	Intermediate Similarity	NPC476434
0.7333	Intermediate Similarity	NPC204561
0.7329	Intermediate Similarity	NPC264976
0.7329	Intermediate Similarity	NPC223185
0.732	Intermediate Similarity	NPC469929
0.7317	Intermediate Similarity	NPC476684
0.7315	Intermediate Similarity	NPC473942
0.7312	Intermediate Similarity	NPC474385
0.7305	Intermediate Similarity	NPC131532
0.7305	Intermediate Similarity	NPC474535
0.7303	Intermediate Similarity	NPC79332
0.7301	Intermediate Similarity	NPC1580
0.7296	Intermediate Similarity	NPC136649
0.7296	Intermediate Similarity	NPC310370
0.7296	Intermediate Similarity	NPC310135
0.7296	Intermediate Similarity	NPC170812
0.7296	Intermediate Similarity	NPC265871
0.7296	Intermediate Similarity	NPC183642
0.7296	Intermediate Similarity	NPC9218
0.7296	Intermediate Similarity	NPC100675
0.7296	Intermediate Similarity	NPC470211
0.7296	Intermediate Similarity	NPC274784
0.7296	Intermediate Similarity	NPC329203
0.7296	Intermediate Similarity	NPC222342
0.7296	Intermediate Similarity	NPC225153
0.7296	Intermediate Similarity	NPC140890
0.7296	Intermediate Similarity	NPC150648
0.7296	Intermediate Similarity	NPC20709
0.7292	Intermediate Similarity	NPC51345
0.7285	Intermediate Similarity	NPC110211
0.7284	Intermediate Similarity	NPC39045
0.7284	Intermediate Similarity	NPC470136
0.7284	Intermediate Similarity	NPC291153
0.7284	Intermediate Similarity	NPC470135
0.7278	Intermediate Similarity	NPC188879
0.7273	Intermediate Similarity	NPC475460
0.7273	Intermediate Similarity	NPC87069
0.7273	Intermediate Similarity	NPC474735
0.7267	Intermediate Similarity	NPC220998
0.7267	Intermediate Similarity	NPC265040
0.7267	Intermediate Similarity	NPC324436
0.7267	Intermediate Similarity	NPC148757
0.7267	Intermediate Similarity	NPC221798
0.7267	Intermediate Similarity	NPC166934
0.7267	Intermediate Similarity	NPC227579
0.7267	Intermediate Similarity	NPC183824
0.7267	Intermediate Similarity	NPC78
0.7267	Intermediate Similarity	NPC223500
0.7267	Intermediate Similarity	NPC182852
0.7267	Intermediate Similarity	NPC228504
0.7267	Intermediate Similarity	NPC76372
0.7267	Intermediate Similarity	NPC40833
0.7267	Intermediate Similarity	NPC107572
0.7267	Intermediate Similarity	NPC177354
0.7267	Intermediate Similarity	NPC125855
0.7267	Intermediate Similarity	NPC64915
0.7267	Intermediate Similarity	NPC10937
0.7267	Intermediate Similarity	NPC324134
0.7267	Intermediate Similarity	NPC306829
0.7267	Intermediate Similarity	NPC1089
0.7267	Intermediate Similarity	NPC161506
0.7267	Intermediate Similarity	NPC37496
0.7267	Intermediate Similarity	NPC194432
0.7267	Intermediate Similarity	NPC296917
0.7267	Intermediate Similarity	NPC167624
0.7267	Intermediate Similarity	NPC76338
0.7267	Intermediate Similarity	NPC32739
0.7267	Intermediate Similarity	NPC166482
0.7267	Intermediate Similarity	NPC66515
0.7267	Intermediate Similarity	NPC328164
0.7261	Intermediate Similarity	NPC471345
0.726	Intermediate Similarity	NPC293424
0.726	Intermediate Similarity	NPC471033
0.726	Intermediate Similarity	NPC311091
0.7256	Intermediate Similarity	NPC476394
0.7256	Intermediate Similarity	NPC98809
0.725	Intermediate Similarity	NPC129853
0.725	Intermediate Similarity	NPC76445
0.725	Intermediate Similarity	NPC67467
0.725	Intermediate Similarity	NPC284550
0.7244	Intermediate Similarity	NPC192304
0.7244	Intermediate Similarity	NPC294593
0.7244	Intermediate Similarity	NPC18877
0.7244	Intermediate Similarity	NPC188646
0.7244	Intermediate Similarity	NPC175098
0.7244	Intermediate Similarity	NPC312318
0.7244	Intermediate Similarity	NPC82225
0.7244	Intermediate Similarity	NPC139813
0.7244	Intermediate Similarity	NPC135127
0.7244	Intermediate Similarity	NPC242294
0.7244	Intermediate Similarity	NPC20560
0.7244	Intermediate Similarity	NPC56031
0.7244	Intermediate Similarity	NPC263670
0.7244	Intermediate Similarity	NPC144051
0.7244	Intermediate Similarity	NPC472365
0.7244	Intermediate Similarity	NPC159623
0.7244	Intermediate Similarity	NPC337373
0.7244	Intermediate Similarity	NPC204960
0.7244	Intermediate Similarity	NPC28753
0.7239	Intermediate Similarity	NPC472629
0.7239	Intermediate Similarity	NPC178097
0.7239	Intermediate Similarity	NPC221383
0.7239	Intermediate Similarity	NPC283081
0.7239	Intermediate Similarity	NPC143892
0.7239	Intermediate Similarity	NPC228779
0.7239	Intermediate Similarity	NPC299090
0.7237	Intermediate Similarity	NPC264428
0.7233	Intermediate Similarity	NPC188947
0.7233	Intermediate Similarity	NPC124269
0.7233	Intermediate Similarity	NPC112789
0.7233	Intermediate Similarity	NPC99333
0.7233	Intermediate Similarity	NPC280284
0.7233	Intermediate Similarity	NPC19622
0.7233	Intermediate Similarity	NPC71903
0.7229	Intermediate Similarity	NPC295650
0.7229	Intermediate Similarity	NPC51198
0.7229	Intermediate Similarity	NPC290671
0.7226	Intermediate Similarity	NPC307289
0.7222	Intermediate Similarity	NPC471621
0.7222	Intermediate Similarity	NPC169591
0.7222	Intermediate Similarity	NPC51887
0.7222	Intermediate Similarity	NPC117836
0.7222	Intermediate Similarity	NPC277426
0.7222	Intermediate Similarity	NPC316816
0.7222	Intermediate Similarity	NPC280404
0.7222	Intermediate Similarity	NPC478086
0.7222	Intermediate Similarity	NPC85162
0.7222	Intermediate Similarity	NPC91560
0.7222	Intermediate Similarity	NPC164980
0.7222	Intermediate Similarity	NPC81697
0.7222	Intermediate Similarity	NPC475705

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 NPC471235 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	282
0.1-0.2	892
0.2-0.3	1689
0.3-0.4	2847
0.4-0.5	1947
0.5-0.6	1153
0.6-0.7	321
0.7-0.8	19
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7622	Intermediate Similarity	NPD4288	Approved
0.7622	Intermediate Similarity	NPD2296	Approved
0.7614	Intermediate Similarity	NPD4287	Approved
0.7484	Intermediate Similarity	NPD7033	Discontinued
0.7405	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6233	Phase 2
0.7329	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6798	Discontinued
0.732	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4628	Phase 3
0.7229	Intermediate Similarity	NPD7411	Suspended
0.7208	Intermediate Similarity	NPD3764	Approved
0.717	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7768	Phase 2
0.7125	Intermediate Similarity	NPD1549	Phase 2
0.7107	Intermediate Similarity	NPD2935	Discontinued
0.7105	Intermediate Similarity	NPD2797	Approved
0.7073	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1510	Phase 2
0.7027	Intermediate Similarity	NPD9545	Approved
0.7027	Intermediate Similarity	NPD1894	Discontinued
0.7018	Intermediate Similarity	NPD7075	Discontinued
0.7012	Intermediate Similarity	NPD6799	Approved
0.7006	Intermediate Similarity	NPD1240	Approved
0.7	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1551	Phase 2
0.6993	Remote Similarity	NPD1203	Approved
0.6988	Remote Similarity	NPD5403	Approved
0.6987	Remote Similarity	NPD3268	Approved
0.6982	Remote Similarity	NPD6801	Discontinued
0.697	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6832	Phase 2
0.6964	Remote Similarity	NPD4380	Phase 2
0.6962	Remote Similarity	NPD6355	Discontinued
0.6954	Remote Similarity	NPD1535	Discovery
0.6943	Remote Similarity	NPD4062	Phase 3
0.6941	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3750	Approved
0.6933	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3225	Approved
0.6918	Remote Similarity	NPD1607	Approved
0.6914	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1481	Phase 2
0.6894	Remote Similarity	NPD2796	Approved
0.689	Remote Similarity	NPD6190	Approved
0.6887	Remote Similarity	NPD3847	Discontinued
0.6875	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5401	Approved
0.6865	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4908	Phase 1
0.6849	Remote Similarity	NPD5535	Approved
0.6848	Remote Similarity	NPD7440	Discontinued
0.6842	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7819	Suspended
0.6842	Remote Similarity	NPD422	Phase 1
0.6839	Remote Similarity	NPD5647	Approved
0.6832	Remote Similarity	NPD2799	Discontinued
0.6826	Remote Similarity	NPD6273	Approved
0.6821	Remote Similarity	NPD6971	Discontinued
0.6821	Remote Similarity	NPD3749	Approved
0.6821	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD9717	Approved
0.6797	Remote Similarity	NPD1608	Approved
0.6784	Remote Similarity	NPD37	Approved
0.6784	Remote Similarity	NPD1934	Approved
0.678	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6166	Phase 2
0.6772	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6599	Discontinued
0.6763	Remote Similarity	NPD4966	Approved
0.6763	Remote Similarity	NPD4965	Approved
0.6763	Remote Similarity	NPD4967	Phase 2
0.6761	Remote Similarity	NPD6232	Discontinued
0.675	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5124	Phase 1
0.675	Remote Similarity	NPD4340	Discontinued
0.6748	Remote Similarity	NPD6002	Phase 3
0.6748	Remote Similarity	NPD6004	Phase 3
0.6748	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6005	Phase 3
0.6748	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD8455	Phase 2
0.674	Remote Similarity	NPD6559	Discontinued
0.6727	Remote Similarity	NPD7003	Approved
0.6725	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD9718	Approved
0.6707	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD3817	Phase 2
0.6705	Remote Similarity	NPD5402	Approved
0.6689	Remote Similarity	NPD1548	Phase 1
0.6689	Remote Similarity	NPD1241	Discontinued
0.6686	Remote Similarity	NPD6234	Discontinued
0.6686	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD3134	Approved
0.6667	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD2532	Approved
0.6667	Remote Similarity	NPD2533	Approved
0.6667	Remote Similarity	NPD9493	Approved
0.6667	Remote Similarity	NPD2534	Approved
0.6667	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3267	Approved
0.6667	Remote Similarity	NPD5844	Phase 1
0.6648	Remote Similarity	NPD7473	Discontinued
0.6647	Remote Similarity	NPD2801	Approved
0.6646	Remote Similarity	NPD2344	Approved
0.6646	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7266	Discontinued
0.6627	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD4308	Phase 3
0.6626	Remote Similarity	NPD3748	Approved
0.6624	Remote Similarity	NPD2798	Approved
0.6623	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD1358	Approved
0.6611	Remote Similarity	NPD3818	Discontinued
0.661	Remote Similarity	NPD7199	Phase 2
0.661	Remote Similarity	NPD6959	Discontinued
0.6608	Remote Similarity	NPD3226	Approved
0.6607	Remote Similarity	NPD1511	Approved
0.6604	Remote Similarity	NPD3027	Phase 3
0.6604	Remote Similarity	NPD7095	Approved
0.6603	Remote Similarity	NPD1283	Approved
0.6601	Remote Similarity	NPD17	Approved
0.6588	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4140	Approved
0.6582	Remote Similarity	NPD2861	Phase 2
0.6575	Remote Similarity	NPD7054	Approved
0.6575	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD1652	Phase 2
0.6564	Remote Similarity	NPD7097	Phase 1
0.6561	Remote Similarity	NPD6362	Approved
0.6543	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD1933	Approved
0.6541	Remote Similarity	NPD2614	Approved
0.6538	Remote Similarity	NPD6582	Phase 2
0.6538	Remote Similarity	NPD7074	Phase 3
0.6538	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6583	Phase 3
0.6538	Remote Similarity	NPD7472	Approved
0.6529	Remote Similarity	NPD1512	Approved
0.6527	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD4110	Phase 3
0.6522	Remote Similarity	NPD6663	Approved
0.6522	Remote Similarity	NPD4870	Approved
0.6522	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7228	Approved
0.6517	Remote Similarity	NPD8127	Discontinued
0.6516	Remote Similarity	NPD1610	Phase 2
0.6512	Remote Similarity	NPD7458	Discontinued
0.6506	Remote Similarity	NPD4534	Discontinued
0.6506	Remote Similarity	NPD5958	Discontinued
0.6503	Remote Similarity	NPD6653	Approved
0.6503	Remote Similarity	NPD6797	Phase 2
0.6503	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD1778	Approved
0.6488	Remote Similarity	NPD2309	Approved
0.6486	Remote Similarity	NPD8312	Approved
0.6486	Remote Similarity	NPD8313	Approved
0.6485	Remote Similarity	NPD5404	Approved
0.6485	Remote Similarity	NPD5408	Approved
0.6485	Remote Similarity	NPD4476	Approved
0.6485	Remote Similarity	NPD5406	Approved
0.6485	Remote Similarity	NPD4477	Approved
0.6485	Remote Similarity	NPD2438	Suspended
0.6485	Remote Similarity	NPD5405	Approved
0.6483	Remote Similarity	NPD5048	Discontinued
0.6481	Remote Similarity	NPD4060	Phase 1
0.6481	Remote Similarity	NPD2979	Phase 3
0.648	Remote Similarity	NPD7229	Phase 3
0.6478	Remote Similarity	NPD5736	Approved
0.6474	Remote Similarity	NPD6502	Phase 2
0.6474	Remote Similarity	NPD3972	Approved
0.6467	Remote Similarity	NPD7038	Approved
0.6467	Remote Similarity	NPD7685	Pre-registration
0.6467	Remote Similarity	NPD7039	Approved
0.6467	Remote Similarity	NPD7251	Discontinued
0.6463	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.646	Remote Similarity	NPD1296	Phase 2
0.6452	Remote Similarity	NPD3496	Discontinued
0.6446	Remote Similarity	NPD2346	Discontinued
0.6446	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD230	Phase 1
0.6432	Remote Similarity	NPD7808	Phase 3
0.6432	Remote Similarity	NPD2802	Phase 3
0.6429	Remote Similarity	NPD5585	Approved
0.6429	Remote Similarity	NPD8166	Discontinued
0.642	Remote Similarity	NPD8032	Phase 2
0.6419	Remote Similarity	NPD5451	Approved
0.6417	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD1019	Discontinued
0.6415	Remote Similarity	NPD6584	Phase 3
0.6415	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD5953	Discontinued

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