NPASS Compound

Structure

NPC108948 OpenBabel07101719252D 35 38 0 0 1 0 0 0 0 0999 V2000 0.8438 -5.3590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8625 0.8438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8881 0.8438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3310 1.3310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3566 1.3310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5571 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -4.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -3.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2191 -0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6876 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0629 -0.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 0.4872 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -1.9487 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -4.3846 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -4.3846 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0443 -2.3054 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 12 1 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 24 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 11 17 1 0 0 0 0 11 25 1 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 30 1 0 0 0 0 15 22 1 0 0 0 0 15 24 1 1 0 0 0 16 22 1 0 0 0 0 16 27 1 1 0 0 0 17 23 1 0 0 0 0 17 28 1 1 0 0 0 18 19 2 0 0 0 0 18 21 1 0 0 0 0 19 31 1 0 0 0 0 20 26 1 0 0 0 0 20 32 2 0 0 0 0 21 25 1 0 0 0 0 21 33 2 0 0 0 0 23 35 1 0 0 0 0 24 6 1 1 0 0 0 24 34 1 0 0 0 0 25 26 1 6 0 0 0 25 29 1 0 0 0 0 26 10 1 6 0 0 0 26 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.13
Volume:	509.219
LogP:	5.971
LogD:	3.991
LogS:	-3.989
# Rotatable Bonds:	2
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.423
Synthetic Accessibility Score:	5.261
Fsp3:	0.692
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.84
MDCK Permeability:	1.7601692889002152e-05
Pgp-inhibitor:	0.874
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.057
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.831
Plasma Protein Binding (PPB):	100.49459075927734%
Volume Distribution (VD):	1.941
Pgp-substrate:	2.9165329933166504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.118
CYP1A2-substrate:	0.909
CYP2C19-inhibitor:	0.289
CYP2C19-substrate:	0.772
CYP2C9-inhibitor:	0.715
CYP2C9-substrate:	0.662
CYP2D6-inhibitor:	0.185
CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	0.692
CYP3A4-substrate:	0.836

ADMET: Excretion

Clearance (CL):	6.612
Half-life (T1/2):	0.04

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.301
Drug-inuced Liver Injury (DILI):	0.313
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.489
Maximum Recommended Daily Dose:	0.842
Skin Sensitization:	0.306
Carcinogencity:	0.646
Eye Corrosion:	0.004
Eye Irritation:	0.465
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC108948

Natural Product ID:	NPC108948
*Common Name:**	(3R,4Ar,10As)-3,4A-Dichloro-10A-[[(1S,3S,6S)-3-Chloro-6-Hydroxy-2,2,6-Trimethylcyclohexyl]Methyl]-6,8-Dihydroxy-2,2,7-Trimethyl-3,4-Dihydrobenzo[G]Chromene-5,10-Dione
IUPAC Name:	(3R,4aR,10aS)-3,4a-dichloro-10a-[[(1S,3S,6S)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl]-6,8-dihydroxy-2,2,7-trimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione
Synonyms:
Standard InCHIKey:	XGGIVXWAYKZBIV-CYGDAPSSSA-N
Standard InCHI:	InChI=1S/C26H33Cl3O6/c1-12-14(30)9-13-18(19(12)31)21(33)25(29)11-17(28)23(4,5)35-26(25,20(13)32)10-15-22(2,3)16(27)7-8-24(15,6)34/h9,15-17,30-31,34H,7-8,10-11H2,1-6H3/t15-,16-,17+,24-,25-,26-/m0/s1
SMILES:	Cc1c(cc2c(c1O)C(=O)[C@]1(C[C@H](C(C)(C)O[C@@]1(C[C@H]1C(C)(C)[C@H](CC[C@]1(C)O)Cl)C2=O)Cl)Cl)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3104877
PubChem CID:	14650471
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO32475	actinomycete sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24328269]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	15000.0	nM	PMID[570887]

☑ 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 NPC108948 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	494
0.1-0.2	1963
0.2-0.3	4098
0.3-0.4	10563
0.4-0.5	9885
0.5-0.6	6367
0.6-0.7	8001
0.7-0.8	1305
0.8-0.85	7
0.85-0.9	4
0.9-0.95	4
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC301846
0.9748	High Similarity	NPC311679
0.9748	High Similarity	NPC131078
0.9627	High Similarity	NPC184518
0.9394	High Similarity	NPC471684
0.9321	High Similarity	NPC73544
0.9162	High Similarity	NPC158699
0.897	High Similarity	NPC471685
0.8889	High Similarity	NPC471686
0.8462	Intermediate Similarity	NPC471687
0.8214	Intermediate Similarity	NPC470564
0.814	Intermediate Similarity	NPC470563
0.8118	Intermediate Similarity	NPC470559
0.8081	Intermediate Similarity	NPC470561
0.8075	Intermediate Similarity	NPC181560
0.8075	Intermediate Similarity	NPC169452
0.8012	Intermediate Similarity	NPC138099
0.8012	Intermediate Similarity	NPC242994
0.8	Intermediate Similarity	NPC471905
0.7989	Intermediate Similarity	NPC316262
0.7989	Intermediate Similarity	NPC314653
0.7988	Intermediate Similarity	NPC471906
0.7977	Intermediate Similarity	NPC475106
0.7975	Intermediate Similarity	NPC193555
0.7937	Intermediate Similarity	NPC254847
0.7937	Intermediate Similarity	NPC191976
0.7914	Intermediate Similarity	NPC246638
0.791	Intermediate Similarity	NPC277865
0.791	Intermediate Similarity	NPC470565
0.791	Intermediate Similarity	NPC470562
0.791	Intermediate Similarity	NPC474004
0.7901	Intermediate Similarity	NPC143438
0.7892	Intermediate Similarity	NPC470570
0.7888	Intermediate Similarity	NPC53414
0.7888	Intermediate Similarity	NPC53206
0.7877	Intermediate Similarity	NPC264922
0.7866	Intermediate Similarity	NPC308572
0.7866	Intermediate Similarity	NPC135524
0.7866	Intermediate Similarity	NPC474961
0.7865	Intermediate Similarity	NPC470560
0.7849	Intermediate Similarity	NPC197326
0.7849	Intermediate Similarity	NPC201127
0.7849	Intermediate Similarity	NPC272196
0.7849	Intermediate Similarity	NPC474637
0.7844	Intermediate Similarity	NPC37709
0.7841	Intermediate Similarity	NPC125465
0.7831	Intermediate Similarity	NPC34482
0.7809	Intermediate Similarity	NPC315306
0.7809	Intermediate Similarity	NPC313717
0.7805	Intermediate Similarity	NPC110810
0.7805	Intermediate Similarity	NPC204045
0.7805	Intermediate Similarity	NPC305845
0.7803	Intermediate Similarity	NPC472617
0.7791	Intermediate Similarity	NPC190457
0.7791	Intermediate Similarity	NPC280497
0.7778	Intermediate Similarity	NPC472211
0.7778	Intermediate Similarity	NPC53001
0.7771	Intermediate Similarity	NPC244691
0.7771	Intermediate Similarity	NPC48762
0.7771	Intermediate Similarity	NPC21599
0.7771	Intermediate Similarity	NPC193703
0.7765	Intermediate Similarity	NPC305965
0.7765	Intermediate Similarity	NPC474857
0.7759	Intermediate Similarity	NPC472618
0.7759	Intermediate Similarity	NPC313368
0.7753	Intermediate Similarity	NPC54903
0.7753	Intermediate Similarity	NPC286074
0.775	Intermediate Similarity	NPC267205
0.7738	Intermediate Similarity	NPC312929
0.7738	Intermediate Similarity	NPC126767
0.7738	Intermediate Similarity	NPC190648
0.7738	Intermediate Similarity	NPC56433
0.7738	Intermediate Similarity	NPC245584
0.7738	Intermediate Similarity	NPC289042
0.7738	Intermediate Similarity	NPC118027
0.773	Intermediate Similarity	NPC87723
0.7727	Intermediate Similarity	NPC100849
0.7725	Intermediate Similarity	NPC28632
0.7725	Intermediate Similarity	NPC470674
0.7725	Intermediate Similarity	NPC12402
0.7725	Intermediate Similarity	NPC470673
0.7725	Intermediate Similarity	NPC117716
0.7725	Intermediate Similarity	NPC474630
0.7722	Intermediate Similarity	NPC303910
0.7719	Intermediate Similarity	NPC154683
0.7719	Intermediate Similarity	NPC142527
0.7719	Intermediate Similarity	NPC40356
0.7716	Intermediate Similarity	NPC474311
0.7714	Intermediate Similarity	NPC103816
0.7714	Intermediate Similarity	NPC61382
0.7714	Intermediate Similarity	NPC219686
0.7711	Intermediate Similarity	NPC474203
0.7711	Intermediate Similarity	NPC451542
0.7711	Intermediate Similarity	NPC313047
0.7711	Intermediate Similarity	NPC174905
0.7711	Intermediate Similarity	NPC295712
0.7711	Intermediate Similarity	NPC293545
0.7706	Intermediate Similarity	NPC470568
0.7706	Intermediate Similarity	NPC147735
0.7706	Intermediate Similarity	NPC294646
0.7705	Intermediate Similarity	NPC151292
0.7702	Intermediate Similarity	NPC166480
0.7702	Intermediate Similarity	NPC282780
0.7702	Intermediate Similarity	NPC44437
0.7697	Intermediate Similarity	NPC290550
0.7692	Intermediate Similarity	NPC142846
0.7692	Intermediate Similarity	NPC94781
0.7688	Intermediate Similarity	NPC4547
0.7679	Intermediate Similarity	NPC271944
0.7679	Intermediate Similarity	NPC85393
0.7679	Intermediate Similarity	NPC473135
0.7679	Intermediate Similarity	NPC470676
0.7679	Intermediate Similarity	NPC110882
0.7679	Intermediate Similarity	NPC136878
0.7679	Intermediate Similarity	NPC473132
0.7676	Intermediate Similarity	NPC191606
0.7674	Intermediate Similarity	NPC214632
0.7674	Intermediate Similarity	NPC470408
0.7674	Intermediate Similarity	NPC182921
0.7674	Intermediate Similarity	NPC218870
0.7674	Intermediate Similarity	NPC474824
0.7673	Intermediate Similarity	NPC108129
0.767	Intermediate Similarity	NPC245122
0.7667	Intermediate Similarity	NPC118128
0.7665	Intermediate Similarity	NPC227841
0.7661	Intermediate Similarity	NPC470569
0.7661	Intermediate Similarity	NPC478148
0.7654	Intermediate Similarity	NPC249272
0.7647	Intermediate Similarity	NPC477566
0.7647	Intermediate Similarity	NPC477567
0.7647	Intermediate Similarity	NPC329933
0.7647	Intermediate Similarity	NPC474310
0.7647	Intermediate Similarity	NPC120171
0.7644	Intermediate Similarity	NPC158542
0.764	Intermediate Similarity	NPC476056
0.764	Intermediate Similarity	NPC17274
0.764	Intermediate Similarity	NPC85047
0.764	Intermediate Similarity	NPC120857
0.7633	Intermediate Similarity	NPC34802
0.7633	Intermediate Similarity	NPC5568
0.763	Intermediate Similarity	NPC226656
0.763	Intermediate Similarity	NPC275575
0.763	Intermediate Similarity	NPC66508
0.7624	Intermediate Similarity	NPC470422
0.7624	Intermediate Similarity	NPC469393
0.7622	Intermediate Similarity	NPC13715
0.7616	Intermediate Similarity	NPC45934
0.7616	Intermediate Similarity	NPC470353
0.7605	Intermediate Similarity	NPC471682
0.7605	Intermediate Similarity	NPC100242
0.7602	Intermediate Similarity	NPC315520
0.7602	Intermediate Similarity	NPC255641
0.7602	Intermediate Similarity	NPC205766
0.7602	Intermediate Similarity	NPC290954
0.76	Intermediate Similarity	NPC324736
0.76	Intermediate Similarity	NPC228654
0.76	Intermediate Similarity	NPC239118
0.7598	Intermediate Similarity	NPC76647
0.7598	Intermediate Similarity	NPC193222
0.7596	Intermediate Similarity	NPC470334
0.7593	Intermediate Similarity	NPC12070
0.7593	Intermediate Similarity	NPC270899
0.7593	Intermediate Similarity	NPC202225
0.759	Intermediate Similarity	NPC92079
0.7588	Intermediate Similarity	NPC112816
0.7586	Intermediate Similarity	NPC474861
0.7586	Intermediate Similarity	NPC192587
0.7586	Intermediate Similarity	NPC470352
0.7586	Intermediate Similarity	NPC470354
0.7584	Intermediate Similarity	NPC472049
0.7576	Intermediate Similarity	NPC114620
0.7576	Intermediate Similarity	NPC103337
0.7574	Intermediate Similarity	NPC143685
0.7574	Intermediate Similarity	NPC285122
0.7572	Intermediate Similarity	NPC178964
0.7572	Intermediate Similarity	NPC280530
0.7572	Intermediate Similarity	NPC95842
0.7572	Intermediate Similarity	NPC329844
0.7571	Intermediate Similarity	NPC470694
0.7571	Intermediate Similarity	NPC473022
0.7571	Intermediate Similarity	NPC94796
0.756	Intermediate Similarity	NPC19896
0.756	Intermediate Similarity	NPC10764
0.756	Intermediate Similarity	NPC29932
0.7558	Intermediate Similarity	NPC149526
0.7558	Intermediate Similarity	NPC474417
0.7558	Intermediate Similarity	NPC470675
0.7558	Intermediate Similarity	NPC473131
0.7558	Intermediate Similarity	NPC230848
0.7557	Intermediate Similarity	NPC284495
0.7557	Intermediate Similarity	NPC472052
0.7557	Intermediate Similarity	NPC470342
0.7557	Intermediate Similarity	NPC472060
0.7556	Intermediate Similarity	NPC20734
0.7546	Intermediate Similarity	NPC290803
0.7546	Intermediate Similarity	NPC283088
0.7545	Intermediate Similarity	NPC257644
0.7545	Intermediate Similarity	NPC73061
0.7545	Intermediate Similarity	NPC291078
0.7544	Intermediate Similarity	NPC65775

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 NPC108948 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	1046
0.2-0.3	1938
0.3-0.4	3192
0.4-0.5	1790
0.5-0.6	565
0.6-0.7	211
0.7-0.8	8
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
0.7937	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7390	Discontinued
0.7416	Intermediate Similarity	NPD6959	Discontinued
0.7348	Intermediate Similarity	NPD7473	Discontinued
0.7209	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6232	Discontinued
0.7175	Intermediate Similarity	NPD7819	Suspended
0.7173	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5406	Approved
0.7143	Intermediate Similarity	NPD1470	Approved
0.7143	Intermediate Similarity	NPD5408	Approved
0.7143	Intermediate Similarity	NPD5405	Approved
0.7143	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD6100	Approved
0.7143	Intermediate Similarity	NPD5404	Approved
0.7135	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD2533	Approved
0.711	Intermediate Similarity	NPD2532	Approved
0.711	Intermediate Similarity	NPD2534	Approved
0.7083	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7075	Discontinued
0.7053	Intermediate Similarity	NPD8150	Discontinued
0.7018	Intermediate Similarity	NPD2800	Approved
0.7011	Intermediate Similarity	NPD2403	Approved
0.7006	Intermediate Similarity	NPD4380	Phase 2
0.6983	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD3749	Approved
0.6959	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3226	Approved
0.6946	Remote Similarity	NPD943	Approved
0.6914	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6599	Discontinued
0.6894	Remote Similarity	NPD1201	Approved
0.6872	Remote Similarity	NPD7411	Suspended
0.6866	Remote Similarity	NPD8320	Phase 1
0.6866	Remote Similarity	NPD8319	Approved
0.6864	Remote Similarity	NPD6651	Approved
0.6864	Remote Similarity	NPD1607	Approved
0.6837	Remote Similarity	NPD6535	Approved
0.6837	Remote Similarity	NPD6534	Approved
0.6828	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6166	Phase 2
0.6828	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD6784	Approved
0.6823	Remote Similarity	NPD6785	Approved
0.6818	Remote Similarity	NPD7700	Phase 2
0.6818	Remote Similarity	NPD7699	Phase 2
0.6816	Remote Similarity	NPD7435	Discontinued
0.6813	Remote Similarity	NPD3882	Suspended
0.6809	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5844	Phase 1
0.68	Remote Similarity	NPD3300	Phase 2
0.6793	Remote Similarity	NPD5494	Approved
0.6784	Remote Similarity	NPD1510	Phase 2
0.678	Remote Similarity	NPD1512	Approved
0.6763	Remote Similarity	NPD1549	Phase 2
0.675	Remote Similarity	NPD6780	Approved
0.675	Remote Similarity	NPD6778	Approved
0.675	Remote Similarity	NPD6779	Approved
0.675	Remote Similarity	NPD6777	Approved
0.675	Remote Similarity	NPD6782	Approved
0.675	Remote Similarity	NPD6781	Approved
0.675	Remote Similarity	NPD6776	Approved
0.6746	Remote Similarity	NPD1240	Approved
0.674	Remote Similarity	NPD1934	Approved
0.674	Remote Similarity	NPD6801	Discontinued
0.6738	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7698	Approved
0.6733	Remote Similarity	NPD7696	Phase 3
0.6733	Remote Similarity	NPD7697	Approved
0.6721	Remote Similarity	NPD7768	Phase 2
0.672	Remote Similarity	NPD5711	Approved
0.672	Remote Similarity	NPD5710	Approved
0.6705	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2346	Discontinued
0.6703	Remote Similarity	NPD2801	Approved
0.67	Remote Similarity	NPD7870	Phase 2
0.67	Remote Similarity	NPD7871	Phase 2
0.6686	Remote Similarity	NPD3750	Approved
0.6686	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4363	Phase 3
0.6667	Remote Similarity	NPD1511	Approved
0.6667	Remote Similarity	NPD4360	Phase 2
0.663	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7874	Approved
0.6618	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD7251	Discontinued
0.6612	Remote Similarity	NPD1465	Phase 2
0.6602	Remote Similarity	NPD7701	Phase 2
0.6595	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7801	Approved
0.658	Remote Similarity	NPD7808	Phase 3
0.6579	Remote Similarity	NPD3751	Discontinued
0.6576	Remote Similarity	NPD3817	Phase 2
0.6573	Remote Similarity	NPD6799	Approved
0.657	Remote Similarity	NPD8151	Discontinued
0.6564	Remote Similarity	NPD3019	Approved
0.6562	Remote Similarity	NPD6797	Phase 2
0.6552	Remote Similarity	NPD2796	Approved
0.6552	Remote Similarity	NPD2935	Discontinued
0.6546	Remote Similarity	NPD8313	Approved
0.6546	Remote Similarity	NPD8312	Approved
0.6529	Remote Similarity	NPD3764	Approved
0.6528	Remote Similarity	NPD6559	Discontinued
0.6522	Remote Similarity	NPD405	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7074	Phase 3
0.6505	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD7003	Approved
0.6495	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5402	Approved
0.6484	Remote Similarity	NPD7458	Discontinued
0.648	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD2932	Approved
0.6458	Remote Similarity	NPD6020	Phase 2
0.6458	Remote Similarity	NPD7054	Approved
0.6447	Remote Similarity	NPD8434	Phase 2
0.6425	Remote Similarity	NPD7236	Approved
0.6425	Remote Similarity	NPD7472	Approved
0.6416	Remote Similarity	NPD230	Phase 1
0.6406	Remote Similarity	NPD3818	Discontinued
0.6404	Remote Similarity	NPD4975	Approved
0.6404	Remote Similarity	NPD8166	Discontinued
0.6404	Remote Similarity	NPD4974	Approved
0.64	Remote Similarity	NPD3748	Approved
0.64	Remote Similarity	NPD2799	Discontinued
0.6393	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4361	Phase 2
0.6386	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4625	Phase 3
0.6373	Remote Similarity	NPD5544	Approved
0.6373	Remote Similarity	NPD7286	Phase 2
0.6369	Remote Similarity	NPD6190	Approved
0.6368	Remote Similarity	NPD6212	Phase 3
0.6368	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD3787	Discontinued
0.6368	Remote Similarity	NPD6213	Phase 3
0.6359	Remote Similarity	NPD6823	Phase 2
0.6354	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD4878	Approved
0.6344	Remote Similarity	NPD5760	Phase 2
0.6344	Remote Similarity	NPD5761	Phase 2
0.6341	Remote Similarity	NPD4914	Approved
0.6339	Remote Similarity	NPD7239	Suspended
0.6337	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD3926	Phase 2
0.6331	Remote Similarity	NPD1164	Approved
0.6328	Remote Similarity	NPD2344	Approved
0.6328	Remote Similarity	NPD1471	Phase 3
0.6316	Remote Similarity	NPD1247	Approved
0.6313	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD5953	Discontinued
0.6301	Remote Similarity	NPD6663	Approved
0.6284	Remote Similarity	NPD5403	Approved
0.6284	Remote Similarity	NPD920	Approved
0.6283	Remote Similarity	NPD7229	Phase 3
0.628	Remote Similarity	NPD4387	Approved
0.628	Remote Similarity	NPD4386	Approved
0.6271	Remote Similarity	NPD1551	Phase 2
0.6262	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD1243	Approved
0.6257	Remote Similarity	NPD5736	Approved
0.625	Remote Similarity	NPD9269	Phase 2
0.6244	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD7799	Discontinued
0.6237	Remote Similarity	NPD7228	Approved
0.6228	Remote Similarity	NPD4879	Approved
0.6228	Remote Similarity	NPD3026	Approved
0.6228	Remote Similarity	NPD3023	Approved
0.6222	Remote Similarity	NPD4628	Phase 3
0.6219	Remote Similarity	NPD4287	Approved
0.6213	Remote Similarity	NPD4749	Approved
0.6211	Remote Similarity	NPD6234	Discontinued
0.6211	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD919	Approved
0.6207	Remote Similarity	NPD7961	Discontinued
0.6205	Remote Similarity	NPD3025	Approved
0.6205	Remote Similarity	NPD9268	Approved
0.6205	Remote Similarity	NPD3024	Approved
0.6203	Remote Similarity	NPD37	Approved
0.6197	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD7783	Phase 2
0.6195	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5543	Approved
0.6195	Remote Similarity	NPD4388	Approved
0.6195	Remote Similarity	NPD4915	Approved
0.6193	Remote Similarity	NPD5027	Approved
0.6193	Remote Similarity	NPD5029	Approved
0.6193	Remote Similarity	NPD5031	Approved
0.619	Remote Similarity	NPD4967	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